Case 15-1815 Document 30 01 12 2016 1682738 Page1 of 170 15-1815- CR IN THE United States Court of Appeals FOR THE SECOND CIRCUIT UNITED STATES OF AMERICA Appellee v ROSS WILLIAM ULBRICHT AKA DREAD PIRATE ROBERTS AKA SILK ROAD AKA SEALED DEFENDANT 1 AKA DPR Defendant-Appellant On Appeal from the United States District Court for the Southern District of New York New York City BRIEF FOR DEFENDANT-APPELLANT JOSHUA L DRATEL P C Attorneys for Defendant-Appellant 29 Broadway Suite 1412 New York New York 10006 212-732-0707 Case 15-1815 Document 30 01 12 2016 1682738 Page2 of 170 TABLE OF CONTENTS TABLE OF AUTHORITIES vii JURISDICTIONAL STATEMENT 1 STATEMENT OF THE ISSUES 1 SUMMARY OF THE ARGUMENT 3 STATEMENT OF THE CASE 8 A The Charges 9 B Pretrial Motions 10 C Disclosure of Force's Corruption During the Investigation 11 D The Trial 13 E The Charge and Verdict 17 F Post-Trial Motions and Further Disclosure Regarding Corruption In the Investigation 18 G Sentencing 18 ARGUMENT 20 POINT I THE COURT ABUSED ITS DISCRETION AND DENIED ULBRICHT HIS FIFTH AND SIXTH AMENDMENT RIGHTS TO DUE PROCESS THE RIGHT TO PRESENT A DEFENSE AND A FAIR TRIAL BY A PRECLUDING THE DEFENSE FROM USING AT TRIAL THE EVIDENCE RELATING TO DEA SPECIAL AGENT CARL FORCE'S CORRUPTION B REFUSING TO ORDER THE GOVERNMENT TO PROVIDE ADDITIONAL DISCOVERY AND BRADY MATERIAL REGARDING CORRUPTION AND C DENYING ULBRICHT'S MOTION FOR A NEW TRIAL BASED ON ADDITIONAL POST-TRIAL DISCLOSURES REGARDING FORCE AND ANOTHER CORRUPT LAW ENFORCEMENT AGENT INVOLVED IN THE SILK ROAD INVESTIGATION 20 i Case 15-1815 Document 30 01 12 2016 1682738 Page3 of 170 A The Government's Eve-of-Trial Disclosure of Force's Corruption 23 B The Court's Further Preclusion at Trial of Evidence the Pretrial Rulings Had Permitted the Defense to Use 27 1 C The Post-Trial Revelation of Bridges's Corruption and the Additional Post-Trial Disclosures of Force's Misconduct 30 The Court Abused Its Discretion In Precluding Ulbricht from Utilizing at Trial Information Related to Force's Corruption 37 1 There Was Not Sufficient Need to Maintain Secrecy of the Investigation of Force and Bridges to Ulbricht's Detriment In This Case 39 2 The Record Demonstrates That Silk Road Investigations Were Coordinated and Combined 40 3 The Information Regarding the Investigation of Force and Bridges Is Relevant to This Case Regardless Whether the Investigations Were Independent 46 a The Government's Initial Exhibit List 46 b The Importance of the First Half of 2013 Regarding the Evidence At Trial 47 D The Court Abused Its Discretion By Deviating From Its Pretrial Ruling and Precluding Evidence That It Had Determined Would Be Admissible 48 E The Court Abused Its Discretion In Denying Ulbricht's Motion for a New Trial Based on the Government's Failure to Make Complete and Accurate Pretrial Disclosure Regarding Law Enforcement Corruption In the Government's Investigation 50 1 The Principles Applicable to Exculpatory Material and Information 50 a General Principles Governing the Government's Brady Disclosure Obligations 50 ii Case 15-1815 Document 30 01 12 2016 1682738 Page4 of 170 b 2 The Manner of the Government's Brady Disclosure Obligations 59 The Government Failed to Make Timely Production of Exculpatory Material 60 POINT II THE COURT ABUSED ITS DISCRETION BY CURTAILING CROSS-EXAMINATION AND THE DEFENSE THEORY AT TRIAL 63 A HSI SA Jared Der Yeghiayan 63 1 In Curtailing and Striking Cross Examination of SA Der-Yeghiayan the Court Improperly Concluded There Was No Nexus Between the Alternative Perpetrator and the Specific Offenses 66 a Relevant Case Law Regarding An Alternate Perpetrator 66 b The Requisite Nexus Was Established By the Government Itself Through Its Direct Examination of SA Der-Yeghiayan 69 2 The Court Also Erred by Disregarding the Untimeliness of the Government's Objections Failing to Acknowledge That Cross Examination of SA Der-Yeghiayan Was Relevant to Another Proper Defense Ulbricht Was Presenting and Improperly Considering Issues Regarding the Government's Possible Redirect 70 3 The Court Abused Its Discretion by Precluding the Defense From Eliciting from SA Der-Yeghiayan that Karpeles Attempted to Exchange Immunity for the Identity of DPR 71 B FBI Computer Specialist Thomas Kiernan 75 C The Court's Rulings Which Curtailed the Cross Examinations of SA Der-Yeghiayan and Agent Kiernan Constituted an Abuse of Discretion 76 iii Case 15-1815 Document 30 01 12 2016 1682738 Page5 of 170 POINT III THE COURT ABUSED ITS DISCRETION IN PRECLUDING TWO DEFENSE EXPERTS 78 A The Court's Decision Precluding the Two Defense Experts 80 B The Court Abused Its Discretion In Precluding the Two Defense Experts 83 POINT IV THE COURT ABUSED ITS DISCRETION IN PRECLUDING ADMISSION OF ANDREW JONES'S STATEMENT AGAINST PENAL INTEREST PURSUANT TO RULE 804 3 b FED R EVID AND OR RULE 807 FED R EVID 90 A Pretrial Disclosure of Andrew Jones's Exculpatory Statement 90 B The Trial Proceedings 91 C The Court Abused Its Discretion In Precluding Admission of Jones's Statement Under Either Rule 804 3 b or Rule 807 92 POINT V THE COURT'S ERRONEOUS EVIDENTIARY RULINGS CONSTITUTED CUMULATIVE ERROR THAT DEPRIVED ULBRICHT OF DUE PROCESS AND A FAIR TRIAL 97 POINT VI THE UNLIMITED SEARCHES AND SEIZURE OF ULBRICHT'S ENTIRE LAPTOP AND GMAIL AND FACEBOOK ACCOUNTS VIOLATED THE FOURTH AMENDMENT BECAUSE THEY CONSTITUTED THE FRUIT OF A A WARRANT THAT LACKED ANY PARTICULARITY AND B UNLAWFUL AND WARRANTLESS PEN REGISTER AND TRAP AND TRACE ORDERS 98 A The Search of Ulbricht's Laptop and Gmail and Facebook Accounts Violated the Fourth Amendment Because the Warrant Authorizing the Search Lacked Any Particularity 98 iv Case 15-1815 Document 30 01 12 2016 1682738 Page6 of 170 B 1 The Unlimited Scope of the Warrants At Issue 98 2 The Court's Rationale for Denying Ulbricht's Motion to Suppress 100 3 The Overriding Importance of the Particularity Requirement 100 4 The Warrants At Issue Are Devoid of Particularity 102 The Pen Register and Trap and Trace Orders Were Unlawful and Violated the Fourth Amendment Because They Required a Warrant and Also Failed to Adhere to Statutory Limitations 109 1 The Pen Register and Trap and Trace Orders Were Unlawful Because They Required a Warrant 109 a Smith v Maryland Does Not Control the Issue Herein 111 b The Pen-Trap Devices In This Case Required a Warrant Because They Captured Information About Ulbricht's Activities In His Home 118 c 2 The Pen-Trap Devices In This Case Required a Warrant and or Violated the Operative Statute Because They Captured Prospective Data and Information 120 The Pen Register and Trap and Trace Devices Used In This Case Were Unlawful Because They Exceeded Statutory Authority 121 POINT VII THE LIFE SENTENCE IMPOSED ON ULBRICHT WAS PROCEDURALLY AND SUBSTANTIVELY UNREASONABLE 125 A The Life Sentence Was Procedurally Unreasonable 125 1 The Court Erred In Considering the Alleged Overdose Deaths Based on An Entirely Subjective Undefined and Unprecedented Standard 127 v Case 15-1815 Document 30 01 12 2016 1682738 Page7 of 170 2 The Court Improperly Relied on the Alleged Overdose Deaths Purportedly Attributable to the Silk Road Site Without Sufficient or Reliable Proof 128 a The Relevant Case Law 128 b The Court Improperly Relied on Erroneous Facts In Considering the Alleged Overdose Deaths That the Defense Expert Forensic Pathologist Concluded Was Incomplete Unreliable and Inaccurate 130 B The Life Sentence Was Substantively Unreasonable 133 CONCLUSION 140 vi Case 15-1815 Document 30 01 12 2016 1682738 Page8 of 170 TABLE OF AUTHORITIES Page s Federal Cases ACLU v Clapper 785 F 3d 787 2d Cir 2015 115 117 Alvarez v Ercole 763 F 3d 223 2d Cir 2014 69 Andersen v Maryland 427 U S 463 96 S Ct 2737 49 L Ed 2d 627 1976 106 Andrews v Stegall 11 Fed Appx 394 6th Cir 2001 68 In re Application 2006 WL 1876847 N D Ind July 5 2006 123 In re Application 396 F Supp 2d 747 S D Tex 2005 122 In re Application of the U S for an Order Authorizing the Release of Historical Cell-Site Info 809 F Supp 2d 113 E D N Y 2011 117 In re Application of the United States for an Order Authorizing the Installation and Use of a Pen Register Device 497 F Supp 2d 301 D P R 2007 with In re Application of the United States for an Order for Disclosure of Telecommunications Records and Authorizing the Use of a Pen Register and Trap and Trace 405 F Supp 2d 435 S D N Y 2005 121 In re Application of the United States for an Order Authorizing the Use of a Pen Register and a Trap and Trace Device on Wireless Telephone Bearing Telephone Number Redacted Subscribed to Redacted Service by Redacted No 08 MC 0595 JO 2008 WL 5255815 E D N Y Dec 16 2008 123 In re Application of the United States for an Order Authorizing the Use of a Pen Register With Caller Identification Device Cell Site Location Authority on a Cellular Telephone 2009 WL 159187 S D N Y Jan 13 2009 122 In re Application of the United States for an Order Directing a Provider of Electronic Communication Service to Disclose Records to the Government 534 F Supp 2d 585 W D Pa 2008 121 vii Case 15-1815 Document 30 01 12 2016 1682738 Page9 of 170 In re Application of the United States for an Order for Prospective Cell Site Location Information on a Certain Cellular Telephone 460 F Supp 2d 448 S D N Y 2006 121 In re Applications of U S for Orders Authorizing Disclosure of Cell Cite Info 05-403 2005 WL 3658531 D D C Oct 26 2005 123 Authorizing Disclosure of Location-Based Servs No 07-128 2007 WL 3342243 S D Tex Nov 7 2007 124 In re Authorizing the Use of a Pen Register 384 F Supp 2d 562 on reconsideration sub nom In re Application of the U S for an Order 1 Authorizing the Use of a Pen Register a Trap Trace Device 396 F Supp 2d 294 E D N Y 2005 124 Bowen v Maynard 799 F 2d 593 10th Cir 70 Bowen v Maynard 799 F 3d 593 10th Cir 1986 67 Boyette v LeFevre 246 F 3d 76 2d Cir 2001 66 Brady v Maryland 373 U S 83 963 passim Chambers v Mississippi 410 U S 284 1973 passim Chapman v California 386 U S 18 1967 77 Cone v Bell 556 U S 449 2009 51 54 62 Cotto v Herbert 331 F 3d 217 2d Cir 2003 69 71 Crane v Kentucky 476 U S 683 1986 83 Dennis v United States 384 U S 855 1966 38 56 DiBenedetto v Hall 272 F 3d 1 1st Cir 2001 67 Douglas Oil Co Of California v Petrol Stops Northwest 441 U S 211 1979 56 Florida v Jardines __ U S __ 133 S Ct 1409 2013 120 Gardner v Florida 430 U S 349 1977 plurality opinion 129 viii Case 15-1815 Document 30 01 12 2016 1682738 Page10 of 170 Hein v Cuprum S A De C V 53 Fed Appx 134 2d Cir 2002 84 Horton v California 496 U S 128 1990 102 Klayman v Obama 957 F Supp 2d 1 D D C 2013 vacated and remanded on other grounds 800 F 3d 559 D C Cir 2015 115 Koon v United States 518 U S 81 1996 77 Kyles v Whitley 514 U S 419 1995 passim Kyllo v United States 533 U S 27 2001 119 120 Lambert v Beard 537 Fed Appx 78 3d Cir 2013 after remand by Wetzel v Lambert __ U S __ 132 S Ct 1195 2012 52 62 Leka v Portuondo 257 F 3d 89 2d Cir 2001 58 61 Limone v United States 497 F Supp 2d 43 D Mass 2007 73 Martindell v Int'l Tel Tel Corp 594 F 2d 291 2d Cir 1979 38 Mendez v Artuz 303 F 3d 411 2d Cir 2002 67 Mitchell v United States 526 U S 314 1999 94 Moore v Illinois 408 U S 786 1972 51 Muncie Aviation Corporation v Party Doll Fleet Inc 519 F 2d 1178 5th Cir 1975 73 In re Order Authorizing Prospective and Continuous Release of Cell Site Location Records 31 F Supp 3d 889 S D Tex 2014 121 Parsons v Honeywell Incorporated 929 F 2d 901 2d Cir 1991 73 People of Territory of Guam v Ignacio 10 F 3d 608 9th Cir 1993 68 In the Matter of the Search of Information Associated with Redacted @mac comthat is Stored at Premises Controlled by Apple Inc 13 F Supp 3d 157 D D C August 8 2014 107 Sherwin-Williams Co v New York State Teamsters Conference Pension and Retirement Fund 969 F Supp 465 N D Oh 1997 132 ix Case 15-1815 Document 30 01 12 2016 1682738 Page11 of 170 Smith v Maryland 442 U S 735 1979 passim Steinberg v Obstetrics-Gynecological Fertility Group P C 260 F Supp 2d 492 D Conn 2003 73 St Germain v United States Nos 03 cv 8006 CM 99 cr 339 CM 2004 WL 1171403 at 18 S D N Y May 11 2004 58 In re U S For an Order Authorizing the Disclosure of Prospective Cell Site Info 412 F Supp 2d 947 E D Wisc 2006 aff'd 06MISC-004 2006 WL 2871743 E D Wis Oct 6 2006 124 In re U S for an Order Authorizing the Use of a Pen Register and Trap on xxx Internet Service Account User Name xxxxxxx@xxx com 396 F Supp 2d 45 D Mass 2005 114 United States v Abrams 615 F 3d 541 1st Cir 1980 105 United States v Agurs 427 U S 97 1976 54 83 United States v Al-Moayad 545 F 3d 139 2d Cir 2008 97 United States v Aldeen 792 F 3d 247 2d Cir 2015 134 United States v Bailey 581 F 2d 341 3d Cir 1978 73 United States v Blake 107 F 3d 651 8th Cir 1997 1 2 71 United States v Breit 767 F 2d 1084 4th Cir 1985 59 United States v Bridges No CR 15-319 RS N D Cal 23 United States v Camacho 163 F Supp 2d 287 S D N Y 2001 93 United States v Cavera 550 F 3d 180 2d Cir 2008 en banc 126 United States v Certified Environmental Services Inc 753 F 3d 72 2d Cir 2014 passim United States v Chan 184 F Supp 2d 337 S D N Y 2002 92 United States v Chavez 549 F 3d 119 2d Cir 2008 84 x Case 15-1815 Document 30 01 12 2016 1682738 Page12 of 170 United States v Comprehensive Drug Testing Inc 621 F 3d 1162 9th Cir 2010 en banc per curiam 105 United States v Coppa 267 F 3d 132 2d Cir 2001 passim United States v Crowley 318 F 3d 401 2d Cir 2003 cert denied 540 U S 894 2003 76 United States v Davis 785 F 3d 498 11th Cir 2015 en banc 117 United States v DeSilva 613 F 3d 352 2d Cir 2010 126 United States v Diallo 40 F 3d 31 2d Cir 1994 88 United States v Diaz 176 F 3d 52 2d Cir 1999 68 United States v Dumeisi 424 F 3d 566 7th Cir 2005 73 United States v Dwyer 539 F 2d 924 2d Cir 1976 87 United States v Fatico 458 F Supp 388 E D N Y 1978 aff'd in part rev'd in part 603 F 2d 1053 2d Cir 1979 129 United States v Figueroa 548 F 3d 222 2d Cir 2008 71 77 United States v Figueroa 647 F 3d 466 2d Cir 2011 126 United States v Forrester 512 F 3d 500 9th Cir 2007 114 United States v Fucillo 808 F 2d 173 1st Cir 1987 104 United States v Fuller 149 F Supp 2d 17 S D N Y 2001 93 United States v Galpin 720 F 3d 436 2d Cir 2013 passim United States v Ganias 755 F 3d 125 2d Cir 2014 reh'g en banc granted 791 F 3d 290 2d Cir 2015 101 102 103 United States v George 975 F 2d 72 2d Cir 1992 104 United States v Gil 297 F 3d 93 2d Cir 2002 55 56 59 United States v Graham 796 F 3d 332 4th Cir 2015 reh'g en banc granted 2015 WL 6531272 4th Cir Oct 28 2015 116 117 119 120 xi Case 15-1815 Document 30 01 12 2016 1682738 Page13 of 170 United States v Holzman 871 1496 1509 9th Cir 1989 104 United States v Hsia 24 F Supp 2d 14 D D C 1998 passim United States v Iaconetti 406 F Supp 554 E D N Y 1976 73 United States v Ingram 721 F 3d 35 2d Cir 2013 Calabresi J concurring 134 United States v Jones 132 S Ct 945 2012 Sotomayor J concurring 117 United States v Karo 468 U S 705 1984 119 United States v Kim 896 F 2d 678 2d Cir 1990 139 United States v Lee 818 F 2d 1052 2d Cir 1987 128 United States v Mahaffy 693 F 3d 113 2d Cir 2012 53 United States v Manning 56 F 3d 1188 9th Cir 1995 67 United States v Mannino 635 F 2d 110 2d Cir 1980 106 United States v Maxwell 920 F 2d 1028 D C Cir 1990 104 United States v McBride 786 F 2d 45 2d Cir 1986 87 United States v Miller 425 U S 435 1976 116 United States v Ming He 94 F 3d 782 2d Cir 1996 94 United States v Peter Nash 13 Cr 950 TPG 136 United States v Olsen 737 F 3d 625 9th Cir 2013 62 63 United States v Onumonu 967 F 2d 782 2d Cir 1992 86 87 88 United States v Otero 563 F 3d 1127 10th Cir 2009 101 United States v Payne 63 F 3d 1200 2d Cir 1995 52 United States v Pollack 534 F 2d 964 D C Cir 1976 57 United States v Prescott 920 F 2d 139 2d Cir 1990 129 xii Case 15-1815 Document 30 01 12 2016 1682738 Page14 of 170 United States v Rattoballi 452 F 3d 127 2d Cir 2006 133 United States v Rigas 583 F 3d 108 2d Cir 2009 133 United States v Rivas 377 F 3d 195 2d Cir 2004 53 United States v Roche 614 F 2d 6 1st Cir 1980 103 United States v Solomonyan 451 F Supp 2d 626 S D N Y 2006 55 United States v Stifel 594 F Supp at 154 67 71 74 United States v Thai 29 F 3d 785 2d Cir 1994 84 United States v Thomas 981 F Supp 2d 229 S D N Y 2013 passim United States v Tucker 404 U S 443 1972 129 United States v Van Brandy 726 F 2d 548 9th Cir 1984 54 United States v Vilar 2007 WL 1075041 S D N Y Apr 4 2007 104 United States v Wade 512 Fed Appx 11 2d Cir 2013 68 United States v Youngblood 379 F 2d 365 2d Cir 1967 56 United States v Zemlyansky 945 F Supp 2d 438 S D N Y 2013 108 Voss v Bergsgaard 774 F 2d 402 10th Cir 1985 108 Wade v Mantello 333 F 3d 51 2d Cir 2003 66 67 Warden v Hayden 387 U S 294 1967 107 Williamson v United States 512 U S 594 1994 95 Zerega Ave Realty Corp v Hornbeck Offshore Transp LLC 571 F 3d 206 2d Cir 2009 84 85 State Cases Commonwealth v Augustine 467 Mass 230 2014 120 State v Earls 214 N J 564 2013 120 xiii Case 15-1815 Document 30 01 12 2016 1682738 Page15 of 170 Federal Statutes 18 U S C 2 9 18 U S C 371 108 18 U S C 981 982 10 18 U S C 1028 f 10 18 U S C 1030 a 2 8 18 U S C 1030 b 10 18 U S C 1341 108 18 U S C 1956 h 8 9 10 18 U S C 1960 46 18 U S C 2703 and 3122 128 18 U S C 2703 d 128 18 U S C 3122 and 3123 129 18 U S C 3127 125 126 127 128 18 U S C 3127 3 115 18 U S C 3127 4 115 18 U S C 3231 1 18 U S C 3500 23 59 60 74 18 U S C 3742 a 1 21 U S C 812 841 a 1 and b 1 A 9 21 U S C 812 841 h and b 1 A 10 21 U S C 841 b 1 A 142 21 U S C 841 and 848 108 xiv Case 15-1815 Document 30 01 12 2016 1682738 Page16 of 170 21 U S C 846 8 10 21 U S C 848 a 10 21 U S C 853 10 28 U S C 1291 1 28 U S C 2461 10 28 U S C 2703 122 128 129 47 U S C 1002 a 127 Rules Rule 6 e Fed R Crim P 12 29 40 Rule 16 Fed R Crim P 83 87 Rule 29 Fed R Crim P 18 Rule 33 Fed R Crim P passim Rule 403 Fed R Evid 68 Rule 803 4 Fed R Evid 2 95 100 101 Rule 803 24 Fed R Evid 76 Rule 804 3 Fed R Evid 17 Rule 804 3 b Fed R Evid 96 Rule 804 b 5 Fed R Evid 76 Rule 807 Fed R Evid passim Rule 807 C Fed R Evid 96 Constitutional Provisions Fourth Amendment passim Fifth Amendment passim xv Case 15-1815 Document 30 01 12 2016 1682738 Page17 of 170 Sixth Amendment passim Other Authorities Glenn R Schmitt Hyun J Konfrst Life Sentences in the Federal System United States Sentencing Commission February 2015 134 James Cook The Biggest Drug Dealer on Silk Road Has Been Sentenced to 10 Years In Prison 137 Kathleen Ridolfi Tiffany M Joslyn and Todd H Fries Material Indifference How Courts Are Impeding Fair Disclosure In Criminal Cases 106 Orin S Kerr Searches and Seizures in a Digital World 119 Harv L Rev 531 569 2005 101 Patrick Howell O'Neill The Dark Net's Cocaine King Just Got 5 Years Behind Bars 137 Spencer Ackerman NSA Review Panel Casts Doubt On Bulk Data Collection Claims The Guardian January 14 2014 115 xvi Case 15-1815 Document 30 01 12 2016 1682738 Page18 of 170 JURISDICTIONAL STATEMENT The District Court's jurisdiction is based on 18 U S C 3231 This Court's jurisdiction is based on 28 U S C 1291 and 18 U S C 3742 a This appeal is from an Order of Judgment entered June 1 2015 by the Honorable Katherine B Forrest United States District Judge Southern District of New York following defendant-appellant Ross Ulbricht's conviction after trial on seven counts charged against him in Indictment 14 Cr 68 KBF A150 1 A timely Notice of Appeal was filed June 4 2015 A1554 Ulbricht is appealing a final order of the Court regarding his conviction and sentence A1545 STATEMENT OF THE ISSUES I Whether the Court abused its discretion in precluding Ulbricht's use at trial of evidence of an investigating agent's corruption directly related to the investigation and operation of the website the defendant allegedly operated and whether the government withheld exculpatory information regarding that corruption II Whether the Court abused its discretion in curtailing the defense's cross-examination of government witnesses with respect to the defense theories of the case 1 A refers to the Appendix filed herewith S refers to the Sealed Appendix refers to citations to the trial transcripts 1 T Case 15-1815 Document 30 01 12 2016 1682738 Page19 of 170 III Whether the Court abused its discretion in precluding the testimony of two defense experts IV Whether the Court erred in excluding a statement by an unavailable witness which qualified for admission under either Rule 803 4 Fed R Evid admission against penal interest or Rule 807 Fed R Evid residual exception V Whether the Court's evidentiary errors even if insufficient individually to warrant vacating Ulbricht's conviction constituted cumulative error VI Whether the Court erred in denying Ulbricht's motions to suppress A evidence from his laptop and social media accounts because the warrants to search those materials lacked any particularity B evidence obtained via pen register and trap and trace devices that tracked Ulbricht's internet activity and location because they were implemented without a warrant VII Whether the sentence of life imprisonment imposed upon Ulbricht was procedurally and or substantively unreasonable 2 Case 15-1815 Document 30 01 12 2016 1682738 Page20 of 170 SUMMARY OF THE ARGUMENT This Brief on Appeal is filed on behalf of defendant-appellant Ross Ulbricht who after a four-week jury trial was convicted on seven counts and subsequently sentenced to life without parole The charges alleged that Ulbricht operated a website the Silk Road on which vendors offered for sale a wide variety of merchandise including controlled substances computer hacking software and false identification documents The exclusive method of payment on the site which existed on the TOR network on the Internet and provided anonymity for those operating selling and purchasing on Silk Road was through Bitcoin an electronic payment system also providing anonymity for participants in any transaction on Silk Road This appeal presents three categories of issues 1 those that occurred at trial 2 those related to the Court's denial of Ulbricht's motions to suppress certain evidence and 3 those that occurred at sentencing As detailed below those errors correspondingly 1 constituted an abuse of discretion and denied Ulbricht his Fifth and Sixth Amendment rights to Due Process a fair trial and to present a defense 2 violated his Fourth Amendment rights to be protected against unreasonable search and seizure and 3 constituted an abuse of discretion and denial of Ulbricht's Fifth Amendment Due Process rights with respect to sentencing 3 Case 15-1815 Document 30 01 12 2016 1682738 Page21 of 170 At trial the Court's evidentiary rulings precluded a valid defense by excluding material exculpatory evidence of critical law enforcement corruption by two agents in the investigation itself unreasonably curtailing cross-examination - including post hoc excision of questions and answers from the record - as well as precluding testimony of two experts proffered by the defense and a crucial statement by a cooperating witness who did not testify but which was against the penal interest of the declarant and exculpatory for Ulbricht The defense's principal elements were that a Ulbricht was not Dread Pirate Roberts DPR the alias adopted by the operator and administrator of the Silk Road website and that as government investigators and persons directly involved with the site concluded there were multiple DPR's over the course of Silk Road's existence b that DPR framed Ulbricht who had initially conceived of and constructed the Silk Road site but had divested himself of it early on as he had informed a friend who testified as a government witness and c that vulnerabilities inherent to the internet and digital data such as fabrication and manipulation of files and metadata and hacking 4 Case 15-1815 Document 30 01 12 2016 1682738 Page22 of 170 rendered much of the evidence against Ulbricht inauthentic unattributable to him and or ultimately unreliable Yet the Court's rulings covered in POINTs I II III and IV prevented the defense from presenting salient facts to the jury with respect to each of those issues by precluding 1 evidence that a Drug Enforcement Administration Special Agent Carl M Force had engaged in corruption in his investigation of Silk Road which included his and another corrupt agent's whose misconduct was not disclosed to the defense until after trial infiltration of the internal operations of Silk Road's website and communications and financial platforms 2 evidence pointing to an alternative perpetrator Mark Karpeles whom the government was actively investigating with respect to Silk Road until Ulbricht's arrest 3 evidence that DPR was paying someone claiming to be involved in law enforcement and who after trial was confirmed to be Force for information regarding the status and progress of the government's investigation of Silk Road 4 evidence that over time there was more than one DPR 5 Case 15-1815 Document 30 01 12 2016 1682738 Page23 of 170 5 evidence that a Silk Road administrator had reason to believe that the person acting as DPR whom he had never met in September 2013 was not the DPR who had hired him earlier that year and 6 evidence that the integrity of communications and information transmitted over the internet is suspect without firsthand corroboration of the source and accuracy In a case in which that lack of integrity of digital information created and transmitted on an anonymous untraceable internet network was of paramount importance and in which the government did not produce a single witness to testify firsthand that Ulbricht authored any of the communications attributable to DPR and which was permeated by corruption of two law enforcement agents participating in the investigation the restrictions on cross-examination and preclusion of expert witnesses offered to overcome those restrictions eviscerated Ulbricht's defense and denied him a fair trial Also as set forth in POINT V even if those errors do not suffice individually to compel reversal of Ulbricht's convictions they constitute cumulative error In addition as detailed in POINT VI the Court's denial of Ulbricht's suppression motion was erroneous in two respects 1 the warrants for the search of his laptop Facebook and Gmail accounts lacked any particularity and 6 Case 15-1815 Document 30 01 12 2016 1682738 Page24 of 170 2 the pen register and trap and trace devices implemented required a warrant because they tracked Ulbricht's internet activity and location intruded into his conduct within his residence and sought prospective rather than historical information Ultimately Ulbricht was sentenced to life imprisonment In so doing as set forth in POINT VII the Court committed both procedural and substantive error The former involved attributing to Ulbricht several alleged overdose deaths based on an undefined and unprecedented legal standard and then applying that standard to rely on accusations rather than the uncontroverted report of the defense's expert forensic pathologist that did not meet even the preponderance of evidence standard The latter error involved imposing a demonstrably unreasonable sentence that shocks the conscience or at very least stirs it - the most severe available reserved for a tiny fraction of the worst offenders upon a defendant who even if guilty did not himself sell any drugs but merely created a neutral internet commercial platform that enabled others to do so Accordingly it is respectfully submitted that Ulbricht's convictions should be vacated and a new trial ordered particular evidence against him suppressed or in the alternative the matter should be remanded for re-sentencing before a different judge 7 Case 15-1815 Document 30 01 12 2016 1682738 Page25 of 170 STATEMENT OF THE CASE Ulbricht was arrested October 1 2013 in San Francisco California pursuant to a Criminal Complaint charging him with a narcotics trafficking conspiracy in violation of 21 U S C 846 a computer hacking conspiracy in violation of 18 U S C 1030 a 2 and a money laundering conspiracy in violation of 18 U S C 1956 h A48 The Superseding Indictment charged Ulbricht with devising and operating Silk Road an underground website allegedly designed to enable users across the world to buy and sell illegal drugs and other illicit goods and services anonymously and outside the reach of law enforcement A150 Ulbricht is alleged to have owned and operated the site with the assistance of various paid employees who he managed and supervised from in or about January 2011 through in or about October 2013 when Silk Road was shut down by law enforcement A150-51 According to the Indictment during the period that the Silk Road website was operational it emerged as the most sophisticated and extensive criminal marketplace on the Internet and was used by several thousand drug dealers and unlawful vendors to distribute hundreds of kilograms of illegal drugs and other illicit goods and services to well over a hundred thousand buyers worldwide Id 8 Case 15-1815 Document 30 01 12 2016 1682738 Page26 of 170 The website is also alleged to have been used to launder hundreds of millions of dollars from these illegal transactions Id The Indictment further alleges Ulbricht reaped commissions worth tens of millions of dollars from the sales conducted on the website and he solicit ed the murder-for-hire of several individuals he believed posed a threat to Silk Road in order to protect his criminal enterprise and the illegal proceeds it generated A151 A The Charges Ulbricht was initially indicted February 4 2014 A87 and a Superseding Indictment was returned August 21 2014 A150 The Superseding Indictment charged Ulbricht with Distribution and Possession with Intent to Distribute Controlled Substances and Aiding and Abetting such Distribution and Possession with Intent to Distribute in violation of 21 U S C 812 841 a 1 and b 1 A and 18 U S C 2 Count One Distribution of Narcotics By Means of the Internet and Aiding and Abetting Such Activity in violation of 21 U S C 812 841 h and b 1 A Count Two Conspiracy to Distribute and Possess with Intent to Distribute Controlled Substances in violation of 21 U S C 846 Count Three Continuing Criminal Enterprise in violation of 21 U S C 848 a Count Four Conspiracy to Commit and Aid and Abet Computer Hacking in violation of 18 U S C 1030 b Count Five Conspiracy to Traffic and to Aid and Abet Trafficking in Fraudulent Identification Documents in violation of 18 U S C 9 Case 15-1815 Document 30 01 12 2016 1682738 Page27 of 170 1028 f Count Six and a Money Laundering Conspiracy in violation of 18 U S C 1956 h Id The Superseding Indictment also included forfeiture allegations pursuant to 18 U S C 981 982 21 U S C 853 and 28 U S C 2461 A163-65 Ulbricht pleaded not guilty to the charges B Pretrial Motions Ulbricht filed pretrial motions March 28 2014 seeking dismissal of all charges See Docket #21 The Court issued an Order July 9 2014 denying those motions in their entirety A99 Ulbricht filed additional pretrial motions August 1 2014 to suppress certain evidence for a Bill of Particulars for discovery and to strike surplusage from the Indictment The suppression motions sought inter alia to suppress evidence obtained via unlimited searches of Ulbricht's laptop and Gmail and Facebook accounts on the grounds they violated the Fourth Amendment because the warrants lacked the requisite particularity the searches were the fruit of unlawful pen register and trap and trace Orders used to obtain internet router identifying information regarding Ulbricht's laptop location and internet activity See Docket #48 The Court denied those motions by Order dated October 10 2014 A176 on the grounds that 1 the Court had no idea whether Ulbricht had an expectation 10 Case 15-1815 Document 30 01 12 2016 1682738 Page28 of 170 of privacy in his laptop and Facebook and Gmail accounts but regardless the warrants for these accounts were lawful in that they were not general warrants and were supported by probable cause and 2 the type of information sought in Pen-Trap orders 1 2 3 4 and 5 was entirely appropriate for that type of order and t he Pen-Trap Orders do not seek the content of internet communications in any directly relevant sense A201 203-04 C Disclosure of Force's Corruption During the Investigation Approximately a month prior to trial December 1 2014 the government disclosed to defense counsel a November 21 2014 letter to the Court regarding an ongoing federal grand jury investigation by the U S Attorney's Office for the Northern District of California in conjunction with the Public Integrity Section of the Criminal Division of the Department of Justice into former Drug Enforcement Administration DEA Special Agent Carl Force a matter under seal pursuant to Court Order and Rule 6 e Fed R Crim P A649 The letter disclosed that i n 2012 and 2013 SA Force was involved as an undercover agent in an investigation of Silk Road conducted by the U S Attorney's Office for the District of Maryland A649 The Court conducted a sealed hearing December 15 2014 regarding the sealed December 1 2014 disclosure to defense counsel regarding the grand jury investigation of Force and the government's application to preclude the defense 11 Case 15-1815 Document 30 01 12 2016 1682738 Page29 of 170 from disclosing the investigation of Force to any third party or using it at trial A224 Defense counsel moved for unsealing and disclosure of all information regarding the government's investigation of Force A238 Docket#114 #227-1 The government submitted a supplemental letter December 17 2014 regarding the sealed proceeding as to Force and the Court's endorsement of that letter requested defense counsel submit a list of particularized discovery requests regarding the investigation of Force to the Court by the following morning A662 Defense counsel submitted this list to the Court by letter December 18 2014 A669-72 In a December 22 2014 Sealed Memorandum and Decision the Court denied Ulbricht's motions to unseal the government's November 21 2014 letter and for discovery regarding the Force investigation A675-76 The Court also stated that in regard to defense counsel's ability to use information from the November 21 2014 letter at trial it would over the course of the trial entertain specific requests to use information from the November 21 2014 Letter on cross-examination and if during the course of the trial the Government opens the door to specific information or facts develop which render particularized disclosure of facts or documents relevant the Court will entertain a renewed application at that time A700 12 Case 15-1815 Document 30 01 12 2016 1682738 Page30 of 170 In light of the Court's December 22 2014 Opinion defense counsel submitted a letter December 30 2014 requesting an adjournment of Ulbricht's trial until after the conclusion of the investigation - by that time already eight months old - into Force's misconduct A701 The government opposed defense counsel's request and the Court denied the adjournment request that same day A704-06 D The Trial Ulbricht's trial commenced January 13 2015 in the Southern District of New York The government's theory of prosecution described ante was that Ulbricht created Silk Road and operated it throughout its existence until his arrest and did so intentionally and conspired to facilitate the sale of drugs and other illicit materials hacking software and false identification documents by vendors and purchasers using the site charging a commission for each transaction paid in bitcoin The defense theory was that while Ulbricht at the time 26 years old had devised Silk Road as a free-market economic experiment - as he told his friend government witness Richard Bates see post - he had as he informed Bates later divested himself of interest in Silk Road shortly after its inception The defense also posited that Ulbricht was not DPR who first appeared after Ulbricht left Silk Road that there were multiple persons successively acting as Dread Pirate Roberts 13 Case 15-1815 Document 30 01 12 2016 1682738 Page31 of 170 much like the character of that name in the movie The Princess Bride and that the DPR in 2013 who purchased and was leaked information about the government's investigation of Silk Road framed Ulbricht to absorb the consequences Also encompassed within the defense theory was evidence that the government's investigation of DPR and Silk Road had been flawed impairing its ability to apprehend and prosecute a specific alternative perpetrator Mark Karpeles the focus of the investigation for a considerable period of time In addition with pressure mounting toward the end of 2013 - because the government had access to Silk Road's computer servers overseas since July 2013 but permitted the site to continue operating while investigating the identity of DPR - the government seized on Ulbricht as DPR thereby letting the alternative perpetrator escape justice and leave Ulbricht as the wrongfully prosecuted culprit The government's first witness Chicago-based Homeland Security Investigations HSI Special Agent Jared Der-Yeghiayan who initiated an investigation of Silk Road based on intercepted mail packages from overseas arriving through Chicago T 76-77 During SA Der-Yeghiayan cross-examination he testified regarding an alternate perpetrator A336 Although the government did not object to this testimony at the time elicited and only did so subsequently at sidebar and even though the Court had ruled at sidebar 14 Case 15-1815 Document 30 01 12 2016 1682738 Page32 of 170 January 15 2015 that the testimony was appropriate when trial reconvened January 20 2015 the Court reversed its opinion and directed the government to identify the testimony during cross-examination that it proposed to strike A409-11 A441-43 The government submitted those strikes to defense counsel during the lunch break January 20 2015 and the Court endorsed them following the break refusing to permit defense counsel even a brief adjournment to reconstruct its cross-examination to cover the stricken pieces in an alternative fashion A334 A466-73 Following SA Der-Yeghiayan's testimony several other law enforcement agents involved in the Silk Road investigation at various stages including FBI Computer Specialist Thomas Kiernan testified regarding technical and forensic computer matters and through these witnesses the government admitted Ulbricht's laptop and items from its hard drive A492 494-95 However when defense counsel attempted to cross-examine these witnesses as to related computer issues the Court repeatedly curtailed or flatly denied the cross even stating at one point in the jury's presence y ou can put somebody else on the stand to do that thus improperly placing the burden on the defense A506 Yet when defense counsel sought to call two experts during the defense case Dr Steven Bellovin and Andreas Antonopoulos to respond to testimony 15 Case 15-1815 Document 30 01 12 2016 1682738 Page33 of 170 presented by the government's computer and forensics agents and by former FBI Special Agent Ilhwan Yum who testified as a lay witness but conducted a complex analysis - provided to the defense mid-trial only days prior to his testimony - of thousands of transactions regarding dozens of bitcoin wallets located on the Silk Road server and on Ulbricht's laptop see e g A532 the Court ultimately issued an Order Opinion February 1 2015 precluding the defense experts' testimony A362 A380 A385 The government also called Ulbricht's former friend Richard Bates who testified under a non-prosecution agreement T 1096-97 Bates testified he provided Ulbricht with programming assistance in late 2010 and 2011 including assistance with the Silk Road website T 1103 1128 Bates also testified that Ulbricht told Bates November 11 2011 that he had sold the Silk Road website T 1138-39 As part of its case the defense moved to admit a statement made to prosecutors by Andrew Jones who had been a Silk Road administrator was cooperating with the government and had been a proposed government witness until mid-trial Jones's lawyer stated Jones would invoke his Fifth Amendment right against self-incrimination if called to testify A563-65 A395 16 Case 15-1815 Document 30 01 12 2016 1682738 Page34 of 170 The statement detailed post in POINT IV supported the defense theory that there had been multiple persons acting as DPR and the identity of DPR had changed in September 2013 shortly before Ulbricht's arrest The Court however denied the defense's application to admit Jones's statement as a statement against penal interest under Rule 804 3 Fed R Evid or the residual exception in Rule 807 Fed R Evid A581-83 589 E The Charge and Verdict The government rested the afternoon of February 2 2015 and the defense moved for a judgment of acquittal on all seven counts pursuant to Rule 29 Fed R Crim P T 2023 Those motions were denied T 2029 The defense began presentation of its case the afternoon of February 2 2015 and rested the next afternoon of February 3 2015 T 2001 2126 Closing argument occurred that afternoon T 2126 The Court charged the jury the morning of February 4 2015 and the jury began deliberating February 4 2015 at 11 55 a m T 2329 The Court received a note from the jury foreperson at 3 23 p m that afternoon announcing the jury had reached a verdict T 2334 Ulbricht was found guilty on all counts T 2334-37 17 Case 15-1815 Document 30 01 12 2016 1682738 Page35 of 170 F Post-Trial Motions and Further Disclosure Regarding Corruption In the Investigation Ulbricht filed motions March 6 2015 for a new trial pursuant to Rule 33 Fed R Crim P See Docket #224 After those motions were filed on March 25 2015 seven weeks after trial concluded in this case the government filed criminal charges against Force and another participant in the Silk Road investigation former Secret Service Special Agent Shaun Bridges in the Northern District of California The government filed a letter March 30 2015 notifying the Court that the Complaint regarding the corruption investigation into these two agents both of whom had conducted illegal activity during the course of their investigation into DPR and the Silk Road website had been unsealed See Docket #226 This was the first time the defense or the Court was informed there was a second corrupt agent involved in the Silk Road investigation Ulbricht filed a Reply April 16 2015 and included motions related to the government's inadequate and untimely disclosure of the investigations of Force and Bridges See Docket #233 A722 The Court issued an Opinion and Order April 27 2015 denying Ulbricht's Rule 33 motions in their entirety A876 G Sentencing Prior to Ulbricht's sentencing in March and April 2015 the government provided defense counsel and the Probation Office with reports of six overdose 18 Case 15-1815 Document 30 01 12 2016 1682738 Page36 of 170 deaths for inclusion in the Pre-Sentence Report which the government claimed resulted from drugs sold on the Silk Road website and which it believed were relevant conduct that could be taken into account at sentencing See Pre-Sentence Report PSR 61-86 Ulbricht submitted a report from an expert forensic pathologist Dr Mark Taff contesting the government's claims that the deaths were causally related to drugs sold on Silk Road and asserting as a result the alleged overdose deaths should not have been a factor at sentencing A903 S437 Ulbricht's sentencing submission including 99 letters submitted on Ulbricht's behalf sought a sentence well below the applicable advisory Guidelines range A973 At sentencing May 29 2015 the Court ruled the overdose deaths had been properly included in the Pre-Sentence Report and were related conduct relevant to Ulbricht's conviction A1472 Ulbricht was sentenced on Counts Two and Four to a period of life imprisonment to run concurrently and on Count Five to five years' imprisonment to run concurrently on Count Six to 15 years' imprisonment also concurrent and for money laundering in Count Seven to 20 years also concurrent A1540 The Judgment against Ulbricht was filed June 1 2015 and Ulbricht filed his Notice of Appeal of his sentence and conviction June 4 2015 A1554 19 Case 15-1815 Document 30 01 12 2016 1682738 Page37 of 170 ARGUMENT POINT I THE COURT ABUSED ITS DISCRETION AND DENIED ULBRICHT HIS FIFTH AND SIXTH AMENDMENT RIGHTS TO DUE PROCESS THE RIGHT TO PRESENT A DEFENSE AND A FAIR TRIAL BY A PRECLUDING THE DEFENSE FROM USING AT TRIAL THE EVIDENCE RELATING TO DEA SPECIAL AGENT CARL FORCE'S CORRUPTION B REFUSING TO ORDER THE GOVERNMENT TO PROVIDE ADDITIONAL DISCOVERY AND BRADY MATERIAL REGARDING CORRUPTION AND C DENYING ULBRICHT'S MOTION FOR A NEW TRIAL BASED ON ADDITIONAL POST-TRIAL DISCLOSURES REGARDING FORCE AND ANOTHER CORRUPT LAW ENFORCEMENT AGENT INVOLVED IN THE SILK ROAD INVESTIGATION As set forth ante at 11-13 in December 2014 approximately one month prior to trial the government informed the defense that former DEA Special Agent Carl Force Force was under investigation - and had been formally for approximately eight months - for corrupt activity directly related to his participation in the investigation of the Silk Road and Dread Pirate Roberts DPR A650 Indeed Force as a member of the Baltimore Task Force had allegedly engaged DPR in computer chats that resulted in a murder-for-hire plot targeting a former Silk Road employee The government moved to preclude the defense's use of that information at trial based on the secrecy of the grand jury investigation of Force and because the government claimed Force's investigation of Silk Road was wholly independent of 20 Case 15-1815 Document 30 01 12 2016 1682738 Page38 of 170 the case against Ulbricht - alleged to be DPR - prosecuted in the Southern District of New York A663 The Court granted the government's application A673 The Court also denied Ulbricht's motion for discovery and subsequently to adjourn the trial until after the investigation of Force was complete A675 A706 In addition at the government's urging during trial the Court altered its pretrial ruling and denied the defense use of information and discovery that even the government in its pretrial application and the Court in deciding it had agreed could be utilized at trial As detailed below the Court abused its discretion and denied Ulbricht his Fifth and Sixth Amendment rights to Due Process a fair trial and to prepare and present a defense because the serial preclusion was based on faulty premises due in large part to the government's deliberate and calculated failure to provide either the Court or the defense salient and material facts including a contrary to the government's representations to the Court there was not any need to keep the grand jury investigation secret from its target as Force was already fully aware of it and it was nearly if not entirely complete by the time trial in this case began b Force was not the only corrupt federal law enforcement agent involved in the Silk Road investigation as a Treasury Special Agent Shaun Bridges was also under investigation for conduct in concert 21 Case 15-1815 Document 30 01 12 2016 1682738 Page39 of 170 with related to and similar to Force's and had also been interviewed and therefore cognizant of the investigation prior to December 2014 - yet the government never mentioned or alluded to Bridges at all in its pretrial disclosures c contrary to the government's claim Force's and Bridges's corruption was not independent of the SDNY prosecution Rather as demonstrated by a trove of internal law enforcement memoranda and communications produced after the Court had decided the Force issue pursuant to 18 U S C 3500 3500 material the Silk Road investigation was a coordinated interrelated interdependent effort by several federal districts ultimately directed and controlled by SDNY thereby rendering the information about Force and Bridges relevant exculpatory and material and d Force's and Bridges's misconduct was not limited to that revealed by the government pretrial but rather as established by the Criminal Complaint filed against Force and Bridges a mere seven weeks after the verdict in this case encompassed far more The extent of Force's knowledge of the investigation of him the involvement of Bridges and the broader scope of Force's and Bridges's misconduct in relation to this case as well as the trajectory of the investigation 22 Case 15-1815 Document 30 01 12 2016 1682738 Page40 of 170 were not known to the defense until after trial - indeed until after post-trial motions for new trial pursuant to Rule 33 Fed R Crim P were filed although the information was included in the Reply In fact the full nature of Force's and Bridges's misconduct has yet to be disclosed as the government quickly reached plea agreements with both resolving their cases without any additional disclosure to the public or the defense herein See United States v Bridges No CR 15-319 RS N D Cal Docket#49 #65 Thus in denying Ulbricht's post-trial Rule 33 motion based on the Force and Bridges corruption and the government's knowing failure to make full disclosure prior to trial the Court further abused its discretion As a result Ulbricht's convictions should be vacated and a new trial ordered A The Government's Eve-of-Trial Disclosure of Force's Corruption In its November 21 2014 letter to the Court subsequently provided to defense counsel December 3 2014 the government disclosed its ongoing investigation of Force A649 2 According to the government's letter the investigation had thus far revealed that Force used his position as a DEA agent for self-gain by leaking investigative information to the operator of Silk Road in 2 The government's letter along with a series of other correspondence and exhibits related to the issue was not unsealed until the government formally charged Force and Bridges seven weeks after trial in this case See Docket#226 23 Case 15-1815 Document 30 01 12 2016 1682738 Page41 of 170 exchange for payment and hijacking a cooperating witness's Silk Road account to obtain $350 000 in Bitcoins In its November 21 2014 letter the government informed the Court that Force is the undercover agent whom Ulbricht allegedly hired to arrange the murder-for-hire as described in that indictment and that Force is now being investigated by USAO-San Francisco for among other things leaking information about USAO-Baltimore's investigation to Ulbricht in exchange for payment and otherwise corruptly obtaining proceeds from the Silk Road website and converting them to his personal use A649 The government's letter added that USAO San Francisco first began investigation into SA Force in the Spring of 2014 A650 Yet the information about the investigation was not disclosed to the defense in this case until December 3 2014 essentially one month prior to trial The government also claimed that it does not believe that the ongoing investigation of SA Force is in any way exculpatory as to Ulbricht or otherwise material to his defense but disclosed the information in an abundance of caution A649 Furthermore while the government asserted that Force played no role in SDNY's investigation of Silk Road the government admitted that SDNY has been assisting USAO-San Francisco with its investigation by sharing relevant evidence collected from this Office's investigation of Silk Road including 24 Case 15-1815 Document 30 01 12 2016 1682738 Page42 of 170 evidence from the server used to host the Silk Road website the 'Silk Road Server' and evidence from Ulbricht's laptop computer A649-50 In response the defense submitted in addition to sealed submissions at S434 A669 two sealed ex parte letters setting forth the defense theories and the relationship of Force's misconduct to them and to various items produced in discovery including some not referred to by the government in its November 21 2014 letter 3 The defense moved to unseal the government's November 21 2014 letter so the defense could perform a complete investigation and to use at trial At a sealed December 15 2014 pretrial conference the government claimed that the grand jury investigation of Force was active not complete and in some respects was still in its early steps A227 Also the government contended it did not know the full extent of Force's misconduct but continued to connect the dots - which it had been doing for almost eight months and continued to do while keeping the defense in the dark A252 Yet the government sought to preclude the defense from launching any inquiry designed to find out the full extent of Force's misconduct in relation to the Silk Road investigation As the Court remarked during the December 15 2014 3 Those ex parte letters have not been unsealed or provided to the government because inter alia Ulbricht still faces charges in the District of Maryland See Docket#281 #283 Of course those letters can be made available to the Court upon request 25 Case 15-1815 Document 30 01 12 2016 1682738 Page43 of 170 pretrial conference the government's disclosure was functionally the same as no disclosure at all since the defense could not use it A248 - and even that was just a small fraction of what the government knew about Force's and Bridges's misconduct Also regarding the need for continued secrecy of the investigation the government in a December 12 2014 letter to the Court maintained that Force is aware that he is under investigation insofar as he has been interviewed in connection with the grand jury investigation He is not however aware of the full range of the misconduct for which he is being investigated A659 Docket #227-1 at 68 prosecutors believe that disclosure of materials taken from the case file would threaten to reveal the full scope of the investigation and might cause Force as well as other potential subjects co-conspirators or aiders and abettors to flee destroy evidence conceal proceeds of misconduct and criminal activity or intimidate witnesses Ulbricht also submitted a detailed discovery request demanding additional disclosure with respect to Force's misconduct A669 The Court directed the defense to prioritize its requests A672 which the defense did The Court then denied all of the defense's discovery requests and granted the government's application to preclude the defense from investigating Force's misconduct or exploring it at trial A673 In so doing the Court held that 26 Case 15-1815 Document 30 01 12 2016 1682738 Page44 of 170 Ulbricht had not demonstrated a particularized need sufficient to outweigh the need for continued secrecy of the grand jury investigation A687 691-96 The Court added that to the extent there is any information revealed or developed during the Force Investigation that is material and potentially exculpatory the Government must disclose such information to the defense A699 In response Ulbricht moved for adjournment of the trial until the government had completed its grand jury investigation of Force and the full nature of his alleged misconduct was known and available to Ulbricht's defense A701 4 The Court denied that motion as well A706 B The Court's Further Preclusion at Trial of Evidence the Pretrial Rulings Had Permitted the Defense to Use During the December 15 2014 pretrial conference the Assistant United States Attorney when asked by the Court to define the parameters of the prohibition imposed on the defense by Rule 6 e Fed R Crim P answered What they can't reveal is that Force is under a grand jury investigation It's just a matter that he's being investigated for certain activities A249 The AUSA added that s o in terms of what Rule 6 e prohibits we think it prohibits them eliciting somehow that he's under a grand jury investigation That's the basic point I mean that's 4 In its opinion precluding evidence of Force's misconduct the Court acknowledged that it is clear that precisely what Force did or did not do remains unknown A675 27 Case 15-1815 Document 30 01 12 2016 1682738 Page45 of 170 what 6 e requires be kept secret while the investigation is pending They still have many facts in their possession They've had them in their possession long ago Id See also A253 all that is evidence that has been produced in discovery and they are free to use it the same way that they would use other evidence 5 At trial however the government successfully moved to expand the proscription to include those very facts thereby preventing the defense from using documents and information in cross-examination or from introducing them as part of the defense case For example the government successfully prevented the defense from cross-examining witnesses with respect to the electronic communications between DPR and Silk Road user DeathFromAbove who represented himself to be a person with inside information about federal law enforcement's investigation of Silk Road which he was offering to sell to DPR 5 During the December 15 2014 pretrial conference the Court commented on the government's inconsistent and expansive position with respect to the scope of the Rule 6 e proscription it sought In response to the AUSA's remark that the point is we're not trying to say certain witnesses certain evidence is off limits It's the fact that this is a grand jury investigation That's what they're prohibited from disclosing the Court replied w ell I hear what you're saying And it's like ships passing in the night Because on the one hand it's the content of the investigation And what you're suggesting is it's really not the content it's the fact of A 252-53 emphasis added 28 Case 15-1815 Document 30 01 12 2016 1682738 Page46 of 170 A575 Some of those communications had been included in the government's initial Exhibit list circulated a month prior to trial Shortly before the government rested it revealed in a February 1 2015 letter that it appears that DeathFromAbove was controlled by former Special Agent Force based on information that was recently obtained from USAO-San Francisco regarding their ongoing grand jury investigation into Force Following the defendant's first attempt to seek to use Defense Exhibit E containing communications between DPR and DeathFromAbove with Special Agent DerYeghiayan the Government consulted with the lead Assistant U S Attorney handling the Force investigation who provided evidence that Force controlled the DeathFromAbove account and sent the messages to Dread Pirate Roberts A710 Yet the government in its earlier submissions and in prior sidebars had never identified the DeathFromAbove username account as being controlled by Force and therefore its use at trial was not precluded by the Court's pretrial ruling The government's letter demonstrates that during trial it used the cross-examination of Homeland Security Investigations Special Agent Jared Der-Yeghiayan to continue its investigation of Force and to generate further Brady material but without disclosing it to the defense until the eve of the defense case itself Rather as discussed post at 49 the government successfully albeit impermissibly shoehorned that information into the Court's pretrial restrictions on 29 Case 15-1815 Document 30 01 12 2016 1682738 Page47 of 170 the defense's ability to explore what had been provided in discovery and even included in the government's initial Exhibit List A575 Thus at trial the government and Court foreclosed an entire additional category of information vital to the defense that the pretrial ruling had left available to Ulbricht That compounded the initial abuse of discretion manifested in the preclusion of the Force misconduct generally and constituted a separate abuse of discretion that effectively ambushed the defense 1 The Post-Trial Revelation of Bridges's Corruption and the Additional Post-Trial Disclosures of Force's Misconduct Just seven weeks after trial concluded in this case following Ulbricht's filing of his initial papers in support of his Rule 33 motion the government formally charged both Force and Bridges in a Criminal Complaint the Force Bridges Complaint in the Northern District of California That Complaint also revealed information that was not previously disclosed by the government Obviously the most dramatic aspect was the involvement of a second federal law enforcement agent SA Bridges in the corrupting of the Silk Road investigation However there were other revelations that appeared for the first time in the Force Complaint but which should have been disclosed to Ulbricht's counsel earlier and even before trial 30 Case 15-1815 Document 30 01 12 2016 1682738 Page48 of 170 The Force Bridges Complaint was unsealed March 30 2015 while the verdict herein was returned February 4 2015 A Department of Justice Press Release March 30 2015 Former Federal Agents Charged With Bitcoin Money Laundering and Wire Fraud available at http www justice gov opa pr former-federal-agents-charged-bitcoin-moneylaundering-and-wire-fraud summarized the Force Bridge's Complaint's allegations against Force as follows Force used fake online personas and engaged in complex Bitcoin transactions to steal from the government and the targets of the investigation Specifically Force allegedly solicited and received digital currency as part of the investigation but failed to report his receipt of the funds and instead transferred the currency to his personal account In one such transaction Force allegedly sold information about the government's investigation to the target of the investigation As the Force Bridges Complaint itself notes i n late January 2013 members of the Baltimore Silk Road Task Force to include BRIDGES and FORCE gained access to a Silk Road administrator account as a result of the arrest of a former Silk Road employee S453 According to the Force Bridge's Complaint Force created certain fictitious personas S451 and used those phony personas to seek monetary payment offering in exchange not to provide the government certain information Id Force also created fictional characters such as Kevin a supposed law 31 Case 15-1815 Document 30 01 12 2016 1682738 Page49 of 170 enforcement insider who was providing information to Nob who was Force in his authorized undercover role masquerading as a drug dealer which Nob in turn was corruptly providing to DPR S462 Also Force stole and converted to his own personal use a sizable amount of bitcoins that DPR sent to Force S452 Bridges also illegally acquired Bitcoin from the Silk Road website through an account law enforcement believed Bridges controlled and or had access with others to and which appears to have initiated sizeable bitcoin thefts and assisted Force in his illegal endeavors S489-97 In describing Force's assumption of the screen name DeathFromAbove discussed ante at 30 which Force used alternately in an attempt to extort DPR and or to provide inside law enforcement information to DPR the Force Bridge's Complaint concludes that Force was the source of certain information in the LE_counterintel file found on Ulbricht's laptop because the excerpts in that file contain information that came from a person or persons inside law enforcement in part because of their substance and in part because of their use of certain terminology and acronyms that are not widely known by the public S460 As a result in assessing Force's activities as DeathFromAbove the Force Complaint posits that such misconduct demonstrates that FORCE had a history of 1 creating fictitious personas that he did not memorialize in his official 32 Case 15-1815 Document 30 01 12 2016 1682738 Page50 of 170 reports or apprise his superiors at the DEA or the prosecutor of 2 soliciting payments from DPR 3 providing law-enforcement sensitive information to outside individuals when the disclosure of such information was not authorized and not memorialized in any official report S474 The Force Bridges Complaint also erased any doubt that the investigation of Force and Bridges was already fully known to them when in December 2014 the government cited secrecy in precluding Ulbricht from using the information at his trial For example Force resigned from the DEA May 4 2014 shortly after law enforcement began the current investigation S455 483 Days later May 8 2014 Force wired $235 000 to an offshore account in Panama with the Force Bridge's Complaint noting that he did so presumably after learning of the government's investigation and after he had resigned S487 In fact Force even voluntarily submitted to an interview by law enforcement that his lawyer suggested S488 That meeting occurred May 30 2014 id a full six months before the defense herein was notified of Force's misconduct Similarly Bridges was interviewed with counsel by law enforcement more than once including November 13 2014 eight days before the government wrote the Court in this case seeking to preclude the defense's use of such information ostensibly in order to preserve its secrecy S495-96 33 Case 15-1815 Document 30 01 12 2016 1682738 Page51 of 170 Thus the investigation of Bridges too was already fully underway by Fall 2014 and his misconduct was known by then as well as demonstrated by the contents of the interviews of him Bridges's relevance to this case is beyond obvious as the Force Bridge's Complaint attests Bridges had been assigned to the Secret Service's Electronic Crimes Task Force S488 Also Bridges's specialty was in computer forensics and anonymity software derived from TOR Id Bridges was also the Task Force's subject matter expert in Bitcoin Id Both elements were distinctive features of Silk Road and the subject of extensive testimony by government witnesses at trial Beyond Bridge's particular expertise firmly in the wheelhouse of multiple critical aspects of this case computer forensics TOR and Bitcoin Bridges placed himself firmly in the middle of important factual issues such as his serving as the affiant for the seizure of Mark Karpeles's accounts at a Bitcoin exchange firm Dwolla in May 2013 S489 6 As set forth ante he also controlled an account that initiated sizeable bitcoin thefts from the Silk Road website S491 In addition Bridges clearly worked in concert with Force S491 493 Thus Force was assisted in his illegal unauthorized infiltration and manipulation of the Silk Road website by a computer forensics agent with expertise in 6 Karpeles's relevance to this case as well as to Force's misconduct is detailed post at 65 POINT II 34 Case 15-1815 Document 30 01 12 2016 1682738 Page52 of 170 anonymity and Bitcoin Yet none of this information of the site's contamination was disclosed to the defense herein until the filing of the Force Bridges Complaint Force's deposits totaled at least approximately $757 000 for the roughly year long period beginning April 2013 through May 2014 S455-56 footnote omitted Nor does that include other deposits made afterward S456 Any deposits made in the first half of 2014 would of course have occurred after Ulbricht had been arrested October 1 2013 begging the question of the source of those funds The Force Bridges Complaint also divulged additional misconduct by Force shedding light on his capacity for fraud deception forgery abuse of his government authority and access - including predatory and retaliatory conduct and false accusations against innocent persons - and inventing complex layered cover stories to conceal his misdeeds For instance the Force Bridges Complaint S477-78 in a section entitled FORCE's Unlawful Seizure of R P 's Funds details Force's series of attempts to convert the contents of an account held by R P which efforts included abuse of various criminal law enforcement privileges and false accusations against R P to justify seizure of the account Force also misused subpoenas and in effect committed forgery by using his supervisor's stamp S477 481-83 S452 Force used his supervisor's signature 35 Case 15-1815 Document 30 01 12 2016 1682738 Page53 of 170 stamp without authorization on an official U S Department of Justice subpoena and sent the subpoena to a payments company Venmo directing the company to unfreeze his own personal account He also improperly performed queries in law enforcement criminal databases S475 Moreover Force 'papered up' the seizure of the digital currency portion of one of his victim's accounts in such a way that he may have thought he would be covered in the event anyone ever asked any questions about his conduct S480 S481 Force's documentation was an attempt to give himself plausible deniability by memorializing the digital currency seizure The detail in the Force Bridges Complaint was of course tellingly absent from the government's description of Force's corruption in its November 21 2014 letter in this case as was any mention of Bridges or their knowledge of the investigation s A649 Thus to a significant degree the extent and in some respects the nature of Force's misconduct - as well as Bridges's participation altogether - was hidden by the government from the defense and the Court in this case until after trial 36 Case 15-1815 Document 30 01 12 2016 1682738 Page54 of 170 C The Court Abused Its Discretion In Precluding Ulbricht from Utilizing at Trial Information Related to Force's Corruption As detailed below the Court abused its discretion in five separate respects with respect to its preclusion of the information and documents related to Force's corruption 1 in refusing to permit Ulbricht to use the information and documents at trial or even to investigate them further 2 in denying Ulbricht's discovery demands with respect to Force which would have compelled the government to disclose additional information about Force's corruption - and that of Bridges altogether - that was not revealed until after trial 3 in denying Ulbricht's request for adjournment of the trial until after the grand jury investigation of Force - at that point underway for more than eight months already - was complete 4 in expanding its ruling at trial by prohibiting use of evidence that the Court's pretrial ruling had expressly permitted Ulbricht to present and 5 in denying Ulbricht's post-trial Rule 33 motion based on the post-trial disclosures of details of Force's and Bridges's misconduct 37 Case 15-1815 Document 30 01 12 2016 1682738 Page55 of 170 In many respects the Court's error was in large part the consequence of the government's purposeful failure in its extraordinarily circumscribed pretrial account to disclose material information about Force's corruption and about Bridges's corruption at all until after trial Contrary to the government's claims and the Court's decision the evidence of Force's and Bridges's corruption was both material and exculpatory Moreover the Due Process right to Brady material Brady v Maryland 373 U S 83 963 requires that it be used effectively a principle that certainly establishes a compelling and particularized need to modify any protective order including any issued pursuant to Rule 6 e Fed R Crim P to permit a defense investigation as well as use of admissible evidence at trial See e g Martindell v Int'l Tel Tel Corp 594 F 2d 291 296 2d Cir 1979 see also Dennis v United States 384 U S 855 868 1966 Indeed the government claimed it could not discern any exculpatory character in the information it provided in its November 21 2014 letter but disclosed the Force investigation in an abundance of caution This of course begs the question abundance of caution with respect to what The answer is obvious with respect to the government's constitutional obligation to disclose exculpatory evidence Transparently the government's nomenclature simply 38 Case 15-1815 Document 30 01 12 2016 1682738 Page56 of 170 sought to avoid denominating the obvious that the Force disclosures constituted exculpatory information 1 There Was Not Sufficient Need to Maintain Secrecy of the Investigation of Force and Bridges to Ulbricht's Detriment In This Case As a threshold matter the Force Bridges Complaint reveals that the government's pretrial application in this case to keep secret the investigation of Force or even Bridges the investigation of whom the government concealed altogether in this case and the information derived therein was without foundation While the government acknowledged pretrial that Force had been interviewed it did not disclose there were two interviews or as evident from the Force Bridges Complaint that those interviews provided Force extensive knowledge about the investigation S 478-81 483-88 Also by the time of trial in this case the grand jury presentation regarding Force had already occurred A660 and the charges were imminent as demonstrated by their issuance only seven weeks after the verdict in this case In addition the government inexcusably waited eight months before informing the defense of the misconduct by Force - and never did prior to trial with respect to Bridges As the Complaint notes the government opened its investigation of Force May 2 2014 S495 Two days later DoJ's Public Integrity Section opened an official investigation of him Id 39 Case 15-1815 Document 30 01 12 2016 1682738 Page57 of 170 Nor were there any facts in the Force Bridges Complaint that were not entirely established well before the government notified the defense in this case much less before trial herein The last misconduct by either Force or Bridges allegedly occurred in mid-2014 2 The Record Demonstrates That Silk Road Investigations Were Coordinated and Combined The government's repeated insistence that the SDNY's investigation was independent of that in which Force and Bridges were involved is demonstrably repudiated by the record created by the government's investigators and prosecutors themselves That record establishes that all of the federal investigations of Silk Road were coordinated and for practical purposes and for determining relevance to this case combined By any conception of independence these investigations do not qualify Rather they were decidedly interdependent because the agents conducting the investigation were in continued contact with each other regarding the status of the investigation supervisory law enforcement officials coordinated the investigations each investigation made its fruits available to the other and used that information from the companion investigation s 40 Case 15-1815 Document 30 01 12 2016 1682738 Page58 of 170 information was entered in law enforcement databases to which all federal law enforcement enjoyed access the investigations sought information about and from the same targets at the same time and ultimately SDNY was able to dictate the distribution of federal charges in the case for all of the districts involved in the coordinated investigations The 3500 material produced for SA Der-Yeghiayan serves as a catalogue of the interaction and linkage of the various investigations of the Silk Road website For example a report by SA Der-Yeghiayan regarding his investigation notes that in October 2012 HSI Baltimore office provided SA Der-Yeghiayan with a file containing all of the Undercover UC chats made between a UC agent and DPR A828 Those were Force's chats with DPR Similarly in a May 22 2013 e-mail to Lisa M Noel an HSI intelligence analyst with HSI Baltimore and part of that Silk Road Task Force SA Der-Yeghiayan wrote that w e would like to examine some of the language usage diction etc with the new U C chats from Nob A747 Again Nob was Force Thus at the outset of his investigation - which the government cannot claim was independent of the case against Ulbricht - SA Der-Yeghiayan was provided 41 Case 15-1815 Document 30 01 12 2016 1682738 Page59 of 170 with the principal product of the Baltimore investigation generated by Force himself Nor was there any attenuation of that direct connection nor did the government even attempt to establish any Other e-mails and reports authored by SA Der-Yeghiayan describe the continued contacts between Baltimore and Chicago which evolved into the SDNY investigation and prosecution In a May 15 2013 e-mail SA Der-Yeghiayan wrote that i n early August 2012 HSI Chicago notified HSI Baltimore of the connection made between Mark Karpeles and Silk Road and stated that Karpeles was a target of HSI Chicago's investigation A748 Also HSI Baltimore was provided a copy of the HSI Chicago's ROI Report of Investigation that highlighted all the facts of the connection Id In that same e-mail SA Der-Yeghiayan memorialized the following interaction HSI Chicago contacted HSI Baltimore and they confirmed that they shared all of HSI Chicago's information on KARPELES with members of their task force HSI Chicago discovered that their IRS Agent DEA Agent and SS Agent all inputted KARPELES into their individual investigations as a target and a potential administrator of the Silk Road based on HSI Chicago's ROI information Id Subsequently in an undated report A843 SA Der-Yeghiayan provided a lengthy chronology detailing the continued intersection of the Silk Road 42 Case 15-1815 Document 30 01 12 2016 1682738 Page60 of 170 investigations throughout 2013 and which was digested in Ulbricht's Rule 33 Reply at A748-56 Another seven-page report from SA Der-Yeghiayan regarding various investigations into Silk Road further recounts their interlocking character also digested in Ulbricht's Rule 33 motion A846 Among the entries in SA Der-Yeghiayan chronology were the following HSI Chicago and HSI Baltimore conducted another conference call July 9 2013 about the Silk Road investigation A852 During that call neither the HSI Baltimore agents nor the D Md AUSA on the call mentioned - despite a question from SA Der-Yeghiayan whether there were any new developments - that another D Md AUSA had scheduled a meeting with Karpeles's attorneys Id That meeting occurred July 11 2013 Id During the meeting Karpeles's attorney randomly brought up the Silk Road and stated that their client was willing to tell them who Karpeles suspects is currently running the website in order to relieve their client of any potential charges for 18 U S C 1960 Id Also the D Md AUSA proceeds to set up a meeting with Karpeles overseas Id HSI Chicago did not learn of the July 11 2013 meeting with Karpeles's attorneys until July 16 2013 Id Subsequently one of the D Md AUSA's informed SA Der-Yeghiayan that the other D Md AUSA continued to negotiate 43 Case 15-1815 Document 30 01 12 2016 1682738 Page61 of 170 with Karpeles's attorneys - despite SA Der-Yeghiayan's objections - and has changed the meeting location to Guam later on in August Id July 12 2013 there was a coordination meeting with HSI Chicago HSI Baltimore FBI New York and multiple DoJ Department of Justice attorneys and CCSIP attorneys S852 At that coordination meeting HSI Chicago mentioned Karpeles as their main target Id A month later in August 2013 SA Der-Yeghiayan swore to an affidavit composed by the SDNY AUSA in support of the SDNY search warrant application for Karpeles's e-mail accounts Again in light of this overwhelming evidence any claim of independence is contradicted by the government's own documents and is therefore untenable 7 Nor was Force's investigation into Silk Road transitory or superficial in any respect It began in February 2012 S470 and generated dozens of DEA-6 reports of his authorized undercover activities investigating the Silk Road website and which were produced as discovery herein 7 A separate question the defense asked and which still merits an answer is whether any evidence related to Nob or Flush both accounts controlled by Force was introduced in the grand jury that indicted Ulbricht 44 Case 15-1815 Document 30 01 12 2016 1682738 Page62 of 170 In fact as the Force Bridges Complaint points out information-sharing and its impact relevant to this case continued through the summer of 2013 by late July 2013 the Baltimore Silk Road Task Force had been made aware that the FBI was seeking to obtain an image of the Silk Road server and therefore FORCE may have had reason to fear that any communications between himself and DPR would be accessible to the FBI in the event the FBI was successful in imaging the server S465-66 8 Even the government contradicts its naked claim of independence In explaining its realization after the defense attempted to introduce certain documents provided in discovery that DeathFromAbove was among Force's aliases see ante at 30 the government states in its response to Ulbricht's Rule 33 Motion that former SA Force had access to law enforcement reports filed by SA Der-Yeghiayan including reports concerning his suspicions regarding Anand Athavale which was likely the source of the information leaked by Force through 8 That would also ostensibly have provided DPR via Force as Nob or French Maid or DeathFromAbove or perhaps some other incarnation of his and or Bridges's with advance notice of the FBI's imaging of Silk Road's servers - consistent with the defense's position that DPR purchased and or was provided with information that permitted him to formulate and implement - with Force's and perhaps Bridges's assistance - an escape plan that also incriminated Ulbricht falsely In that context Force also learned at least days in advance that law enforcement intended to make an arrest of DPR in late September 2013 thereby giving him ample time to warn DPR S466 Yet Ulbricht did not assume any additional security protocols but instead violated even the most fundamental security precepts in multiple ways 45 Case 15-1815 Document 30 01 12 2016 1682738 Page63 of 170 the 'DeathFromAbove' account Response to Rule 33 Motion at 14 n 4 Dkt#230 Ultimately the investigations were not only interrelated and interdependent but their outcomes were dictated by SDNY as SA Der-Yeghiayan reported in a September 20 2013 e-mail to an HSI colleague A854 Thus in light of all of the evidence set forth above the interdependence and continuing relationship among the investigations including that in which Force and Bridges participated is indisputable 3 The Information Regarding the Investigation of Force and Bridges Is Relevant to This Case Regardless Whether the Investigations Were Independent Even assuming arguendo the SDNY investigation was independent from the District of Maryland investigation the information and material regarding Force and Bridges was as evidenced by the government's own strategy in preparing for trial herein as well as other objective indicia plainly relevant to this case a The Government's Initial Exhibit List The government's initial Exhibit List was provided December 3 2014 - two days after the government's November 21 2014 letter to the Court setting forth information regarding the investigation of Force was disclosed to the defense It contained at least 14 Government Exhibits directly relevant to Force including in 46 Case 15-1815 Document 30 01 12 2016 1682738 Page64 of 170 his undercover capacity as nob and or his unauthorized Silk Road user name french maid and or to the account assigned to the user name Flush Those Exhibits included GX 220 GX 225 GX 227 GX 229A GX 229B GX 241 GX 243 GX 250 GX 252 GX 275 GX 127D GX 223 GX 240B GX 242 A434 The government's transparently tactical removal of those proposed Exhibits from its presentation at trial does not eliminate their relevance but merely reflects the government's recognition that they undermined the government's claim that Force's corruption was unrelated to the charges against Ulbricht and his defenses thereto Also earlier as part of discovery the government had produced Force's DEA-6 reports which further demonstrates the government's belief - prior to discovering his misconduct - that Force's investigative activities were relevant and connected to the SDNY prosecution b The Importance of the First Half of 2013 Regarding the Evidence At Trial The relevance of the misconduct committed by Force and Bridges is also apparent from the time frame in which it is believed to have commenced and occurred - the first half of 2013 That period was critical in the context of the creation and collection of evidence used against Ulbricht at trial and the defense's response to it 47 Case 15-1815 Document 30 01 12 2016 1682738 Page65 of 170 A partial timeline of relevant events during that span - described only by information possessed by the defense at the time of trial and not including reference to Force or Bridges misconduct is set forth in Ulbricht's Rule 33 Reply A722 D The Court Abused Its Discretion By Deviating From Its Pretrial Ruling and Precluding Evidence That It Had Determined Would Be Admissible In foreclosing the defense's use of any information or materials relating to Force and his misconduct the government exceeded the boundaries set by the Court in its pretrial rulings on the issue and the Court permitted the government to do so While the embargo was supposed to cover only the information and materials generated as part of the ongoing grand jury investigation of Force at trial in this case the government converted that into a ban on the defense's use of information and documents provided as part of discovery which the defense had been expressly permitted to utilize at trial Yet the communications between DeathFromAbove and DPR were not mentioned in the government's November 21 2014 letter to the Court did not mention Force at all and did not disclose that he was under a grand jury investigation Also the government's reaction at trial to the defense's efforts to introduce those communications as Defense Exhibit E A874 memorialized in the government's February 1 2015 letter to the Court A707 made it clear that the 48 Case 15-1815 Document 30 01 12 2016 1682738 Page66 of 170 government had not made the connection between Force and DeathFromAbove until the defense sought to introduce DX E See Docket#230 at 24 n 10 Nevertheless at trial the Court improperly permitted the government to use the grand jury investigation of Force as a sword to preclude far more than the mere fact that Force was under investigation employing that excuse to stymie the defense and its attempts to introduce evidence not covered by the Court's pretrial rulings Ultimately the government was permitted - improperly yet repeatedly - to use its bogus rationale for precluding information about Force's and Bridges's corruption as both a sword and shield 9 As a result Ulbricht's ability to present his defense and his Fifth and Sixth Amendment rights incorporated therein were gravely impaired and he was denied a fair trial 9 The government seized full advantage of the situation For instance during summation the AUSA disputed Ulbricht's defense theory arguing that t here were no little elves that put all of that evidence on the defendant's computer T 2166 Yet as it turns out - and which the AUSA knew all along - there were indeed two little elves - law enforcement agents investigating the Silk Road website - operating secretly illegally corruptly and brazenly even inside the Silk Road website itself 49 Case 15-1815 Document 30 01 12 2016 1682738 Page67 of 170 E The Court Abused Its Discretion In Denying Ulbricht's Motion for a New Trial Based on the Government's Failure to Make Complete and Accurate Pretrial Disclosure Regarding Law Enforcement Corruption In the Government's Investigation The issuance of the Force Bridges Complaint just seven weeks after trial in this case confirmed that the government had deliberately withheld from the defense and the Court a substantial volume of critical exculpatory information and material with respect to Force's corruption and information about Bridges's corruption entirely Indeed the Force Bridges Complaint indicates that even now the government has not provided a complete account of Force's and Bridges's misconduct In light of the government's failure to fulfill its constitutional obligation pursuant to Brady - in terms of both the disclosure itself as well as the timing of the limited disclosure the government did make - the Court abused its discretion in denying Ulbricht's Rule 33 motion for a new trial 1 The Principles Applicable to Exculpatory Material and Information a General Principles Governing the Government's Brady Disclosure Obligations As this Court explained most recently in United States v Certified Environmental Services Inc 753 F 3d 72 2d Cir 2014 u nder Brady and its progeny 'the Government has a constitutional duty to disclose favorable evidence 50 Case 15-1815 Document 30 01 12 2016 1682738 Page68 of 170 to the accused where such evidence is material either to guilt or to punishment ' Id at 91 quoting United States v Coppa 267 F 3d 132 139 2d Cir 2001 In that context t here are three components of a true Brady violation 1 The evidence at issue must be favorable to the accused either because it is exculpatory or because it is impeaching 2 that evidence must have been suppressed by the Government either willfully or inadvertently and 3 prejudice must have ensued United States v Jackson 345 F 3d 59 71 2d Cir 2003 quoting Strickler v Greene 527 U S 263 281-82 1999 753 F 3d at 91 See also Thomas 981 F Supp 2d at 238 citing United States v Coppa 267 F 3d at 140 and Moore v Illinois 408 U S 786 794-95 1972 Regarding the prong by which Brady material is defined in Certified Environmental Services the Second Circuit pointed out that evidence is material within the meaning of Brady when there is a reasonable probability that had the evidence been disclosed the result of the proceeding would have been different such that the failure to disclose undermine s confidence in the verdict Cone v Bell 556 U S 449 469-70 2009 quoting Kyles v Whitley 514 U S 419 435 1995 753 F 3d at 91 The standard for the inquiry regarding prejudice as the Supreme Court explicated in Kyles v Whitley asks not whether the defendant would more likely than not have received a different verdict with the evidence but whether in its 51 Case 15-1815 Document 30 01 12 2016 1682738 Page69 of 170 absence he received a fair trial understood as a trial resulting in a verdict worthy of confidence 514 U S at 434 See also Lambert v Beard 537 Fed Appx 78 87 3d Cir 2013 after remand by Wetzel v Lambert __ U S __ 132 S Ct 1195 2012 vacating and remanding 633 F 3d 126 3d Cir 2011 As the Court in Kyles noted a showing of materiality does not require demonstration by a preponderance that disclosure of the suppressed evidence would have resulted ultimately in the defendant's acquittal M ateriality is a reasonable probability of a different result and the adjective is important 514 U S at 434 internal citations omitted See also Thomas 981 F Supp 2d at 242-43 A reasonable probability of a different outcome is not a sufficiency of evidence test and thus does not require that the evidence would have rendered the evidence as a whole insufficient to support a conviction United States v Payne 63 F 3d 1200 1209 2d Cir 1995 quoting Kyles 514 U S at 435 Rather evidence must be disclosed if it could reasonably have been taken to put the whole case in such a different light as to undermine confidence in the verdict Coppa 267 F 3d at 139 quoting Kyles v Whitley 514 U S 419 435 1995 As this Court has held even when evidence may be both inculpatory and exculpatory its disclosure is not thus precluded under Brady See United States v 52 Case 15-1815 Document 30 01 12 2016 1682738 Page70 of 170 Mahaffy 693 F 3d 113 130 2d Cir 2012 t he fact that the government is able to argue that portions of the transcripts were consistent with the prosecution's theory fails to lessen the exculpatory force of the remaining parts see also United States v Rivas 377 F 3d 195 199-200 2d Cir 2004 United States v Thomas 981 F Supp 2d 229 233 S D N Y 2013 w hen Brady material is withheld the Government's case is 'much stronger and the defense case much weaker than the full facts would have suggested' citing Kyles v Whitley 514 U S 419 429 1995 In that context even when exculpatory evidence is disclosed a Brady violation can still occur if the disclosure is untimely As the Court in Thomas stated e vidence is suppressed when the prosecutor does not disclose it 'in time for its effective use at trial ' 981 F Supp 2d at 239 quoting Coppa 267 F 3d at 135 internal citations omitted and citing United States v Avellino 136 F 3d 249 255 2d Cir 1998 The Court in Certified Environmental Services elaborated that t his aspect of Brady affects not only what the Government is obligated to disclose but when it is required to do so Temporally the timing of a disclosure required by Brady is dependent upon the anticipated remedy for a violation of the obligation to disclose the prosecutor must disclose exculpatory and impeachment information no later than the point at which a reasonable probability will exist that the 53 Case 15-1815 Document 30 01 12 2016 1682738 Page71 of 170 outcome would have been different if an earlier disclosure had been made 753 F 3d at 92 quoting Coppa 267 F 3d at 142 Courts have also encouraged prosecutors to err on the side of disclosure for reasons of prudence as well as fairness As the Court in Cone v Bell cautioned a s we have often observed the prudent prosecutor will err on the side of transparency resolving doubtful questions in favor of disclosure 556 U S at 470 citing Kyles 514 U S at 439 Bagley 473 U S 667 711 n 4 Stevens J dissenting United States v Agurs 427 U S 97 108 1976 See also United States v Van Brandy 726 F 2d 548 552 9th Cir 1984 W here doubt exists as to the usefulness of evidence the prosecutor should resolve such doubts in favor of full disclosure As the Court in Thomas recognized questions about the reliability of exculpatory information are judgment calls for a defendant and his counsel not the Government 'to allow otherwise would be to appoint the fox as henhouse guard ' 981 F Supp 2d at 241 quoting DiSimone v Phillips 461 F 3d 181 195 2d Cir 2006 Thus in contemplating whether and when to disclose t he government must bear in mind however that it has the 'affirmative duty to resolve doubtful questions in favor of disclosure ' and that 'if the sword of Damocles is hanging 54 Case 15-1815 Document 30 01 12 2016 1682738 Page72 of 170 over the head of one of the two parties it is hanging over the head of the government ' United States v Hsia 24 F Supp 2d 14 30 D D C 1998 quoting United States v Blackley 986 F Supp 600 607 D D C 1997 internal quotations omitted Here though when Brady becomes an issue in the pretrial context disclosure has a broader context Thus when the exculpatory character harmonize s with the theory of the defense case failure to disclose that evidence constitutes a Brady violation Id quoting United State v Triumph Capital Grp 544 F 3d 149 164 2d Cir 2008 That harmony with defense theories here was detailed pretrial during trial and in the Rule 33 motion Also the timeliness requirement incorporated in the Brady disclosure obligation compels disclosure of materially favorable evidence in sufficient time to permit the defense the opportunity to use it effectively before trial Coppa 267 F 3d at 142 whether the disclosure is made in a timely fashion depends on the sufficiency under the circumstances of the defense's opportunity to use the evidence when disclosure is made see also United States v Solomonyan 451 F Supp 2d 626 644-645 S D N Y 2006 Thus implicit in the government's Brady obligation is the requirement that the defense is able to use the materially favorable evidence even if only to uncover additional exculpatory evidence See e g United States v Gil 297 F 3d 93 104 55 Case 15-1815 Document 30 01 12 2016 1682738 Page73 of 170 2d Cir 2002 materially favorable evidence even if not admissible itself must be disclosed pursuant to Brady if it could lead to admissible evidence Indeed in Gil the inclusion of critical exculpatory and impeachment information in boxes of documents produced pursuant to 18 U S C 3500 the weekend prior to trial was deemed insufficient notice Id at 106-07 Consequently although there are interests in maintaining grand jury secrecy that exist while an investigation is ongoing unsealing was necessary here because evidence of Force's misconduct was exculpatory and thus Brady material the use of which was necessary to avoid a possible injustice See generally Douglas Oil Co Of California v Petrol Stops Northwest 441 U S 211 1979 requiring a showing that material sought is needed to avoid a possible injustice in another judicial proceeding that the need for disclosure is greater than the need for continued secrecy and that their request is structured to cover only material so needed Certainly the right to pre-trial access to Brady material presents a particularized and or compelling need for its unsealing See e g United States v Youngblood 379 F 2d 365 367 2d Cir 1967 see also Dennis 384 U S at 868-70 disclosure rather than suppression of relevant materials ordinarily promotes the proper administration of criminal justice Moreover delaying disclosure until it is contemporaneous with production of 3500 material does not absolve the government of its responsibility to disclose 56 Case 15-1815 Document 30 01 12 2016 1682738 Page74 of 170 exculpatory material and information in time for the defense's effective use at trial As the Court in Hsia recognized the existence of a duty to disclose witness statements at trial pursuant to the Jencks Act 18 U S C 3500 does not eviscerate the government's Brady obligation to disclose witness statements well in advance of trial if portions of those statements also fall under Brady 24 F Supp 2d at 29 citing United States v Tarantino 846 F 2d 1384 1414 n 11 D C Cir 1988 As the Court in Hsia pointed out t his is important because the government is required to disclose Brady material in sufficient time for the defendant to 'use the favorable material effectively in the preparation and presentation of its case ' United States v Pollack 534 F 2d 964 973 D C Cir 1976 while Jencks material is not required to be disclosed until after the witness has testified 24 F Supp 2d at 29 See also Thomas 981 F Supp 2d at 241 t he Government's argument conflates its Jencks Act and Brady obligations While those responsibilities overlap at times they are distinct legal concepts The Jencks Act is concerned with discovery to be produced by the Government Brady is concerned with fairness The Court in Thomas further recognized a reactive defense maneuver after a late Brady disclosure is no substitute for thoughtful preparation and a considered strategy Brady material must be provided to a defendant 'in time for its effective use at trial ' 981 F Supp 2d at 242 quoting Coppa 267 F 3d at 135 emphasis 57 Case 15-1815 Document 30 01 12 2016 1682738 Page75 of 170 supplied by Court in Thomas and citing Grant v Alldredge 498 F 2d 376 382 2d Cir 1974 refusing to infer from the failure of defense counsel when surprised at trial to seek time to gather other information on the suppressed witness that defense counsel would have by-passed the opportunity had the prosecutor apprised him of the evidence at a time when the defense was in a reasonable pre-trial position to evaluate carefully all the implications of that information As this Court explained in Leka v Portuondo 257 F 3d 89 2d Cir 2001 t he opportunity for use under Brady is the opportunity for a responsible lawyer to use the information with some degree of calculation and forethought Id at 101-03 See also Thomas 981 F Supp 2d at 240 St Germain v United States Nos 03 cv 8006 CM 99 cr 339 CM 2004 WL 1171403 at 18 S D N Y May 11 2004 defense strategies are largely formed prior to trial and the necessary predicate is that the strategies selected were chosen after careful consideration of all constitutionally-compelled disclosure Consequently as this Court realized in Leka w hen such a disclosure is first made on the eve of trial or when trial is under way the opportunity to use it may be impaired The defense may be unable to divert resources from other initiatives and obligations that are or may seem more pressing And the defense may be unable to assimilate the information into its case 58 Case 15-1815 Document 30 01 12 2016 1682738 Page76 of 170 257 F 3d at 101 citing United States v Washington 294 F Supp 2d 246 250 D Conn 2003 government's failure to disclose evidence impeaching the central witness until after the first day of trial prejudiced defendant because the late disclosure prevented defense counsel from investigating and planning overall trial strategy 10 b The Manner of the Government's Brady Disclosure Obligations In Thomas the Court also emphasized the importance of the manner of the Government's disclosure 981 F Supp 2d at 240 citing Gil 297 F 3d at 93 labeling Brady evidence as 3500 material and producing it as part of a large 3500 production on the eve of trial constitutes suppression and United States v Breit 767 F 2d 1084 1090 n 4 4th Cir 1985 government may not discharge its Brady obligation merely by tendering a witness without providing any indication that the witness's testimony may be helpful to defense 10 Indeed even in Certified Environmental Services in which this Court did not find a Brady violation because inter alia the notes at issue were at best marginally helpful to the defense 753 F 3d at 93 and the undisclosed reference in the notes was not inconsistent with the prior testimony id the Court nevertheless added that t his is not to suggest however that the prosecutors did nothing wrong in failing to disclose the handwritten notes along with the typewritten summaries To begin with we see no reason - and the Government offers none - why the prosecutors here could not and should not have acted in favor of disclosing the Brady material earlier Id quoting United States v Rittweger 524 F 3d 171 182 2d Cir 2008 59 Case 15-1815 Document 30 01 12 2016 1682738 Page77 of 170 In that context the Government cannot hide Brady material as an exculpatory needle in a haystack of discovery materials 981 F Supp 2d at 239 citing United States v Skilling 554 F 3d 529 577 5th Cir 2009 aff'd in part and vacated in part on other grounds 561 U S 358 2010 suggesting that Brady violations related to voluminous open file discovery depend on what the government does in addition to allowing access to a voluminous open file See also Hsia 24 F Supp 2d at 29-30 g overnment cannot meet its Brady obligations by providing 600 000 documents and then claiming that the defendant should have been able to find the exculpatory information 2 The Government Failed to Make Timely Production of Exculpatory Material Thus the Court should have granted Ulbricht's Rule 33 motion because the government failed to produce exculpatory material in a timely fashion that would have permitted the defense effective use of the material and information at trial Moreover while the government's intent is not required for a Brady violation here the government's concealment was willful and calculated It provided but the tip of the iceberg of information it possessed regarding Force and none regarding Bridges That constituted material non-disclosure that was only aggravated by the government's manipulation of the time frame to delay the formal charging of Force and Bridges until after Ulbricht's trial had concluded 60 Case 15-1815 Document 30 01 12 2016 1682738 Page78 of 170 In that regard within the 5 000 pages of 3500 material for the government's first witness SA Jared Der-Yeghiayan produced less than two weeks prior to trial and after the Court had precluded any defense reference to the Force investigation and misconduct - and in some instances 30 months after the information was memorialized by SA Der-Yeghiayan and in most instances close to or more than two years after - resided a substantial volume of exculpatory material and information That information was directly relevant not only to the government's claim that Force's investigative activities and misconduct were independent of the SDNY prosecution but also to Ulbricht's defense that he was not DPR Ulbricht's Rule 33 motion included a catalog of the 3500 material that is exculpatory and which was not disclosed prior to the onslaught of 3500 material serially produced in the weeks before trial A643 As that list demonstrates 70 separate documents some consisting of multiple pages in the 3500 material contained exculpatory material and information that was not provided to the defense at a time in which it could be used effectively at trial Nor can it be disputed that the information about an alternate perpetrator discussed further post constituted Brady material See Leka v Portuondo 257 F 3d at 99 Brady material is of a kind that would suggest to any prosecutor that the defense would want to know about it See also Thomas 981 F Supp 2d at 238-39 Indeed in Lambert v Beard 537 Fed Appx 78 81-82 3d Cir 2013 the 61 Case 15-1815 Document 30 01 12 2016 1682738 Page79 of 170 nondisclosure related to notes reflecting that unbeknownst to either the defense or the jury at the time a critical government witness had in fact supplied police with another perpetrator See also Cone v Bell 556 U S at 471 undisclosed investigative reports containing information consistent with defense theory were deemed Brady material Here as well the cumulative effect of the untimely disclosure amplified its impact and the prejudice suffered by Ulbricht as a result See Cone v Bell 556 U S at 475 i t is possible that the suppressed evidence viewed cumulatively may have persuaded the jury not to impose the death sentence on the defendant footnote omitted id at 471 both the quantity and the quality of the suppressed evidence lends support to the defendant's position Judge Alex Kozinski in dissenting from the denial of a petition for rehearing declared that t here is an epidemic of Brady violations abroad in the land and o nly judges can put a stop to it United States v Olsen 737 F 3d 625 626 9th Cir 2013 denying reh'g Kozinski J dissenting See also id at 631 Brady violations have reached epidemic proportions in recent years and the federal and state reporters bear testament to this unsettling trend As a result in prescribing a solution Judge Kozinski urged the courts to send prosecutors a clear message Betray Brady give short shrift to Giglio and you will lose your ill-gotten conviction Id at 633 62 Case 15-1815 Document 30 01 12 2016 1682738 Page80 of 170 Accordingly in addition to the initial pretrial and trial errors the Court abused its discretion in denying Ulbricht's Rule 33 motion for a new trial based on the government's failure to disclose exculpatory material and information and or to do so in a timely manner that would have permitted the defense to make use of it POINT II THE COURT ABUSED ITS DISCRETION BY CURTAILING CROSS-EXAMINATION AND THE DEFENSE THEORY AT TRIAL A HSI SA Jared Der Yeghiayan During cross-examination of the government's first and principal witness SA Der-Yeghiayan - through whom the government introduced a substantial volume of Exhibits from the Silk Road website and the parameters of the government's investigation from intercepting drugs shipped from overseas vendors to U S customers to Silk Road chats forum posts and administrative functions - the government began to object to inquiries about the investigation generally in particular with respect to Mark Karpeles on whom SA Der-Yeghiayan had focused and developed a significant amount of information by the Fall of 2013 The Court's initial reaction was that the subject matter of the cross-examination was highly relevant A406 and that it went to SA Der-Yeghiayan's state of mind A407 The Court added that the inquiry was 63 Case 15-1815 Document 30 01 12 2016 1682738 Page81 of 170 in the heartland of the defense id and was not hearsay because it was not being offered for the truth A411 The Court added I don't think it's irrelevant because if he pursued a target of this conduct and it wasn't the defendant I think that's directly relevant to the defendant's theory of the case A416 See also A412 id at A416 t hey're trying to raise a reasonable doubt as to whether or not the defendant is the real DPR At that juncture the Court adjourned for the weekend and invited letters from both sides Monday morning the Court performed a complete about-face ruling that the cross-examination was not proper for purposes of raising the prospect of an alternative perpetrator or to challenge the competency of the investigation A420-441 The Court invited the government to submit a list of questions and answers to be stricken and granted the strikes proposed A441-443 A466-471 The Court refused to afford defense counsel any time to review the stricken sections to determine whether the cross-examination could be reconstructed through questions the Court would permit A471-73 Regarding the alternative perpetrator the Court found the defense had not established a direct connection between Mark Karpeles and the charged offenses - essentially imposing on the defense the obligation to prove that Karpeles was 64 Case 15-1815 Document 30 01 12 2016 1682738 Page82 of 170 DPR A423-30 The Court ignored the other purpose of the questioning to expose the defects in the investigation that allowed Karpeles to escape prosecution and instead turned attention to Ulbricht which in turn also implicated Force's and Bridges's corruption The Court also ruled that the cross-examination would be curtailed because the government's redirect would be constrained you can't have one side one-hand clapping A428 However the alternative perpetrator line of inquiry should have been permitted to continue and the prior testimony not stricken because it was consistent with the case law on alternate perpetrators in some instances not hearsay at all and in other respects admissible under Rules 807 and 403 Fed R Evid 65 Case 15-1815 Document 30 01 12 2016 1682738 Page83 of 170 1 In Curtailing and Striking Cross Examination of SA DerYeghiayan the Court Improperly Concluded There Was No Nexus Between the Alternative Perpetrator and the Specific Offenses Here case law supports Ulbricht's right to ask SA Der-Yeghiayan further questions about alternative perpetrators including Karpeles The cases cited by the Court and the government to the extent they support the broad principles asserted by the government apply when it is the defendant and not an alternative perpetrator who is protected by constitutional as well as evidentiary rules and in which - unlike herein - there was not any nexus between the alternative perpetrator and the specific offenses alleged a Relevant Case Law Regarding An Alternate Perpetrator Pointing to an alternative perpetrator is a defense endorsed by the Supreme Court and other courts time and again and the defense was utilizing evidence to that effect consistent with the rules of evidence and Ulbricht's constitutional right to present a defense which sometimes supersedes the technical limits of those evidentiary rules See e g Kyles v Whitley 514 U S 419 449 n 19 453 Boyette v LeFevre 246 F 3d 76 91 2d Cir 2001 Indeed as set forth in Wade v Mantello 333 F 3d 51 57 2d Cir 2003 the Supreme Court has observed on more than one occasion ''at a minimum criminal defendants have the right to put before a jury evidence that might influence the determination of guilt '' Id quoting Taylor v Illinois 484 U S 400 66 Case 15-1815 Document 30 01 12 2016 1682738 Page84 of 170 408 1988 quoting Pennsylvania v Ritchie 480 U S 39 56 1987 In that regard t he Constitution protects a criminal defendant from the arbitrary exclusion of material evidence and evidence establishing third-party culpability is material Wade 333 F 3d at 58 11 In addition the Court placed too high a burden on the defense with respect to evidence of an alternative perpetrator In each of the cases the government cited and the Court relied upon there was a failure to establish the necessary nexus between the alleged third-party perpetrator and the crime charged See Wade v Mantello 333 F 3d at 61 testimony in murder case that third-party was involved in unrelated shoot-out with victim weeks earlier was properly excluded at trial because w eighed against the limited probative value of the proffered testimony were dangers that the jury could have been misled or confused by the testimony emphasis added DiBenedetto v Hall 272 F 3d 1 7-8 1st Cir 2001 absent evidence of a connection between the other perpetrators and the crime not mere speculation on the part of the defendant Court excluded evidence in murder trial related to another murder meant to establish that third party culprits not the defendant and his co-defendant were guilty People of Territory of Guam v 11 See also Mendez v Artuz 303 F 3d 411 413 2d Cir 2002 noting materiality of evidence of an alternative culprit United States v Manning 56 F 3d 1188 1198 9th Cir 1995 same Bowen v Maynard 799 F 2d 593 600-601 610-613 10th Cir same United States v Stifel 594 F Supp at 1541 same 67 Case 15-1815 Document 30 01 12 2016 1682738 Page85 of 170 Ignacio 10 F 3d 608 615 9th Cir 1993 trial court did not abuse its discretion by excluding evidence of third-party's suicide as evidence of third-party culpability where defendant had not provided substantial evidence connecting third-party to the crime charged internal quotation omitted Andrews v Stegall 11 Fed Appx 394 396 6th Cir 2001 distinguishing defendant's claim of third party culpability in murder case involving a vague threat by third party made some unknown time before the murder to the victim's stepson where the third-party was not shown to have been anywhere near the scene of the crime and was not available to testify from Chambers 410 U S at 300-301 in which there was substantial evidence directly connecting the third-party with the offense United States v Diaz 176 F 3d 52 82 2d Cir 1999 trial court properly excluded evidence of another crime - prison records showing that the murder victim had assaulted a third-party while in prison more than a year prior - in order to suggest motive on the part of a third party in the charged crime because standing alone it would be creative conjecturing and the evidence speculative United States v Wade 512 Fed Appx 11 14 2d Cir 2013 the district court reasonably excluded testimony about a third party's arrest because the third party's December 3 2009 sale of drugs from a mailbox was not temporally or physically linked to the May 11 2009 drug and firearm seizures from the defendant's girlfriend's apartment that were contemporaneous with the defendant's arrest 68 Case 15-1815 Document 30 01 12 2016 1682738 Page86 of 170 and the testimony therefore presented a risk of juror confusion and extended litigation of a collateral matter b The Requisite Nexus Was Established By the Government Itself Through Its Direct Examination of SA Der-Yeghiayan In this case though the government itself in the person of SA Der-Yeghiayan and others provided the requisite nexus between the alternate perpetrator and specific offenses here via an analysis of documentary and other materials and the defense via cross-examination was simply cataloguing the bases for that nexus Ultimately the Court's position and government's argument was about the weight of the evidence which of course was for the jury to determine Moreover here parts of the defense mirrored to a significant extent that endorsed in Kyles v Whitley in which the defense alleged the defendant had been framed by an informant for the purposes of shifting suspicion away from himself for the offense charged against the defendant 514 U S at 429 This case also replicates circumstances in other cases in which this Court reversed convictions because alternative perpetrator evidence was excluded See Alvarez v Ercole 763 F 3d 223 2d Cir 2014 conviction reversed because defense counsel not permitted to cross-examine detective about police report containing information about the alternative suspect Cotto v Herbert 331 F 3d 69 Case 15-1815 Document 30 01 12 2016 1682738 Page87 of 170 217 229 2d Cir 2003 b y prohibiting defense counsel from questioning Detective Alfred about the police report the trial court allowed the jury to get the impression that the defense had nothing other than rhetoric to contradict the prosecutor's statement in summation that the NYPD's investigation into the charged murder was 'thorough' citing Davis v Washington 415 U S 308 318 1974 Thus here the evidence regarding an alternative perpetrator is directly related to the offenses alleged and is neither collateral nor speculative Again the weight of such evidence which ultimately is the government's primary concern throughout its letter is a matter for the jury to determine Stifel 594 F Supp at 1541 2 The Court Also Erred by Disregarding the Untimeliness of the Government's Objections Failing to Acknowledge That Cross Examination of SA Der-Yeghiayan Was Relevant to Another Proper Defense Ulbricht Was Presenting and Improperly Considering Issues Regarding the Government's Possible Redirect In addition the government's objections were untimely The government provided 5 000 pages of material pursuant to 18 U S C 3500 for SA Der-Yeghiayan a substantial portion of which was devoted to government's investigation of Karpeles It is inconceivable that the government did not anticipate the line of cross-examination Yet it did not make a motion in limine 70 Case 15-1815 Document 30 01 12 2016 1682738 Page88 of 170 did not object to defense counsel's opening nor during a significant portion of the cross-examination of SA Der-Yeghiayan Further as noted ante the questioning of SA Der-Yeghiayan was relevant to another proper defense Ulbricht was presenting - that of the conduct of the government's investigation - which the Court did not address See United States v Blake 107 F 3d 651 653 8th Cir 1997 12 The Court also abused its discretion in focusing on issues regarding the government's possible redirect That simply was not a proper consideration and therefore cannot be located within the range of permissible decisions United States v Figueroa 548 F 3d 222 226 2d Cir 2008 3 The Court Abused Its Discretion by Precluding the Defense From Eliciting from SA Der-Yeghiayan that Karpeles Attempted to Exchange Immunity for the Identity of DPR Still another area of cross-examination of SA Der-Yeghiayan that the Court precluded with its ruling was eliciting from SA Der-Yeghiayan that he was told by AUSA's that Karpeles's lawyers had offered to provide the name of the person 12 In that context due to the government's precipitous seizure of one of Karpeles's accounts in May 2013 Karpeles had notice that he was under investigation in some respect thereby giving him ample time to cover his own tracks - a danger SA Der-Yeghiayan himself warned of in protesting not only the seizure but also any further negotiations with Karpeles Again such a defense is recognized as valid and appropriate See Kyles v Whitley 514 U S at 442 n 13 if defense had possessed the undisclosed material the defense could have attacked the investigation as shoddy id at 445-46 Bowen v Maynard 799 F 3d 593 613 10th Cir 1986 a common trial tactic of defense lawyers is to discredit the caliber of the investigation Cotto v Herbert 331 F 3d 217 229 2d Cir 2003 71 Case 15-1815 Document 30 01 12 2016 1682738 Page89 of 170 Karpeles - who controlled the world's primary bitcoin exchange - suspected of being DPR if the government would forego charges against Karpeles for operating unlicensed money exchanging operations A432-433 A341 As a threshold matter the government's letter seeking to prohibit that inquiry A307 verified precisely what defense counsel sought to elicit from SA Der-Yeghiayan about the offer on cross-examination and which was conveyed in July 2013 by Karpeles's lawyer to the government in return for immunity from prosecution by the U S Karpeles offered to provide a name of someone he suspected was operating Silk Road A311 Nowhere in its letter did the government challenge the accuracy of that account In fact the government confirmed it As the Court noted the initial offer from Karpeles's attorney was not hearsay as it was not being offered for the truth of the matter A405-410 However the exchanges between AUSA's and SA Der-Yeghiayan while hearsay qualified for admission under Rule 807 Fed R Evid particularly in light of the government's failure to challenge their accuracy Thus the analysis for purposes of Rule 807had been satisfied Furthermore exceptional circumstances warranted application of Rule 807 here Karpeles is a French citizen living in Japan His lawyers have not been identified nor have the AUSA's who relayed the statement to SA Der-Yeghiayan 72 Case 15-1815 Document 30 01 12 2016 1682738 Page90 of 170 See e g Muncie Aviation Corporation v Party Doll Fleet Inc 519 F 2d 1178 1182-83 5th Cir 1975 difficulty in finding witnesses justified admission Limone v United States 497 F Supp 2d 43 62-63 D Mass 2007 Cf Parsons v Honeywell Incorporated 929 F 2d 901 907-08 2d Cir 1991 statement not admissible because declarant available as a witness The circumstances also easily meet the indicia of reliability and trustworthiness requirements found to satisfy the Rule and or its predecessors Rule 803 24 and Rule 804 b 5 For example in Steinberg v Obstetrics-Gynecological Fertility Group P C 260 F Supp 2d 492 D Conn 2003 the Court concluded that the description of the status of a case by one attorney to another assuming control of the case possessed sufficient indicia of reliability and lack of motive to misrepresent Id at 496 See also United States v Dumeisi 424 F 3d 566 576-77 7th Cir 2005 relying on the declarants' duty to accurately record their own activities United States v Bailey 581 F 2d 341 349 3d Cir 1978 consideration should be given to factors bearing on the reliability of the reporting of the hearsay by the witness Muncie Aviation Corporation v Party Doll Fleet Inc 519 F 2d 1178 1182-83 5th Cir 1975 trustworthiness established because published by government without any motive not to tell the truth or be inaccurate United States v Iaconetti 406 F Supp 554 559 E D N Y 1976 admitting statement because it was testified to by a person 73 Case 15-1815 Document 30 01 12 2016 1682738 Page91 of 170 with whom it was appropriate and even necessary for the declarant to communicate Moreover the rules of evidence were not designed to curtail a defendant's constitutional rights as implicated here with respect to confrontation and the right to present a defense and as the Supreme Court declared in Chambers v Mississippi 410 U S 284 1973 where constitutional rights directly affecting the ascertainment of guilt are implicated the hearsay rule may not be applied mechanistically to defeat the ends of justice Id at 302 Thus the offer by Karpeles's lawyer was admissible pursuant to Rule 807 Concerns expressed by the Court regarding context and meaning of the offer are unpersuasive and address merely the weight that should be accorded the statement - contentions appropriately directed to the jury See Stifel 594 F Supp 1525 1541 N D Ohio 1984 t he identity of the bomb sender was a question for the jury and defendant should have been apprised of evidence showing that someone other than himself had equal motive access to materials and other surrounding circumstances implicating him as the guilty party See also Kyles v Whitley 514 U S at 451 prosecution's factual arguments about the implications of exculpatory evidence confuses the weight of the evidence with its favorable tendency 74 Case 15-1815 Document 30 01 12 2016 1682738 Page92 of 170 B FBI Computer Specialist Thomas Kiernan At the time of his testimony Agent Thomas Kiernan had been with the FBI for 23 years and held the position of computer scientist A491 Through Agent Kiernan's testimony the government introduced the entire contents of Ulbricht's laptop A492 During his direct testimony select documents from Ulbricht's hard drive were admitted in evidence and read to the jury See e g A494 495 Agent Kiernan also testified about the operation of Torchat a computer program installed on Ulbricht's laptop at the time of his arrest which was the vehicle for many internet chats introduced by the government and in which the government claimed Ulbricht was a participant A493 During cross-examination however defense counsel was precluded from asking a number of questions directly relevant to material elicited from Agent Kiernan on direct For example Agent Kiernan testified about a test of the Torchat program he conducted to establish that files recovered from Ulbricht's laptop were structured in the same way as files Agent Kiernan generated on his own computer The relevant portion of Agent Kiernan's testimony is as follows Q Have you personally ever used Tor chat A I have Q Have you tested Tor chat A I have 75 Case 15-1815 Document 30 01 12 2016 1682738 Page93 of 170 Q Have you saved the logs of Tor chats on your own computer A I have T 889 The defense should have been permitted to ask Agent Kiernan whether his Torchat program experiment was running on the same kernel version as that on Ulbricht's laptop which would have established that Agent Kiernan's conclusions were flawed but was denied the opportunity A503 The defense was also precluded from asking questions related to the security of BitTorrent T 1054 and about a particular PHP script admitted as Defense Ex J that was recovered from Ulbricht's laptop both clearly within the scope of direct and thus fair game 13 A498 C The Court's Rulings Which Curtailed the Cross Examinations of SA Der-Yeghiayan and Agent Kiernan Constituted an Abuse of Discretion As this Court has instructed trial judges retain wide latitude insofar as the Confrontation Clause is concerned to impose reasonable limits on such cross-examination based on concerns about among other things harassment prejudice confusion of the issues the witness' safety or interrogation that is repetitive or only marginally relevant United States v Crowley 318 F 3d 401 13 BitTorrent is an internet file sharing program which creates an extraordinary vulnerability to internet intrusion by hackers when open During direct of Agent Kiernan a photo of Mr Ulbricht's laptop screen at the time of arrest was introduced which established that the BitTorrent program was indeed open thereby jeopardizing the security of the information on Ulbricht's laptop 76 Case 15-1815 Document 30 01 12 2016 1682738 Page94 of 170 417 2d Cir 2003 cert denied 540 U S 894 2003 citing Delaware v Van Arsdall 475 U S 673 679 1986 An appellate court will reverse the district court's decision to restrict cross-examination only when th e broad discretion of the district court is abused Figueroa 548 F 3d at 226 citing Crowley 318 F 3d at 417 The district court abuses its discretion when 1 its decision rests on an error of law such as application of the wrong legal principle or a clearly erroneous factual finding or 2 its decision - though not necessarily the product of a legal error or a clearly erroneous factual finding - cannot be located within the range of permissible decisions Figueroa 548 F 3d at 226 citations and footnotes omitted see also Koon v United States 518 U S 81 100 1996 Such error is not harmless unless appellate court finds beyond a reasonable doubt that the error complained of did not contribute to the verdict obtained Chapman v California 386 U S 18 24 1967 Accordingly the Court abused its discretion in curtailing the cross-examinations of SA Der-Yeghiayan and Agent Kiernan 77 Case 15-1815 Document 30 01 12 2016 1682738 Page95 of 170 POINT III THE COURT ABUSED ITS DISCRETION IN PRECLUDING TWO DEFENSE EXPERTS During the defense case the Court precluded two defense experts Dr Steven Bellovin and Andreas Antonopoulos The two experts were necessary to rebut 1 portions of the government's case that the defense was precluded from confronting on cross-examination and 2 the testimony of Ilhwan Yum involving a lengthy spreadsheet of thousands of bitcoin transactions and a complex analysis of bitcoin wallets located on the Silk Road servers and Ulbricht's laptop notice of which was provided to the defense only days prior Dr Bellovin's testimony would have addressed a number of technical computer and internet-related issues which the defense was prevented from addressing during cross-examination Those matters included general principles of internet security and vulnerabilities PHP computer programming forensic memory analysis general issues related to linux-based operating systems and principles of public key cryptography Each of these issues was significantly implicated in the testimony of government witnesses as well as in the evidence related to the government's forensic examination and analysis of Ulbricht's laptop Antonopoulos's testimony would have explained to the jury a number of technically complex and abstract concepts involving bitcoin and countered certain 78 Case 15-1815 Document 30 01 12 2016 1682738 Page96 of 170 aspects of Yum's testimony particularly the massive spreadsheet accompanying his testimony Yum's direct testimony involved technically complex concepts related to bitcoin and computer forensics including the extraction of several bitcoin wallet files from Ulbricht's laptop and the Silk Road computer servers It featured a comparative analysis of bitcoin addresses from wallets located on the Silk Road Marketplace server and Ulbricht's laptop A532 He also explained - in some instances incorrectly i e his definition of a hot wallet A555-556 - concepts related to bitcoin in a manner consistent with the government's theory of the case Antonopoulos's testimony was critical to the jury's full understanding of complex concepts related to bitcoin and to highlight defects in Yum's forensic analysis of bitcoin addresses Furthermore his testimony would have defined principles of ownership control and access related to bitcoin and bitcoin wallets in counterpoint to the flawed conclusions in Yum's testimony as well as Yum's inaccurate definitions of important terminology and descriptions of bitcoin mechanics By precluding the defense experts who would have countered the complex testimony regarding bitcoin presented by the government the government witnesses' testimony essentially went unchallenged and Ulbricht was denied his Fifth and Sixth Amendment rights to present a defense 79 Case 15-1815 Document 30 01 12 2016 1682738 Page97 of 170 A The Court's Decision Precluding the Two Defense Experts The Court's principal stated reason for precluding both defense experts was non-compliance with Rule 16 Fed R Crim P i e the timing of defense disclosure and the level of detail describing the experts' anticipated testimony A362-379 Yet as detailed below the Court's rigid application of the Rule 16 disclosure requirements and its imposition of the most extreme sanction available - preclusion altogether - contravened case law and paid insufficient heed to Ulbricht's Sixth Amendment rights as set forth post The ruling further ignored the particular circumstances in this case namely that the defense was attempting to address issues that had become apparent only during trial Thus the Court's decision was entirely asymmetrical - while the government was able to elicit testimony for which cross-examination was precluded and include complex lengthy summary exhibits created mid-trial the defense was not permitted to confront them at all Regarding the preclusion of Dr Bellovin's testimony the Court held that defense counsel's letter regarding the subject of his testimony failed to describe sufficiently his opinions and proposed topics to be covered A374-75 However the defense's letter disclosing Dr Bellovin's proposed testimony contained detailed reasons why each subject area of his testimony was required to respond to areas the defense was precluded from exploring on cross-examination or to meet 80 Case 15-1815 Document 30 01 12 2016 1682738 Page98 of 170 specific government arguments or to augment the defense theories A385 In fact much of Dr Bellovin's testimony was necessitated by testimony the government elicited on direct of its technical computer witnesses in areas that the defense was precluded from examining on cross A388-89 The Court's reasons for precluding Antonopoulos's testimony were similarly in conflict with the record While the Court stated what analysis Antonopoulos performed and the methodology are unknown A368 the defense's letter to the Court sufficiently outlined those subjects and noted that further details awaited Antonopoulos's disembarkation from his trans-Atlantic flight to New York Counsel also made a subsequent detailed oral proffer but to no avail T 1845-1851 The Court ruled that it would be essentially unfair to make the government prepare to cross-examine expert witnesses on short notice A369 Yet the Court's characterization of the defense strategy as trial by ambush A368 was in fact the exact opposite of how events unfolded at trial Indeed many of the exhibits introduced during Yum's testimony were first revealed to the defense mid-trial only three days before their introduction through Yum as a witness Many in the 600 series - including GX 620 a 63-page spreadsheet including and analyzing thousands of bitcoin transactions - were first turned over January 28 2015 more than two weeks into trial and two days prior to 81 Case 15-1815 Document 30 01 12 2016 1682738 Page99 of 170 Yum's testimony Nor were they contained in any previous Exhibit list indeed as former Special Agent Yum testified he had at the prosecutors' direction commenced and completed the spreadsheet and the analysis only after the trial had begun The defense had not even been made aware of any bitcoin wallet analysis let alone provided with related exhibits until 10 17 p m the night of January 25 2015 when a 3MB Excel spreadsheet containing the wallet analysis conducted by Yum was provided to defense counsel See Rule 33 Motion at 14 Docket#224 At that time the government notified defense counsel that the government intended to produce the spreadsheet as 3500 material and was in the process of preparing a series of summary exhibits based on the spreadsheet to be introduced during Yum's testimony Id at 15 14 Furthermore in contrast to the inflexible standard imposed on Ulbricht the government was permitted to elicit Yum's testimony which included the voluminous spreadsheet and an extraordinarily complex analysis of millions of bitcoin addresses and sophisticated computer software The defense sought to call Antonopoulos for the purpose of countering the testimony of Yum who admitted on cross that 60% of the work on the spreadsheet and analysis had been performed 14 A disk containing the documents that would ultimately become GX 650 and 651 was also first provided to defense counsel the night of January 25 2015 82 Case 15-1815 Document 30 01 12 2016 1682738 Page100 of 170 by a colleague with a doctorate in cryptology who the government did not call as a witness at trial A553 When defense counsel asked for a brief adjournment so that a proper cross-examination could be prepared on the materials underlying Yum's testimony the Court refused Thus it was the defense that was subject to trial by ambush A551 B The Court Abused Its Discretion In Precluding the Two Defense Experts It is well established that precluding an expert witness constitutes reversible error if the proposed expert's testimony was critical to the defendant's case and could have produced a different outcome at trial See e g Crane v Kentucky 476 U S 683 690 1986 Constitution guarantees criminal defendants a meaningful opportunity to present a complete defense internal quotations marks and citations omitted Chambers v Mississippi 410 U S 284 302-03 1932 exclusion of evidence amounts to constitutional error if it deprives the defendant of a fundamentally fair trial Whether exclusion of witness testimony constitutes reversible error rests on whether the omitted testimony creates a reasonable doubt that did not otherwise exist United States v Agurs 427 U S 97 112 1976 In addition trial courts have broad discretion in fashioning a remedy for failures to comply with Rule 16 Fed R Crim P Rule 16 United States v 83 Case 15-1815 Document 30 01 12 2016 1682738 Page101 of 170 Chavez 549 F 3d 119 129 2d Cir 2008 United States v Thai 29 F 3d 785 804 2d Cir 1994 The trial court's decisions in its choice of remedy is reviewed under the abuse of discretion standard and is reversible error if it causes substantial prejudice Thai 29 F 3d at 804 see also Zerega Ave Realty Corp v Hornbeck Offshore Transp LLC 571 F 3d 206 213 2d Cir 2009 Although trial courts are afforded deference in sanctioning of parties that do not comply with procedural rules courts have noted that preclusion of evidence is an extreme remedy Hein v Cuprum S A De C V 53 Fed Appx 134 137 2d Cir 2002 commending trial judge for appropriately us ing his discretion to steer a middle course between the extreme remedy of exclusion and the possibility of unfair prejudice to the plaintiff emphasis added Thai 29 F 3d at 806 finding that extreme sanction of striking testimony from the record is the most severe remedy a court can impose short of declaring a mistrial quoting United States v Rodriguez 765 F 2d 1546 1557 11th Cir 1985 internal quotes omitted In determining when the trial court's decision to preclude a witness constituted an abuse of discretion four factors are considered 1 the party's explanation for the failure to comply with the discovery order 2 the importance of the testimony of the precluded witness 3 the prejudice suffered by the opposing party as a result of having to 84 Case 15-1815 Document 30 01 12 2016 1682738 Page102 of 170 prepare to meet the new testimony and 4 the possibility of a continuance Zerega Ave Realty Corp 571 F 3d at 213 Applying these four factors to the facts at hand even assuming non-compliance with procedural rules the Court's reliance on the extreme remedy of preclusion was an abuse of discretion As set forth above the testimony of Dr Bellovin became necessary during the course of trial because the defense was precluded from cross-examining Agent Kiernan on a number of subjects well within the scope of his direct examination See ante at 77 These subjects included the impact of certain lines of PHP computer code the security implications of BitTorrent software on Ulbricht's laptop and the general operation of linux-based operating systems also present on the laptop Antonopoulos's testimony was necessary to counter Yum's testimony which involved a huge spreadsheet and complex analysis of a large number of bitcoin transactions provided to the defense mere days before his testimony The two experts' testimony was critical given the curtailment of cross-examination of Agent Kiernan and the complexity of Yum's testimony involving bitcoin forensics as well as the timing of its production 85 Case 15-1815 Document 30 01 12 2016 1682738 Page103 of 170 Additionally the government fully aware of the subjects the defense experts intended to cover through numerous sidebar discussions and letters to the Court failed to articulate specific prejudice that would have resulted if the expert testimony had been admitted - particularly if the government were granted a continuance to which the defense would have consented For example in United States v Onumonu 967 F 2d 782 784 2d Cir 1992 the defense to a charge of knowingly importing heroin into the United States was that the defendant believed he was smuggling diamonds and therefore lacked the requisite knowledge and intent Id Defendant proffered a gemologist's expert testimony on issues including the feasibility of smuggling diamonds by swallowing them and their value Id at 785 In Onumonu this Court held that the refusal to allow the expert testimony was reversible error because a t the end of the case all the defendant had been able to present was his own belief about diamonds Id at 789 Furthermore a major thrust of the prosecutor's summation was that Onumonu's story was 'ludicrous ' with the government arguing that no one would smuggle diamonds in this fashion Id 15 15 As a result of the preclusion of the experts the government was granted similar license during closing argument in this case T 2154 86 Case 15-1815 Document 30 01 12 2016 1682738 Page104 of 170 This Court found in Onumonu that the exclusion of the expert testimony was not harmless error because the defendant was deprived of fair opportunity to present his case to the jury and the exclusion may have had a substantial effect on the jury's verdict Id see also United States v McBride 786 F 2d 45 49-50 2d Cir 1986 reversing the defendant's conviction because the testimony of a psychiatrist - the only witness the defendant sought to present and who would have testified to the defendant's mental capabilities at the time of the crime - was excluded despite being critical to the defense Similarly in United States v Dwyer 539 F 2d 924 2d Cir 1976 this Court reversed the exclusion of the defense's expert psychiatric testimony related to the role of mental disease or defect in criminal responsibility Dwyer 539 F 2d at 927 Given that the defendant had admitted the criminal conduct alleged expert testimony supporting the assertion that defendant suffered from mental disease or defect was vital Id Therefore the expert opinion would have added to the lay testimony already before the jury and possibly produced a different verdict Id at 927-28 This Court reasoned that because the probative value of the evidence proffered was so great it should not have been excluded in the absence of a showing of unfair prejudice Id at 928 citing United States v Mejia 529 F 2d 995 996 9th Cir 1975 87 Case 15-1815 Document 30 01 12 2016 1682738 Page105 of 170 In a case with very similar facts to Onumonu the defendant charged with importing heroin presented the defense that he believed he was smuggling gold dust United States v Diallo 40 F 3d 31 33-34 2d Cir 1994 The defendant was precluded from presenting the testimony of a commodities consultant regarding the profitability of smuggling gold dust into the country and on general statistics of trading of precious metals Id at 34 In Diallo because the critical fact in issue was whether or not the defendant actually knew what he was smuggling the exclusion of the expert's testimony deprived the defendant of a fair opportunity to present his case to the jury as it left him with only his own testimony to support his defense Id at 35 quoting Onumonu 967 F 2d at 789 Depriving the defendant of this fair opportunity had a substantial effect on the jury's verdict and was therefore found not to be harmless Diallo 40 F 3d at 35 quoting Onumonu 967 F 2d at 789 Particularly analogous to this case was the inequitable nature of the preclusion of the defense expert in Diallo because as this Court pointed out the government was permitted in Diallo to call its own expert - a DEA agent - to establish an economic motive for the defendant to have smuggled heroin and the defense expert would have testified to the economic advantages of smuggling gold dust 40 F 3d at 35 88 Case 15-1815 Document 30 01 12 2016 1682738 Page106 of 170 In the final paragraph of its opinion this Court found that h aving allowed the government to call as an expert a DEA agent who was surely no more qualified as an expert in heroin than the defense's expert witness was in gold the district court should have accorded the defendant the same right Id emphasis added As this Court concluded t urnabout is fair play even in the federal court Id Accordingly the preclusion of two defense experts at trial herein denied Ulbricht his Fifth and Sixth Amendment rights to present a defense While the government was permitted to present testimony regarding extremely complicated processes outside the ken of the average juror Ulbricht was denied the vital opportunity to challenge that testimony and evidence some of which was generated and provided only mid-trial shortly before its admission and therefore the Court's preclusion of the two defense experts was an abuse of discretion Accordingly Ulbricht's convictions should be vacated and a new trial ordered 89 Case 15-1815 Document 30 01 12 2016 1682738 Page107 of 170 POINT IV THE COURT ABUSED ITS DISCRETION IN PRECLUDING ADMISSION OF ANDREW JONES'S STATEMENT AGAINST PENAL INTEREST PURSUANT TO RULE 804 3 b FED R EVID AND OR RULE 807 FED R EVID A Pretrial Disclosure of Andrew Jones's Exculpatory Statement Just two weeks before trial commenced the government wrote defense counsel December 29 2014 to inform of a statement made by Andrew Jones a k a inigo an administrator of the Silk Road site for a period in 2013 until its closure and a cooperating government witness charged in a separate indictment a t some point in or about August or September 2013 Jones tried to authenticate that the Silk Road user Dread Pirate Roberts whom he was talking to at the time via Pidgin chat was the same person with whom he had been communicating in the past with this username Previously in or about October 2012 Jones and Dread Pirate Roberts had agreed upon a handshake to use for authentication in which Jones would provide a certain prompt and Dread Pirate Roberts would provide a certain response When during the 2013 chat in question Jones provided what he believed to be the designated prompt Dread Pirate Roberts was unable to provide the response Jones thought they had agreed on However later in the chat Jones asked Dread Pirate Roberts to validate himself by specifying the first job that Dread Pirate Roberts assigned to him running the DPR Book Club which Dread Pirate Roberts was able to do A398 90 Case 15-1815 Document 30 01 12 2016 1682738 Page108 of 170 That statement substantially buttressed the defense theory that there was more than one DPR that DPR's identity changed over time and that there was a change very close in time to Ulbricht's arrest - all supporting Ulbricht's defense that he had been framed by the genuine DPR B The Trial Proceedings While Jones was included in the government's witness list the government indicated during trial it would not call him A563 As a result the defense indicated its wish to call him but Jones's lawyer informed defense counsel that Jones would not testify and would instead assert his Fifth Amendment privilege A1856 Although the government initially agreed to stipulate to Jones's statement the night before the defense sought to finalize and introduce the stipulation the government reneged at 11 00 p m even though it had in return for the agreement to stipulate extracted a significant concession from the defense earlier that evening A564 Consequently the defense moved for admission of Jones's statement as a statement against penal interest pursuant to Rule 803 4 Fed R Evid or in the interests of justice pursuant to Rule 807 Fed R Evid the residual exception A564 Ulbricht also moved for the statement's admission pursuant to the Fifth Amendment's Due Process guarantee See Chambers v Mississippi 410 U S 284 302 1973 91 Case 15-1815 Document 30 01 12 2016 1682738 Page109 of 170 The Court denied the application to introduce Jones's statement concluding it was not against penal interest because made while Jones was cooperating with the government it was not sufficiently corroborated and did not possess sufficient indicia of trustworthiness A581-583 C The Court Abused Its Discretion In Precluding Admission of Jones's Statement Under Either Rule 804 3 b or Rule 807 Jones's unavailability was established during the colloquy with the Court A587-88 during which defense counsel relayed a conversation with Jones's attorney confirming that Jones would be asserting his Fifth Amendment privilege United States v Chan 184 F Supp 2d 337 341 S D N Y 2002 a witness need not be physically brought into court to assert the privilege the representation that the pleading defendants' lawyers had been contacted and stated that his client would assert the Fifth Amendment privilege is sufficient citing United States v Williams 927 F 2d 95 98-99 2d Cir 1991 Regarding Jones's statement the Court found it was not against his penal interest because he was under a cooperation agreement at the time the statement was made A589 Although the Court relied on unspecified case law id this Court in fact frequently refrain s from articulating the limits of the 'against penal interest' requirement and instead decide s cases based on the corroboration 92 Case 15-1815 Document 30 01 12 2016 1682738 Page110 of 170 requirement United States v Camacho 163 F Supp 2d 287 299 n 10 S D N Y 2001 collecting cases Here Jones's cooperation did not affect his statement's character against his penal interest Cooperation agreements do not provide immunity and regarding an offense involving nationwide and even worldwide illegal internet activity prosecutions could very well occur in multiple jurisdictions In that context of crucial importance is that the agreements explicitly binds only the signing parties leaving cooperators exposed to prosecution for crimes confessed over the course of cooperation in any other jurisdiction including states See United States v Fuller 149 F Supp 2d 17 22-23 S D N Y 2001 cooperator's agreement with state prosecutor did not bar federal prosecution nor prohibit use of cooperator's statements in federal prosecution as agreement is not the equivalent of an 'immunity order ' binding on both the State and Federal Government Consequently a cooperation agreement does not erase Fifth Amendment protections Indeed if it did Jones's invocation of the privilege at trial - a common occurrence for witnesses including those who have cooperated but are not called at trial and who have pleaded guilty but are awaiting sentencing - would not have been valid If his Fifth Amendment privilege survived his cooperation agreement certainly his subsequent incriminating statements were contrary to his penal interest 93 Case 15-1815 Document 30 01 12 2016 1682738 Page111 of 170 In addition even with respect to the prosecuting office that signs the agreement the formal written terms of cooperation provide only conditional protection against subsequent prosecution If at any point the prosecuting office determines a cooperator has been untruthful or provided incomplete information or has committed an additional crime even if not prosecuted the prohibition on prosecution by that office is void See United States v Ming He 94 F 3d 782 790 2d Cir 1996 government was in a position to impose grave penalties if it determined that information was incomplete or dishonest meaning that a breach by defendant amounted to a waiver of his Fifth Amendment privilege against self-incrimination In addition cooperation agreements explicitly state that all information provided is available to the Court at sentencing and may be considered as either relevant or other conduct when calculating the appropriate Guidelines range and the applicability of departures For the same reason that the Fifth Amendment privilege against self-incrimination survives a guilty plea in that subsequent statements can still adversely affect sentencing exposure statements made subject to a cooperation agreement are against penal interest See Mitchell v United States 526 U S 314 326 1999 w here the sentence has not yet been imposed a defendant may have a legitimate fear of adverse consequences from further 94 Case 15-1815 Document 30 01 12 2016 1682738 Page112 of 170 testimony Undoubtedly then statements made during cooperation may certainly be against the declarant's penal interest The Court's further assessment of Jones's statement - that the chat itself independently and in itself doesn't carry any particular penal impact - improperly fails to consider the context of the statement which implicates Jones in a worldwide criminal conspiracy See Williamson v United States 512 U S 594 603-04 1994 whether a statement is self-inculpatory or not can only be determined by viewing it in context e ven statements that are on their face neutral may actually be against the declarant's interest Also regarding corroboration of the reliability of both the statement and the declarant the Court concluded it was not aware of anything that indicates the trustworthiness of the statements However cooperation agreements provide a compelling even overwhelming motivation for candor because the limited immunity granted is entirely dependent on honest and complete disclosure See United States v Certified Envtl Servs Inc 753 F 3d 72 85-86 2d Cir 2014 cooperation agreements generally contain so-called truth-telling provisions which set out promises to testify truthfully as well as penalties for failure to do so such as prosecution for perjury and reinstatement of any charges dropped pursuant to the deal internal quotations omitted 95 Case 15-1815 Document 30 01 12 2016 1682738 Page113 of 170 Moreover in its December 29 2014 letter informing the defense of Jones's statement the government provided more than sufficient corroboration While the government was unaware of any extant record of the 2013 chat described by Jones t here is a record of an October 2012 chat between DPR and Jones discussing a 'handshake' in the file labeled mbsobzvkhwx4hmjt on the defendant's computer provided to the defense in discovery A398 Thus Jones's statement was more than adequately corroborated for purposes of both Rule 803 4 and Rule 807 requiring equivalent circumstantial guarantees of trustworthiness For that reason and because the government chose mid-trial not to call a cooperating witness who asserted his Fifth Amendment privilege thereby depriving the defense of his testimony and further at the last moment refused to fulfill an agreement to stipulate admission of Jones's statement also satisfied the interests of justice criterion of Rule 807 C as well as the Fifth Amendment Due Process guarantee consistent with Chambers In denying admission of Jones's statement the Court further decimated Ulbricht's defense just as it did with respect to the evidentiary rulings set forth ante in POINTs I II and III Accordingly Jones's statement should have been admitted pursuant to Rule 803 4 and or Rule 807 and the Court abused its discretion in excluding it 96 Case 15-1815 Document 30 01 12 2016 1682738 Page114 of 170 POINT V THE COURT'S ERRONEOUS EVIDENTIARY RULINGS CONSTITUTED CUMULATIVE ERROR THAT DEPRIVED ULBRICHT OF DUE PROCESS AND A FAIR TRIAL While each of the series of evidentiary trial errors set forth above individually are sufficient to warrant vacating Ulbricht's convictions and granting him a new trial cumulatively they require it In combination they served to prevent Ulbricht from presenting any meaningful defense to the charges and permitted the government to argue that the defense theory was unsupported by facts The concept of cumulative error is well established As this Court noted in United States v Al-Moayad 545 F 3d 139 2d Cir 2008 t he Supreme Court has repeatedly recognized that the cumulative effect of a trial court's errors even if they are harmless when considered singly may amount to a violation of due process requiring reversal of a conviction United States v Al-Moayad 545 F 3d 139 178 2d Cir 2008 citing Taylor v Kentucky 436 U S 478 487 n 15 1978 and Chambers v Mississippi 410 U S 284 302-03 1973 Similarly the 'cumulative unfairness' doctrine is also firmly embedded in this Circuit Id citing United States v Guglielmini 384 F 2d 602 607 2d Cir 1967 determining that singly the errors at trial would not require reversal but that occurring at the same trial the total effect of the errors found cast 97 Case 15-1815 Document 30 01 12 2016 1682738 Page115 of 170 such a serious doubt on the fairness of the trial that the convictions must be reversed Accordingly the substantial accumulation of errors as set forth post and ante requires reversal here POINT VI THE UNLIMITED SEARCHES AND SEIZURE OF ULBRICHT'S ENTIRE LAPTOP AND GMAIL AND FACEBOOK ACCOUNTS VIOLATED THE FOURTH AMENDMENT BECAUSE THEY CONSTITUTED THE FRUIT OF A A WARRANT THAT LACKED ANY PARTICULARITY AND B UNLAWFUL AND WARRANTLESS PEN REGISTER AND TRAP AND TRACE ORDERS A The Search of Ulbricht's Laptop and Gmail and Facebook Accounts Violated the Fourth Amendment Because the Warrant Authorizing the Search Lacked Any Particularity As noted ante Ulbricht moved prior to trial to suppress evidence recovered from his laptop seized from him at the time of his arrest and his Facebook and Gmail accounts See Docket#46 The search of Ulbricht's laptop violated the Fourth Amendment because the warrant authorizing the search lacked any particularity but instead expressly and purposefully sought a search without any limiting principle 1 The Unlimited Scope of the Warrants At Issue The warrants here represent the antithesis of particularity not only in execution but also in design language and purpose For example the warrant for 98 Case 15-1815 Document 30 01 12 2016 1682738 Page116 of 170 the laptop sought and received authorization to search for the following with only the most patently offending paragraphs cited herein 44 The SUBJECT COMPUTER is also likely to contain evidence concerning ULBRICHT relevant to the investigation of the SUBJECT OFFENSES including evidence relevant to corroborating the identification of ULBRICHT as the Silk Road user Dread Pirate Roberts including but not limited to a any communications or writings by Ulbricht which may reflect linguistic patterns or idiosyncracies associated with Dread Pirate Roberts or political economic views associated with Dread Pirate Roberts e g views associated with the Mises Institute c any evidence concerning Ulbricht's travel or patterns of movement to allow comparison with patterns of online activity of Dread Pirate Roberts and any information known about his location at particular times h any other evidence implicating ULBRICHT in the SUBJECT OFFENSES S248-49 footnote omitted The deliberate intention to review everything was further manifest from Attachment B to the warrant which included authority to search the laptop for 2 Any evidence concerning ROSS WILLIAM ULBRICHT relevant to the investigation of the SUBJECT OFFENSES including but not limited to a any communications or writings by ULBRICHT c any evidence concerning ULBRICHT'S travel or patterns of movement S252-53 99 Case 15-1815 Document 30 01 12 2016 1682738 Page117 of 170 Moreover the warrants for Ulbricht's gmail and Facebook accounts were similarly without boundaries S311 S383 Thus the entirety of Ulbricht's private papers and more i e his internet history political or other associations were expressly targeted by the government 2 The Court's Rationale for Denying Ulbricht's Motion to Suppress In denying Ulbricht's suppression motions the Court held that the warrants for the laptop and the social media accounts were lawful because they were not general warrants and were supported by probable cause and that pen register and trap and devices did not require a warrant because the type of information sought in Pen-Trap orders 1 2 3 4 and 5 was entirely appropriate for that type of order and t he Pen-Trap Orders do not seek the content of internet communications in any directly relevant sense A201 203-04 3 The Overriding Importance of the Particularity Requirement The critical importance of the particularity requirement in preserving Fourth Amendment rights and protections in the digital age has recently been recognized by this court In United States v Galpin 720 F 3d 436 2d Cir 2013 the Court observed that w here as here the property to be searched is a computer hard drive the particularity requirement assumes even greater importance As numerous courts and commentators have observed advances in 100 Case 15-1815 Document 30 01 12 2016 1682738 Page118 of 170 technology and the centrality of computers in the lives of average people have rendered the computer hard drive akin to a residence in terms of the scope and quantity of private information it may contain Id at 447 citing United States v Payton 573 F 3d 859 861 62 9th Cir 2009 t here is no question that computers are capable of storing immense amounts of information and often contain a great deal of private information Searches of computers therefore often involve a degree of intrusiveness much greater in quantity if not different in kind from searches of other containers other citation omitted footnote omitted See also United States v Otero 563 F 3d 1127 1132 10th Cir 2009 Orin S Kerr Searches and Seizures in a Digital World 119 Harv L Rev 531 569 2005 Indeed last Fall the Court en banc considered the rehearing of the panel's opinion in Ganias United States v Ganias 755 F 3d 125 134 2d Cir 2014 reh'g en banc granted 791 F 3d 290 2d Cir 2015 While the specific issue relative to particularity is distinct herein - not retention and subsequent searching as in Ganias but rather the absence of any particularity in the warrant - the Court's en banc consideration nevertheless underscores the importance of the particularity requirement especially in the context of computers and digital evidence In fact in Ganias and Galpin this Court has twice reversed convictions and suppressed evidence because of violations of the particularity requirement In 101 Case 15-1815 Document 30 01 12 2016 1682738 Page119 of 170 Ganias the panel noted that the particularity requirement makes general searches impossible because it prevents the seizure of one thing under a warrant describing another 755 F 3d at 135 quoting Galpin 720 F 3d at 446 quoting Marron v United States 275 U S 192 196 1927 internal quotation marks omitted That principle restricts the government's ability to remove all of an individual's papers for later examination because it is generally unconstitutional to seize any item not described in the warrant See Horton v California 496 U S 128 140 1990 4 The Warrants At Issue Are Devoid of Particularity Nor is the protest here directed at the initial seizure of a hard drive by imaging it for off-site review The panel opinion in Ganias has already noted that such a procedure is constitutionally permissible 755 F 3d at 135 Rather it is the lack of any limiting standards or procedures during that review Indeed the language cited above from the applications and warrants manifests the opposite intent a detailed review of every piece of digital information In the digital computer context the panel in Ganias recognized that computer files may contain intimate details regarding an individual's thoughts beliefs and lifestyle and they should be similarly guarded against unwarranted Government intrusion If anything even greater protection is warranted Id at 135 citing Kerr Searches and Seizures in a Digital World 119 Harv L Rev at 102 Case 15-1815 Document 30 01 12 2016 1682738 Page120 of 170 569 explaining that computers have become the equivalent of postal services playgrounds jukeboxes dating services movie theaters daily planners shopping malls personal secretaries virtual diaries and more Ganias followed Galpin which explained that the purpose of the particularity requirement is to minimize the discretion of the executing officer 720 F 3d at 446 n 5 and pointed out that m indful of that purpose other Circuits have held that even warrants that identify catchall statutory provisions like the mail fraud or conspiracy statutes may fail to comply with this aspect of the particularization requirement Id citing United States v Leary 846 F 2d 592 594 10th Cir 1988 warrant authorizing search of export company's business records for violation of the Arms Export Control Act 22 U S C 2778 and the Export Administration Act of 1979 50 U S C App 2410 held overbroad Voss v Bergsgaard 774 F 2d 402 10th Cir 1985 warrant specifying 18 U S C 371 the general federal conspiracy statute held overbroad United States v Roche 614 F 2d 6 8 1st Cir 1980 concluding that a limitation of a search to evidence relating to a violation of 18 U S C 1341 the general mail fraud statute provides no limitation at all Also here the language of the governing statutes is not sufficiently precise to provide sufficient particularity indeed general statutes such 21 U S C 841 and 848 are so broad and general that they exacerbate the problem See e g United 103 Case 15-1815 Document 30 01 12 2016 1682738 Page121 of 170 States v Maxwell 920 F 2d 1028 1033 D C Cir 1990 fraud United States v Holzman 871 1496 1509 9th Cir 1989 fraud United States v Fucillo 808 F 2d 173 176-77 1st Cir 1987 See also United States v George 975 F 2d 72 76 2d Cir 1992 Regardless the terms of the warrants imposed no limitation at all on the parameters of the searches In Galpin the Court recounted that it has emphasized that 'a failure to describe the items to be seized with as much particularity as the circumstances reasonably allow offends the Fourth Amendment because there is no assurance that the permitted invasion of a suspect's privacy and property are no more than absolutely necessary ' 720 F 3d at 446 quoting United States v George 975 F 2d 72 76 2d Cir 1992 See also United States v Vilar 2007 WL 1075041 at 22-24 S D N Y Apr 4 2007 suppression granted because warrant inter alia included an omnibus provision permitting seizure of all corporate records In language particularly germane here the Court in Galpin cautioned that t he potential for privacy violations occasioned by an unbridled exploratory search of a hard drive is enormous and that t his threat is compounded by the nature of digital storage 720 F 3d at 446-47 16 See also United States v 16 This Circuit has thus far declined to impose the type of search protocols enumerated by Judge Kozinski in his concurring opinion in United States v Comprehensive Drug Testing Inc 621 F 3d 1162 1176 9th Cir 2010 en banc per curiam However the Court in Galpin recognized 'a serious risk that every warrant for electronic information will become in effect a general warrant rendering the Fourth Amendment irrelevant ' and that t his threat demands 104 Case 15-1815 Document 30 01 12 2016 1682738 Page122 of 170 Abrams 615 F 3d 541 543 1st Cir 1980 warrant failed to satisfy particularity requirement because language was so amorphous that agents' discretion was unfettered In that context the Court in Galpin instructed that upon remand the district court's review of the plain view issue should take into account the degree if any to which digital search protocols target information outside the scope of the valid portion of the warrant To the extent such search methods are used the plain view exception is not available 720 F 3d at 451 Here again no such limiting principles were instituted at all and the warrants inverted the analysis in a manner that dissolves Fourth Amendment protections Rather than require the government to establish probable cause in advance of reviewing categories of electronic data they would license the government to examine every file to assure that probable cause to seize it did not exist Any more dramatic or patent example of the rummaging could not be envisioned yet that is what the government has done in this case with respect to Ulbricht's laptop and Gmail and Facebook accounts 17 a heightened sensitivity to the particularity requirement in the context of digital searches 720 F 3d at 447-48 quoting Comprehensive Drug Testing 621 F 3d at 1176 and citing United States v Burgess 576 F 3d 1078 1091 10th Cir 2009 If the warrant is read to allow a search of all computer records without description or limitation it would not meet the Fourth Amendment's particularity requirement 17 See also Kathleen Ridolfi Tiffany M Joslyn and Todd H Fries Material Indifference How Courts Are Impeding Fair Disclosure In Criminal Cases National 105 Case 15-1815 Document 30 01 12 2016 1682738 Page123 of 170 Nor do the warrants here permit mere perusal to determine relevance as in United States v Mannino 635 F 2d 110 115 2d Cir 1980 quoting United States v Ochs 595 F 2d 1247 1257 n 8 2d Cir 1979 or seek merely a cursory review for purposes of determining relevance as in Andersen v Maryland 427 U S 463 482 n 11 96 S Ct 2737 49 L Ed 2d 627 1976 i n searches for papers it is certain that some innocuous documents will be examined at least cursorily in order to determine whether they are in fact among those papers authorized to be seized Indeed the government announced in the applications that it intended to perform various detailed analyses of the entirety of Ulbricht's communications and digital history That guaranteed that every piece of digital information would be subject to a detailed search in the absence of any probable cause to search any specific piece of electronically stored information Nor is the principle that a warrant can seek and seize mere evidence availing to the government with respect to these warrants See Warden v Hayden 387 U S 294 1967 Warden involved a discrete set of physical objects - clothing and weapons directly related to the offense charged - that were easily Association of Criminal Defense Lawyers and The Veritas Initiative Santa Clara University School of Law November 17 2014 at 12 available at http www nacdl org discovery reform materialindifference e ven if every nook and cranny of a digital device could theoretically contain evidence covered by the warrant it does not mean that every nook and cranny may reasonably contain such evidence emphasis in original 106 Case 15-1815 Document 30 01 12 2016 1682738 Page124 of 170 identifiable not a fishing expedition into the entirety of someone's communications and research history Also in Warden the Court cautioned that t here must of course be a nexus - automatically provided in the case of fruits instrumentalities or contraband - between the item to be seized and criminal behavior in addition to the particularity requirement 387 U S at 300 309-10 Regarding the social media accounts in In the Matter of the Search of Information Associated with Redacted @mac comthat is Stored at Premises Controlled by Apple Inc 13 F Supp 3d 157 D D C August 8 2014 involving a warrant for certain emails the Court emphasized that the particularity requirement ensures that the search will be carefully tailored to its justifications and will not take on the character of the wide-ranging exploratory searches the Framers intended to prohibit Id at 163 In Apple the warrant was sufficiently particularized because it specified in the attachments to its application the particular e-mails to be seized id at 164 and also included a precise temporal limitation Id at 161 No such restrictions on the agents' discretion existed here though See United States v Zemlyansky 945 F Supp 2d 438 457-60 S D N Y 2013 warrant invalid because inter alia it did not sufficiently particularize and failed to impose any temporal limitation on the items to be searched 107 Case 15-1815 Document 30 01 12 2016 1682738 Page125 of 170 Here because the warrants to search Ulbricht's laptop as well as his Gmail and Facebook accounts expressly - even deliberately - fail to adhere to the Fourth Amendment's particularity requirement it is respectfully submitted that all evidence seized and or searched pursuant to those warrants and all the fruits therefrom should be suppressed The Court also questioned whether Ulbricht possessed a legally established personal privacy interest in the laptop and the Google and Facebook accounts without a declaration of his possessory interest in the laptop and the Google and Facebook accounts A183 However not only did the government not contest Ulbricht's standing with respect to those searches but the Court failed to cite any case law for that interpretation Ulbricht was in possession of the laptop at the time of his arrest and there was no factual dispute as to his possession of either the laptop or the Facebook or Google accounts 108 Case 15-1815 Document 30 01 12 2016 1682738 Page126 of 170 B The Pen Register and Trap and Trace Orders Were Unlawful and Violated the Fourth Amendment Because They Required a Warrant and Also Failed to Adhere to Statutory Limitations The Pen Register and Trap and Trace Orders used in this case were implemented by court order and not by a warrant based on probable cause and consequently for the reasons set forth below they violated the Fourth Amendment as well as the statutory framework under which they were obtained Accordingly all evidence acquired as a result of the Pen Registers and Trap and Trace devices and their fruits should have been suppressed and the Court's decision denying Ulbricht's motion was erroneous 1 The Pen Register and Trap and Trace Orders Were Unlawful Because They Required a Warrant The pen register and trap and trace Orders pen-trap at issue herein essentially requested the following this Court has upon the application of the United States of America entered an Order authorizing agents of the Secret Service to direct COMCAST to install a trap and trace device to identify the source Internet protocol IP address of any Internet communications directed to and a pen register to determine the destination IP address of any Internet communications originating from the following Internet user account controlled by COMCAST the TARGET ACCOUNT along with the date time duration and port of transmission but not the contents of such communications the Requested Pen-Trap in connection with a criminal investigation 109 Case 15-1815 Document 30 01 12 2016 1682738 Page127 of 170 S67 18 The pen-trap devices were used on routers IP addresses and MAC addresses 19 See e g S127 Each of the Orders were for 60 days although the full range of surveillance under the pen-trap orders lasted approximately two weeks The applications also claimed the pen-trap devices did not capture content S85 While ostensibly a pen-trap reveals only identifying information these pen-traps had an ulterior purpose to track Ulbricht's internet activity and his physical location in an effort to connect him with access to the administrative section of the Silk Road Servers at particular times on particular dates S245-46 18 According to the applications for the pen-trap Orders a pen register is a device or process which records or decodes dialing routing addressing or signaling information transmitted by an instrument or facility from which a wire or electronic communication is transmitted 18 U S C 3127 3 A trap and trace device is defined as a device or process which captures the incoming electronic or other impulses which identify the originating number or other dialing routing addressing and signaling information reasonably likely to identify the source of a wire or electronic communication 18 U S C 3127 4 S73 19 According to the applications for the pen-trap Orders e very device on the Internet is identified by a unique number called and Internet Protocol 'IP' address This number is used to route information between devices for example between two computers Two computers must know each other's IP addresses to exchange even the smallest amount of information S128-29 A MAC address is a unique identifier that is hard-coded into a computer that can be used to physically identify the computer similar to a vehicle identification number of a car S129-30 110 Case 15-1815 Document 30 01 12 2016 1682738 Page128 of 170 That purpose extends well beyond that permissible for a pen-trap and because the devices were used absent a warrant based on probable cause violates the Fourth Amendment as well as express statutory provisions a Smith v Maryland Does Not Control the Issue Herein In Smith v Maryland 442 U S 735 1979 the Supreme Court held that a telephone subscriber does not have an expectation of privacy in the numbers he or she dials because the subscriber knows full well that the telephone company keeps records of that information which the subscriber has at least tacitly knowingly provided to that third party However the pen-traps in this investigation are not the same as those at issue in Smith and as a result Smith should not control the outcome herein For example in Smith the Court noted in support of its reasoning that a pen register does not indicate whether calls are actually completed Id at 736 n 1 quoting United States v New York Tel Co 434 U S 159 161 n 1 1977 See also id at 741 law enforcement could not even determine from a pen register whether a communication existed Also the Court cited that n either the purport of any communication between the caller and recipient of the call their identities nor whether the call was even completed is disclosed by pen registers 442 U S at 741 quoting United States v New York Tel Co 434 U S at 167 111 Case 15-1815 Document 30 01 12 2016 1682738 Page129 of 170 Here the pen-traps were implemented to do exactly what g iven a pen register's limited capabilities 442 U S at 742 the Supreme Court said the device could not constitutionally do and thus insulated pen-traps from constituting an invasion of private communications The pen-traps here were sought to confirm the laptop's connection to the Internet at specific times and dates their duration and the laptop's physical location when it logged on and off In Smith the Court further based its decision on the fact that pen registers were routinely used by telephone companies 'for the purpose of checking billing operations detecting fraud and preventing violations of law ' 442 U S at 742 quoting New York Tel Co at 174-75 See also id also to check for a defective dial or to check for overbilling citation omitted internal quotation marks omitted Again the Internet provides an entirely different technical and privacy environment than a telephone circuit particularly one in 1979 As explained by Julian Sanchez Research Fellow at the Cato Institute and contributing editor at Reason magazine the Internet functions quite differently from the traditional circuit-switched telephone network On the phone network a binary distinction between content and metadata works well enough The content is what you say to the person on the other end of the call and the metadata is the information you send to the phone company so they can complete the call But the 112 Case 15-1815 Document 30 01 12 2016 1682738 Page130 of 170 Internet is more complicated On the Open Systems Connections model familiar to most techies an Internet communication can be conceptualized as consisting of many distinct layers and a single layer may simultaneously be content relative to the layer below it and metadata relative to the layer above it The crucial point here is that the detailed metadata for a particular Internet communication past the IP layer typically wouldn't be processed or stored by the ISP in the way that phone numbers and other call data is stored by the phone company From the ISP's perspective all of that stuff is content Either way the acquisition of metadata other than IP addresses from an ISP or off the backbone is pretty clearly dissimilar from the collection of call data at issue in Smith in every important respect It is not information conveyed to the Internet provider for the purpose of routing the communication it is routing information conveyed through the provider just like any other content Nor is it information the Internet provider would otherwise normally retain for routine business purposes Again relative to the ISP it's all just content Julian Sanchez Are Internet Backbone Pen Registers Constitutional Just Security September 23 2013 available at http justsecurity org 1042 internet-backbone-pen-registers-constitutional Courts have reached the same conclusion with respect to certain internet information that is captured by a pen-trap particularly that employed here For 113 Case 15-1815 Document 30 01 12 2016 1682738 Page131 of 170 example in United States v Forrester 512 F 3d 500 9th Cir 2007 the Court postulated that s urveillance techniques that enable the government to determine not only the IP addresses that a person accesses but also the uniform resource locators URL of the pages visited might be more constitutionally problematic A URL unlike an IP address identifies the particular document within a website that a person views and thus reveals much more information about the person's Internet activity For instance a surveillance technique that captures IP addresses would show only that a person visited the New York Times' website at http www nytimes com whereas a technique that captures URLs would also divulge the particular articles the person viewed I f the user then enters a search phrase in the Google search engine that search phrase would appear in the URL after the first forward slash This would reveal content Id at 510 n 6 See also In re U S for an Order Authorizing the Use of a Pen Register and Trap on xxx Internet Service Account User Name xxxxxxx@xxx com 396 F Supp 2d 45 49 D Mass 2005 a user may visit the Google site I f the user then enters a search phrase that search phrase would appear in the URL after the first forward slash This would reveal content The substance and meaning of the communication is that the user is conducting a search for information on a particular topic internal quotation marks omitted Indeed even senior government intelligence officials concede that metadata is content See e g Spencer Ackerman NSA Review Panel Casts Doubt On 114 Case 15-1815 Document 30 01 12 2016 1682738 Page132 of 170 Bulk Data Collection Claims The Guardian January 14 2014 available at http www theguardian com world 2014 jan 14 nsa-review-panel-senate-phone-d ata-terrorism quoting former Deputy CIA Director Mike Morrell's testimony before the Senate Judiciary Committee that t here is quite a bit of content in metadata That a privacy expectation in metadata is recognized by society as reasonable is reinforced by the fact that in today's technologically based word it is virtually impossible for an ordinary citizen to avoid creating metadata about himself on a regular basis simply by conducting his ordinary affairs ACLU v Clapper 785 F 3d 787 794 2d Cir 2015 see Klayman v Obama 957 F Supp 2d 1 35-36 D D C 2013 vacated and remanded on other grounds 800 F 3d 559 D C Cir 2015 on remand No CV 13-851 RJL 2015 WL 6873127 D D C Nov 9 2015 the ubiquity of phones has dramatically altered the quantity of information that is now available and more importantly what that information can tell the government about people's lives it is likely that these trends have resulted in a greater expectation of privacy and a recognition that society views that expectation as reasonable emphasis in original See also Clapper 785 F 3d 794 t he more metadata the government collects and analyzes the greater the capacity for such metadata to reveal ever more private and previously unascertainable information about individuals 115 Case 15-1815 Document 30 01 12 2016 1682738 Page133 of 170 Similarly even more recently in United States v Graham 796 F 3d 332 4th Cir 2015 reh'g en banc granted 2015 WL 6531272 4th Cir Oct 28 2015 the Fourth Circuit responding to the government's argument that a third party's possession and even ownership of the defendant's cell site location information CSLI eliminated a defendant's reasonable expectation of privacy rejected the argument that precedents like Smith and United States v Miller 425 U S 435 1976 categorically exclude third-party records from Fourth Amendment protection Id at 354 The Court in Graham explained that e xamination of a person's historical CSLI cell site location information can enable the government to trace the movements of the cellphone and its user across public and private spaces and thereby discover the private activities and personal habits of the user Cellphone users have an objectively reasonable expectation of privacy in this information Its inspection by the government therefore requires a warrant unless an established exception to the warrant requirement applies Id at 345 emphasis added But see United States v Davis 785 F 3d 498 11th Cir 2015 en banc 20 As the Court in Graham declared w e cannot accept the proposition that cell phone users volunteer to convey their location information simply by choosing 20 In Graham the Court nevertheless declined to suppress because the law enforcement agents had relied in good faith on orders rather than warrants issued pursuant to the Stored Communications Act 28 U S C 2703 116 Case 15-1815 Document 30 01 12 2016 1682738 Page134 of 170 to activate and use their cell phones and to carry the devices on their person Id at 356 See also Clapper 785 F 3d at 822-23 rules that permit the government to obtain records and other information that consumers have shared with businesses without a warrant seem much more threatening as the extent of such information grows In re Application of the U S for an Order Authorizing the Release of Historical Cell-Site Info 809 F Supp 2d 113 127 E D N Y 2011 t he fiction that the vast majority of the American population consents to warrantless government access to the records of a significant share of their movements by 'choosing' to carry a cell phone must be rejected More explicitly Justice Sotomayor in concurring in United States v Jones 132 S Ct 945 2012 Sotomayor J concurring challenged the continued vitality of the third-party records doctrine underlying Smith m ore fundamentally it may be necessary to reconsider the premise that an individual has no reasonable expectation of privacy in information voluntarily disclosed to third parties See e g Smith v Maryland 442 U S 735 742 1979 United States v Miller 425 U S 435 443 1976 This approach is ill suited to the digital age in which people reveal a great deal of information about themselves to third parties in the course of carrying out mundane tasks I for one doubt that people would accept without complaint the warrantless disclosure to the Government 117 Case 15-1815 Document 30 01 12 2016 1682738 Page135 of 170 of a list of every Web site they had visited in the last week or month or year Jones 132 S Ct at 957 Sotomayor J concurring Accordingly Smith which describes a primitive methodology that bears little if any resemblance to what the pen-trap devices accomplished in this case does not control the issue herein and the information obtained here through warrantless pen-traps is protected under the Fourth Amendment and falls within the warrant requirement b The Pen-Trap Devices In This Case Required a Warrant Because They Captured Information About Ulbricht's Activities In His Home The pen-trap devices in this case required a warrant because they captured information about Ulbricht's activity within his residence The devices act as a tracking device notifying law enforcement when a target is at home and revealing when and how the target uses his computer at home Thus law enforcement was able to monitor Ulbricht's internet activity while in his home That places pen-trap devices in this case squarely within the jurisprudence of cases such as United States v Karo 468 U S 705 1984 and Kyllo v United States 533 U S 27 2001 In Karo a beeper was used to track the movements of a chemical container to a home and law enforcement continued to monitor the beeper inside the home The Court found that intrusion violate d the Fourth 118 Case 15-1815 Document 30 01 12 2016 1682738 Page136 of 170 Amendment rights of those who have a justifiable interest in the privacy of the residence because it reveal ed a critical fact about the interior of the premises that the government could not have otherwise obtained without a warrant that a particular article is actually located at a particular time in the private residence and is in the possession of the person or persons whose residence is being watched 468 U S at 715 21 Similarly in Kyllo v United States 533 U S 27 2001 the Court again found that the use of technology to reveal information about activity inside a private residence constituted a search under the Fourth Amendment The Court emphasized that w here the Government uses a device that is not in general public use to explore details of the home that would previously have been unknowable without physical intrusion the surveillance is a 'search' and is presumptively unreasonable without a warrant Id at 40 See also Florida v Jardines __ U S __ 133 S Ct 1409 2013 In Graham the Fourth Circuit employed precisely that analogy l ike the searches challenged in Karo and Kyllo examination of historical CSLI can allow 21 In Karo the Court explained that private residences are places in which the individual normally expects privacy free of governmental intrusion not authorized by a warrant and that expectation is plainly one that society is prepared to recognize as justifiable 468 U S at 714 See also id at 716 i ndiscriminate monitoring of property that has been withdrawn from public view would present far too serious a threat to privacy interests in the home to escape entirely some sort of Fourth Amendment oversight Graham 796 F 3d at 346 reh'g en banc granted 2015 WL 6531272 4th Cir Oct 28 2015 119 Case 15-1815 Document 30 01 12 2016 1682738 Page137 of 170 the government to place an individual and her personal property - specifically her cell phone - at the person's home and other private locations at specific points in time 796 F 3d at 346 reh'g en banc granted 2015 WL 6531272 4th Cir Oct 28 2015 State v Earls 214 N J 564 642 2013 Commonwealth v Augustine 467 Mass 230 252-53 2014 c The Pen-Trap Devices In This Case Required a Warrant and or Violated the Operative Statute Because They Captured Prospective Data and Information Another reason the pen-trap devices in this case required a warrant and or violated the operative statute 3127 is because four such orders sought and obtained prospective data and information about Ulbricht's internet activity See e g S66 S77 S92 S124 While there has been a split among courts regarding the propriety of warrantless acquisition of prospective locating information there is ample authority - even a likely majority - for the position that prospective information cannot be obtained absent probable cause while the 3127 orders require only the lower standard of relevance Compare e g In re Order Authorizing Prospective and Continuous Release of Cell Site Location Records 31 F Supp 3d 889 S D Tex 2014 In re Application of the United States for an Order Authorizing the Use of a Pen Register With Caller Identification Device Cell Site Location Authority on a Cellular Telephone 2009 WL 159187 S D N Y Jan 13 2009 120 Case 15-1815 Document 30 01 12 2016 1682738 Page138 of 170 denying application for prospective CSLI In re Application of the United States for an Order Directing a Provider of Electronic Communication Service to Disclose Records to the Government 534 F Supp 2d 585 W D Pa 2008 same In re Application of the United States for an Order Authorizing the Installation and Use of a Pen Register Device 497 F Supp 2d 301 D P R 2007 same with In re Application of the United States for an Order for Disclosure of Telecommunications Records and Authorizing the Use of a Pen Register and Trap and Trace 405 F Supp 2d 435 S D N Y 2005 because location data is imprecise it does not necessarily implicate private space third party doctrine applies to CSLI In re Application of the United States for an Order for Prospective Cell Site Location Information on a Certain Cellular Telephone 460 F Supp 2d 448 S D N Y 2006 In re Application of the United States for an Order Authorizing the Use of a Pen Register and a Trap and Trace Device on Wireless Telephone Bearing Telephone Number Redacted Subscribed to Redacted Service by Redacted No 08 MC 0595 JO 2008 WL 5255815 E D N Y Dec 16 2008 22 2 The Pen Register and Trap and Trace Devices Used In This Case Were Unlawful Because They Exceeded Statutory Authority Moreover the use of the pen-trap devices to establish Ulbricht's internet activity in conjunction with his physical location is the functional equivalent of 22 The cited cases represent a sampling of decisions on both sides of the issue 121 Case 15-1815 Document 30 01 12 2016 1682738 Page139 of 170 geo-locating which could violate the Communications Assistance for Law Enforcement Act CALEA which provides at 47 U S C 1002 a in the context of requiring telecommunications carriers to make their equipment accessible for government electronic surveillance the following caveat with regard to information acquired solely pursuant to the authority for pen registers and trap and trace devices as defined in 18 U S C 3127 such call-identifying information shall not include any information that may disclose the physical location of the subscriber except to the extent that the location may be determined from the telephone number Here the pen-trap Orders were hybrids procured through a combination of authorities - 3127 as well as 18 U S C 2703 d of the Stored Communications Act SCA - and were not authorized exclusively pursuant to 3127 However that resort to the SCA constitutes mere semantics and violates the spirit of CALEA which was designed to foreclose real-time locating as opposed to the SCA which targets historical stored information Indeed such hybrids have been disfavored by a number of courts See e g In re Application 396 F Supp 2d 747 S D Tex 2005 In re Application of U S for Order 497 F Supp 2d 301 302 D Puerto Rico 2007 rejecting application by government for orders under 18 U S C 2703 and 3122 for the installation and use of pen register and trap and trace devices Enhanced Caller 122 Case 15-1815 Document 30 01 12 2016 1682738 Page140 of 170 ID special calling features and the capture of limited geographic or cell site information all for a period of sixty days from the date of the order See also In re Application 2006 WL 1876847 N D Ind July 5 2006 In re Authorizing the Use of a Pen Register 384 F Supp 2d 562 564 on reconsideration sub nom In re Application of the U S for an Order 1 Authorizing the Use of a Pen Register a Trap Trace Device 396 F Supp 2d 294 E D N Y 2005 initial case holds cell site location information which the government seeks is information that a pen register or trap and trace device does by definition provide but it is not information that the government may lawfully obtain absent a showing of probable cause In re Applications of U S for Orders Authorizing Disclosure of Cell Cite Info 05-403 2005 WL 3658531 D D C Oct 26 2005 stating that Magistrate Judges will not grant applications for orders authorizing the disclosure of cell site information pursuant to 18 U S C 2703 18 U S C 3122 and 3123 or both absent new authority and ordering any such applications to be returned to the attorneys Also courts have been unreceptive to applications for pen-traps used for the purpose of ascertaining location See In re U S for an Order 1 Authorizing Installation Use of Pen Register Trap Trace Device 2 Authorizing Release of Subscriber Other Info 3 Authorizing Disclosure of Location-Based Servs No 07-128 2007 WL 3342243 S D Tex Nov 7 2007 AUSA 123 Case 15-1815 Document 30 01 12 2016 1682738 Page141 of 170 request ed an Order authorizing the DEA to require the cell phone Provider to disclose location-based data that will assist law enforcement in determining the location of the Target Device emphasis added prompting Court to conclude that t he information that the Government seeks clearly attempts to identify the exact location of the Target Device and presumably the person holding the Target Device and thus requires a finding of probable cause In re U S For an Order Authorizing the Disclosure of Prospective Cell Site Info 412 F Supp 2d 947 958 E D Wisc 2006 aff'd 06-MISC-004 2006 WL 2871743 E D Wis Oct 6 2006 disagreeing with a prior SDNY case In re Application of the United States of America for an Order for Disclosure of Telecommunications Records and Authorizing the Use of a Pen Register and Trap and Trace 405 F Supp 2d 435 S D N Y 2005 that a pen-trap with some other authority like the SCA could be sufficient to allow for geo-locating and stating that t he bottom line is that the array of statutes invoked by the issues in this case i e the Pen Trap Statute the SCA and CALEA present much more a legislative collage than a legislative mosaic If Congress intended to allow prospective cell site information to be obtained by means of the combined authority of the SCA and the Pen Trap Statute such intent is not at all apparent from the statutes themselves 23 23 In addition the applications for the pen-traps in this case did not reveal to the issuing magistrate judges the true purpose - attempting to ascertain Ulbricht's internet activity in conjunction with his physical location and administrative interaction on the Silk Road Servers - 124 Case 15-1815 Document 30 01 12 2016 1682738 Page142 of 170 POINT VII THE LIFE SENTENCE IMPOSED ON ULBRICHT WAS PROCEDURALLY AND SUBSTANTIVELY UNREASONABLE A The Life Sentence Was Procedurally Unreasonable The life sentence the Court imposed on Ulbricht including the consideration of six alleged overdose deaths as a factor at sentencing was procedurally unreasonable and thereby violated Ulbricht's Fifth Amendment right to Due Process There were two facets to the Court's procedural error 1 the Court erred in fashioning a legal standard not apparently based on any procedural rule or precedent that the deaths in some way related to Silk Road A1472 which required some undefined level of relationship between a criminal defendant and the harm here six deaths in order to attribute that harm to the defendant as relevant conduct at sentencing and 2 even if that vague standard was procedurally reasonable the Court abused its discretion when it based its sentence in part on clearly erroneous facts - the six alleged overdose deaths that the government speculated were the result of drugs purchased on Silk Road and which the Court found by a preponderance of the evidence were in some way related to Silk Road and therefore relevant to Ulbricht's conviction and sentence A1472 See beyond the rudimentary certification that the information sought was relevant to a criminal investigation of Ulbricht See e g S75 at 10 125 Case 15-1815 Document 30 01 12 2016 1682738 Page143 of 170 also United States v Figueroa 647 F 3d 466 469 2d Cir 2011 quoting United States v Cavera 550 F 3d 180 187 2d Cir 2008 en banc stating w e review a criminal sentence for 'unreasonableness ' which 'amounts to review for abuse of discretion' United States v DeSilva 613 F 3d 352 356 2d Cir 2010 holding that p rocedural error includes among other things selecting a sentence based on clearly erroneous facts Accordingly Ulbricht's life sentence should be vacated and he should be remanded to a different judge for resentencing without the alleged overdose deaths as a factor at sentencing 126 Case 15-1815 Document 30 01 12 2016 1682738 Page144 of 170 1 The Court Erred In Considering the Alleged Overdose Deaths Based on An Entirely Subjective Undefined and Unprecedented Standard At sentencing the Court determined there was sufficient factual basis to consider as related conduct relevant to Ulbricht's sentencing six alleged overdose deaths the government claimed resulted from drugs sold through Silk Road A1472 Ulbricht opposed consideration of those accusations and submitted a report by defense expert Mark L Taff M D a Board-certified forensic pathologist that concluded the information was utterly insufficient to attribute any of the deaths to drugs purchased from vendors on Silk Road A904 The government did not present any rebuttal to Dr Taff's report Prior to making its determination the Court stated that a ny factual determinations would be based on the standards set forth in a vast number of cases in the Second Circuit which indicate that such findings are made at sentencing proceedings or in connection with sentencing proceedings by a preponderance of the evidence A1457 The Court then concluded that t he question as to whether this information the six alleged overdose deaths is properly included in the PSR is whether the Court finds by a preponderance of the evidence that the deaths in some way related to Silk Road And they do A1472 Yet while preponderance of the evidence is the established standard of proof for evaluating whether a disputed allegation should be included in the PSR 127 Case 15-1815 Document 30 01 12 2016 1682738 Page145 of 170 the legal standard employed by the Court here- that the deaths in some way related to Silk Road - is not based on any established or cited precedent or procedural rule Nor was it defined or connected to any objective yardstick but rather was hopelessly vague As a result the Court's invented standard does not meet the standard of procedural reasonableness as it creates an entirely vague and subjective basis that defies meaningful consistency or review 2 The Court Improperly Relied on the Alleged Overdose Deaths Purportedly Attributable to the Silk Road Site Without Sufficient or Reliable Proof Moreover even assuming arguendo the validity of the standard employed by the Court the Court nonetheless abused its discretion and violated Ulbricht's Fifth Amendment right to Due Process at sentencing by relying on information regarding the alleged overdose deaths that according to Dr Taff's review of that information was neither reliable nor accurate a The Relevant Case Law It is well-settled that because sentencing is a critical stage in a criminal proceeding a convicted defendant standing before a sentencing judge still remains wrapped in his right to procedural due process and may question the procedure leading to the imposition of his sentence United States v Lee 818 F 2d 1052 128 Case 15-1815 Document 30 01 12 2016 1682738 Page146 of 170 1055 2d Cir 1987 citing Mempa v Rhay 389 U S 128 1967 Gardner v Florida 430 U S 349 358 1977 plurality opinion This Court has held that a lthough the sentencing court has discretion to consider a wide range of information in arriving at an appropriate sentence a defendant may not be sentenced on the basis of materially-untrue statements or on misinformation or misreading of court records United States v Prescott 920 F 2d 139 143 2d Cir 1990 citing Townsend v Burke 334 U S 736 741 1948 United States v Tucker 404 U S 443 446 1972 internal quotations and citations omitted see also United States v Lee 818 F 2d 1052 1055 2d Cir 1987 In order to ensure that a defendant's right to due process at sentencing is meaningful a sentencing court must assure itself that the information upon which it relies when fixing sentence is reliable and accurate Prescott 920 F 2d at 143 citing United States v Pugliese 805 F 2d 1117 1124 2d Cir 1986 see also United States v Fatico 458 F Supp 388 397-398 E D N Y 1978 aff'd in part rev'd in part 603 F 2d 1053 2d Cir 1979 citing United States v Malcolm 432 F 2d 809 816 2d Cir 1970 Accordingly the government shoulders the burden of demonstrating the reliability and accuracy of those facts alleged United States v Fatico 603 F 2d 1053 1057 2d Cir 1979 129 Case 15-1815 Document 30 01 12 2016 1682738 Page147 of 170 b The Court Improperly Relied on Erroneous Facts In Considering the Alleged Overdose Deaths That the Defense Expert Forensic Pathologist Concluded Was Incomplete Unreliable and Inaccurate At Ulbricht's sentencing the Court abused its discretion when it relied on information regarding the alleged overdose deaths that it knew from Dr Taff's Expert Report was incomplete and unreliable Indeed though the Court posited that the question is whether there is a connection between the purchase of the drugs on Silk Road and the death and whether the ingestion of those drugs may be reasonably associated with those deaths and that it c ould make such findings by a preponderance of the evidence and c ould make reasonable inferences the Court also admitted that Dr Taff had identified in his Final Report serious deficiencies in those allegations and serious impediments to relying on them A1476 S437 The Court acknowledged that for each of the six deaths Dr Taff finds in each instance information is missing regarding at least one stage of the six-stage process A1475 The Court also noted the unreliability of the alleged overdose death evidence referring to statements by Dr Taff that in some cases no autopsy was performed and there was no cause of death that could be reliably be determined that without certain pieces of information that were missing from the evidence presented it is impossible for a medical examiner to render 130 Case 15-1815 Document 30 01 12 2016 1682738 Page148 of 170 certain types of opinions and that what are deemed overdoses may be death by suicide or other causes A1476 Likewise the Court noted that based on the quality of the information presented Dr Taff had opine d that he is unable to render opinions to a reasonable degree of medical certainty as to the cause manner and time of death with each of the decedents except for one A1476 Yet the Court summarily dismissed these deficiencies in the information as beside the point claiming that Dr Taff is asking a question which this Court does not need answered despite receiving no contrary evidence or expert analysis from any other source A1476 In fact Dr Taff's analysis establishes not only that the information was unreliable but also that the Court's finding that the information established a connection between the purchase of the drugs on Silk Road and the death s and that ingestion of those drugs may be reasonably associated with those deaths was materially inaccurate A1476 In his Final Report Dr Taff made clear the full range of problems with the government's information stating not only that he was unable to render opinions to a reasonable degree of forensic medical certainty in 5 of 6 cases regarding cause manner and time of death as well as several other forensic issues typically addressed by medical examiners investigating drug-related deaths but also that his inability to render such opinions was due to a paucity of information b 131 Case 15-1815 Document 30 01 12 2016 1682738 Page149 of 170 confusing interpretations selective partial incomplete diagnoses c omissions and d inability to inspect original death investigation and autopsy reports and primary autopsy evidence S445 Indeed even the one death on which Dr Taff was able to provide an opinion he disagreed with the official version of the cause of death because i n his opinion the forensic team failed to factor in the presence of other drugs and a pre-existing heart condition into cause of death A445-46 Further Dr Taff noted that the fact that the decedent's manner of death was classified as an accident indicates that local authorities had insufficient evidence to criminally charge another person for contributing to or directly causing the death Id at A446 Ultimately u nder the clearly erroneous standard of review the question for the reviewing court is whether on the entire record it is left with the definite and firm conviction that a mistake has been committed Sherwin-Williams Co v New York State Teamsters Conference Pension and Retirement Fund 969 F Supp 465 472-473 N D Oh 1997 citing Zenith Radio Corp v Hazeltine Research Inc 395 U S 100 1969 Here given that even the Court acknowledged the shortcomings of the overdose death allegations including that certain critical information was missing the Court clearly erred by nonetheless relying on the unreliable accusations 132 Case 15-1815 Document 30 01 12 2016 1682738 Page150 of 170 Accordingly Ulbricht's sentence should be vacated and the matter remanded for re-sentencing by a different judge untainted by the incurably prejudicial but unsubstantiated and unreliable allegations upon which the Court relied B The Life Sentence Was Substantively Unreasonable In assessing the substantive reasonableness of a sentence the Court looks not only to whether the trial court's decision can be located within the range of permissible decisions but also may consider whether a factor relied on by a sentencing court can bear the weight assigned to it under the totality of circumstances in the case United States v Cavera 550 F 3d 180 189 - 191 2d Cir 2008 internal quotations omitted However while significant deference is afforded the district court's reasoning and ultimate conclusion with respect to sentence several courts including this one have cautioned against converting review for substantive reasonableness into a 'rubber stamp ' United States v Rigas 583 F 3d 108 122 2d Cir 2009 collecting cases see also United States v Rattoballi 452 F 3d 127 137 2d Cir 2006 t o the extent that the district court relied upon the history and characteristics of the defendant on this record those considerations are neither sufficiently compelling nor present to the degree necessary to support the sentence imposed and unjustified reliance upon any one factor is a symptom of an unreasonable sentence 133 Case 15-1815 Document 30 01 12 2016 1682738 Page151 of 170 In particular t he closer a sentence comes to the boundary of the substantively reasonable the more attentive will and should procedural scrutiny be United States v Ingram 721 F 3d 35 45 2d Cir 2013 Calabresi J concurring see also United States v Aldeen 792 F 3d 247 255-56 2d Cir 2015 as amended July 22 2015 remanded for a fuller record because even if the defendant's sentence does not shock the conscience it at the very least stirs the conscience citing United States v Ahuja 936 F 2d 85 89 2d Cir 1991 in cases where the sentence imposed by the district court strains the bounds of reasonableness remand for resentencing may well be warranted Falling squarely in the category of sentences that must be scrutinized carefully and which certainly stir if not shock the conscience is the life sentence imposed here if only because a life sentence is extremely rare in the federal system See e g Glenn R Schmitt Hyun J Konfrst Life Sentences in the Federal System United States Sentencing Commission February 2015 presenting collected national statistics on life sentences imposed in 2013 and noting as of January 2015 only 2 5% of all sentenced federal offenders are serving life sentences available at http www ussc gov sites default files pdf research-and-publications research-pr ojects-and-surveys miscellaneous 20150226_Life_Sentences pdf 134 Case 15-1815 Document 30 01 12 2016 1682738 Page152 of 170 Of all federal offenders sentenced in 2013 only 153 about 0 19% were sentenced to life in prison not including those who received such a lengthy sentence as to be serving a de facto life sentence See Life Sentences Report at 1 Of this minuscule percentage of offenders only 17 about 0 02% of all offenders were subject to a Guidelines range in which life was not the minimum sentence prescribed See id at 9 Specifically with respect to drug trafficking cases the number of offenders sentenced to life drops from 153 to only 64 defendants about 0 08% of all federal offenders and less than 0 33% of all drug trafficking defendants See id at 4 Here the life sentence was substantively unreasonable for several reasons The Court ignored the 99 letters on Ulbricht's behalf that apprised the Court of the positive contributions Ulbricht has made and could make in the future if given a reasonable sentence ignored the expertise of the forensic pathologist and ignored the empirical and other academic and practical research presented in Ulbricht's sentencing submission although some of that research was about Silk Road specifically and its harm reduction effects on the drug culture A904-910 916-18 929 946 951 A1006 Yet the Court instead defaulted to the outdated and now-failed narrative that more incarceration is the solution which courts politicians and policy-makers have affirmatively abandoned A1029-36 A1522-28 The Court relied on unsubstantiated unquantifiable factors that 135 Case 15-1815 Document 30 01 12 2016 1682738 Page153 of 170 necessarily created an unwarranted - and unfair and unreasonable - disparity on a number of levels based on factors that render Ulbricht's sentence unique in its unreasonableness The Court's consideration of the alleged overdose deaths was substantively unreasonable as well as procedurally erroneous In addition to ignoring the expert forensic pathologist the Court penalized Ulbricht in a manner that even those who sell illegal drugs are not The Court did not cite a single case - despite the defense's challenge to the government - in which even those who manage large tangible drug organizations are sentenced based on overdose deaths that are not part of the charges much less any as tenuous and attenuated as those here Indeed in United States v Peter Nash 13 Cr 950 TPG the Honorable Thomas P Griesa sentenced the defendant Peter Nash a k a Samesamebutdifferent a forum moderator and one-time administrator on Silk Road during a time when Silk Road experienced its highest volume of sales to time served - essentially a 14-month sentence See Judgment Docket#36 United States v Peter Nash 13 Cr 950 TPG See Government's Sentencing Submission Nash Sentencing Memo Docket#35 United States v Peter Nash 13 Cr 950 TPG at 4 7-8 Nash pleaded guilty to conspiracy to sell drugs in an amount that made him subject to a ten-year mandatory minimum sentence pursuant to 21 U S C 136 Case 15-1815 Document 30 01 12 2016 1682738 Page154 of 170 841 b 1 A See Nash Sentencing Memo at 4 As a result his base offense level was 36 just like Ulbricht's See id at 5 See also PSR 94 Yet even with multiple downward adjustments for his minor role and his safety valve proffer Nash's adjusted Guidelines range was still 121-151 months See Nash Sentencing Memo at 5 The government did not seek any enhancement for Nash for the deaths cited here although Nash was involved with the site during a period in which five of the six deaths occurred See Nash Sentencing Memo at 4 n 1 In fact Nash's PSR clearly noted the drug-related deaths as the government in its submission remarked that Nash involved himself with the Silk Road site with full knowledge of its activities and with predictably harmful and in some cases deadly consequences as the PSR makes clear Id at 10 24 Yet the Court summarily dismissed that sentence - imposed by a jurist with among the longest current active tenures 24 Two vendors on Silk Road who were the actual sellers of heroin and other drugs - one the leading seller on Silk Road and the other the largest cocaine seller on the site - have been sentenced and were also spared any liability for overdose deaths In fact their sentences were ten years and five years' imprisonment Although they cooperated with the government the disparity between their sentences and Ulbricht's cannot be rationalized by that factor alone See James Cook The Biggest Drug Dealer on Silk Road Has Been Sentenced to 10 Years In Prison Business Insider May 29 2015 available at http www businessinsider com silk-road-drug-dealer-supertrips-sentenced-to-10-years-in-pris on-2015-5 r UK IR T Patrick Howell O'Neill The Dark Net's Cocaine King Just Got 5 Years Behind Bars The Daily Dot March 19 2015 available at http bit ly 1EyGMoN http www dailydot com crime steven-sadler-silk-road-five-years-prison 137 Case 15-1815 Document 30 01 12 2016 1682738 Page155 of 170 In addition to that dramatic disparity Ulbricht did not sell drugs Even assuming his guilt for purposes of sentencing he created an internet platform that enabled others to do so and thus the proper analogy would be to a landlord who knowingly leases space and collects rent and utility payments from tenants whom he knows sell drugs from the premises and even whom he markets to There is a federal statute punishing that conduct - 21 U S C 856 the crack house law - and the maximum sentence is 20 years' imprisonment The Court also created an overwhelming disparity by its reliance on general deterrence which it said plays a particularly important role in this case in part because the Court claimed it was unprecedented A1532-33 Yet the Court again without any contrary authority dismissed all of the literature and studies presented to it on the subject - that general deterrence is illusory and should not be a factor much less used as a basis for a life sentence A1533 Moreover even if general deterrence were a proper factor in this case it did not in any way justify a life sentence but instead created a grotesque disparity The Court did not provide any standard or formula and did not provide any gradation that would make a life sentence as opposed to a term of years appropriate or reasonable For instance at what point does additional imprisonment for purposes of general deterrence lose its effectiveness and become greater than necessary 138 Case 15-1815 Document 30 01 12 2016 1682738 Page156 of 170 Why would a 20-year sentence not provide sufficient deterrence The Court failed to perform any of that analysis See United States v Kim 896 F 2d 678 685 2d Cir 1990 Nor are the Court's assumptions at sentencing about general deterrence borne out by either reality or empirical research The illusory nature of general deterrence clearly holds true for internet drug sales given that they skyrocketed after Ulbricht's arrest and even after his conviction A1027-29 Again even if there were some deterrent effect the Court failed to provide any basis for a life sentence as necessary Resort to general deterrence without any confining principles - some standard some comparative analysis - guarantees that it will create disparity that is immeasurable and inequitable In this case it was also unconscionable The life sentence imposed on 30-year old Ross Ulbricht shocks the conscience - or at the very least stirs it - and is therefore substantively unreasonable Accordingly Ulbricht should be resentenced before a different judge to avoid the irremediable taint from the improper factors the Court considered 139 Case 15-1815 Document 30 01 12 2016 1682738 Page157 of 170 Conclusion Accordingly for all the reasons set forth above it is respectfully submitted that Ulbricht's conviction should be vacated and or evidence derived from invalid warrants and pen trap orders should be suppressed and or Ulbricht should be remanded for resentencing before a different judge Dated 12 January 2016 New York New York Respectfully submitted S Joshua L Dratel JOSHUA L DRATEL JOSHUA L DRATEL P C 29 Broadway Suite 1412 New York New York 10006 212 732-0707 Attorneys for Defendant Ross Ulbricht - Of Counsel - Joshua L Dratel Lindsay A Lewis Whitney G Schlimbach Joshua J Horowitz 140 Case 15-1815 Document 30 01 12 2016 1682738 Page158 of 170 CERTIFICATE OF COMPLIANCE WITH FRAP 32 a 1 This brief complies with the type-volume limitation of Fed R App P 32 a 7 B because this brief contains 30 182 words excluding the parts of the brief exempted by Fed R App P 32 a 7 B iii 2 This brief complies with the typeface requirements of Fed R App P 32 a 5 and the type style requirements of Fed R App P 32 a 6 because this brief has been prepared in a proportionally spaced typeface using Microsoft Word in Times New Roman 14 point font Respectfully submitted S Joshua L Dratel JOSHUA L DRATEL JOSHUA L DRATEL P C 29 Broadway Suite 1412 New York New York 10006 212 732-0707 Attorneys for Defendant Ross Ulbricht Case 15-1815 Document 30 01 12 2016 1682738 Pag9159 of 170 SPECIAL APPENDIX Case 15-1815 Document 30 01 12 2016 1682738 Page160 of 170 Table of Contents Page Judgment of the United States District Court Southern District of New York entered May 29 2015 Appealed From SPA1 Notice of Appeal entered June 4 2015 SPA10 SPA1 Case 15-1815 Document 30 01 12 2016 1682738 Page161 of 170 Case 1 14-cr-00068-KBF Filed 06 01 15 Document 269 Page 1 of 9 Rev 09111 Judgment in a Criminal Case Sheet I AO 245B UNITED STATES DISTRICT COURT Southern District of New York UNITED STATES OF AMERICA v JUDGMENT IN A CRIMINAL CASE Ross William Ulbricht Case Number S1 14-cr-00068-KBF-1 USMNumber 18870-111 Joshua Dratel Defendant's Attorney THE DEFENDANT o pleaded guilty to count s o pleaded nolo contendere to count s which was accepted by the court i was found guilty on count s after a plea of not guilty 2 4 5 6 7 -------------------------------------------------------------------- The defendant is adjudicated guilty of these offenses Title Section Nature of Offense Offense Ended 21 841A CD F AIDING AND ABETTING DISTRIBUTION 21 848 F CONTINUING 18 1030A F COMPUTER HACKING CONSPIRACY CRIMINAL ENTERPRISE The defendant is sentenced as provided in pages 2 through the Sentencing Reform Act of 1984 o The defendant i Count s OF DRUGS aVE __ 9 of this judgment 10 31 2013 2 10 31 2013 4 10 31 2013 5 The sentence is imposed pursuant to has been found not guilty on count s 0 UNDERLYING is are dismissed on the motion of the United States It is ordered that the defendant must notify the United States attorney for this district within 30 days of any change of name residence or mail ing address until all fines restitution costs and special assessments imposed by this judgment are fully paid If ordered to pay restitution the defendant must notify the court and United States attorney of material changes in economic circumstances 5 29 2015 Counts One 1 and Three 3 are vacated by Date of Imposition of Judgment the Court Signature of Judge USDCSDNY DOCUMENT ELECTRONICALLY DOC # UN DATE FILEd Katherine B Forrest USDJ FILED 0 1 2015 Name and Title of Judge Date G 5 11111 ---------- SPA2 Case 15-1815 Document 30 01 12 2016 1682738 Page162 of 170 Case 1 14-cr-00068-KBF AO 24513 Document 269 Filed 06 01 15 Page 2 of 9 Rev 09 11 Judgment in a Criminal Case Sheet I A Judgment-Page _ _ of DEFENDANT Ross William Ulbricht CASE NUMBER S1 14-cr-00068-KBF-1 ADDITIONAL COUNTS OF CONVICTION Title Section Nature of Offense Offense Ended 18 1028A F FRAUD WITH IDENTIFICATION 18 1956-4999 F MONEY LAUNDERING CONSPIRACY DOCUMENTS 1111 Count 10 31 2013 6 10 31 2013 7 _ SPA3 Case 15-1815 Document 30 01 12 2016 1682738 Page163 of 170 Case 1 14-cr-00068-KBF AO 2458 Document 269 Filed 06 01 15 Page 3 of 9 Rev 09 11 Judgment in Criminal Case Sheet 2 Imprisonment Judgment Page 3 of 9 DEFENDANT Ross William Ulbricht CASE NUMBER S1 14-cr-00068-KBF-1 IMPRISONMENT The defendant is hereby committed to the custody of the United States Bureau of Prisons to be imprisoned for a total term of Counts Two 2 and Four 4 Life to run concurrently Count 5 Five 5 Years to run concurrently Count Six 6 Fifteen 15 Years to run concurrently Count Seven 7 Twenty 20 Years to run concurrently ilf The court makes the following recommendations to the Bureau of Prisons PLEASE SEE ADDITIONAL IMPRISONMENT TERMS PAGE FOR RECOMMENDATIONS o The defendant is remanded to the custody of the United States Marshal o The defendant shall surrender to the United States Marshal for this district o o o o at a m o p m on as notified by the United States Marshal The defendant shall surrender for service of sentence at the institution designated by the Bureau of Prisons o o as notified by the United States Marshal o as notified by the Probation or Pretrial Services Office before 2 p m on RETURN I have executed this judgment as follows Defendant delivered on a ___ to _ _ with a certified copy of this judgment UNITED STATES MARSHAL By DEPUTY UNITED STATES MARSHAL 11 __ SPA4 Case 15-1815 Document 30 01 12 2016 1682738 Page164 of 170 Case 1 14-cr-00068-KBF AO 2458 Document 269 Filed 06 01 15 Page 4 of 9 Rev 09111 Judgment in a Criminal Case Sheet 2A - Imprisonment Judgment-Page DEFENDANT Ross William Ulbricht CASE NUMBER 81 14-cr-00068-KBF-1 ADDITIONAL IMPRISONMENT TERMS It is respectfully recommended that the defendant be designated to FCI Petersburg I in Virginia in the event that the Bureau of Prisons waive the public safety factor with regard to sentence length However if the Bureau of Prisons is not inclined to waive the public safety factor it is respectfully recommended that the defendant be designated to U8P Tuscon in Arizona or as a second choice U8P Coleman II in Florida 111111111111111 _ SPA5 Case 15-1815 Document 30 01 12 2016 1682738 Page165 of 170 Case 1 14-cr-00068-KBF AO 245B Document 269 Filed 06 01 15 Page 5 of 9 Rev 09111 Judgment in a Criminal Case Sheet 3 - Supervised Release Judgment-Page of DEFENDANT Ross William Ulbricht CASE NUMBER S1 14-cr-00068-KBF-1 SUPERVISED RELEASE Upon release from imprisonment the defendant shall be on supervised release for a term of Life on Counts Two 2 and Four 4 to run concurrently Three 3 Years on Counts Five 5 Six 6 and Seven 7 to run concurrently The defendant must report to the probation office in the district to which the defendant is released within 72 hours of release from the custody of the Bureau of Prisons The defendant shall not commit another federal state or local crime The defendant shall not unlawfully possess a controlled substance The defendant shall refrain from any unlawful use of a controlled substance The defendant shall submit to one drug test within 15 days of release from imprisonment ana at least two periodic drug tests thereafter as determined by the court The above drug testing condition is suspended based on the court's determination that the defendant poses a low risk of future substance abuse Check if applicable The defendant shall not possess a firearm ammunition destructive device or any other dangerous weapon The defendant shall cooperate in the collection of ON A as directed by the probation officer Check if applicable Check if applicable o The defendant shall comply with the requirements of the Sex Offender Registration and Notification Act 42 U S c 1690 I et seq as directed by the probation officer the Bureau Prisons or any state sex offender registration agency in which he or she resides works IS a student or was convicted of a qualifying offense Check if applicable o The defendant shall participate in an approved program for domestic violence or Check if applicable If this judgment imposes a fine or restitution it is a condition of supervised release that the defendant pay in accordance with the Schedu Ie of Payments sheet of th is judgment The defendant must comply with the standard conditions that have been adopted by this court as well as with any additional conditions on the attached page STANDARD CONDITIONS OF SUPERVISION I the defendant shall not leave the judicial district without the permission of the court or probation officer 2 the defendant shall report to the probation officer in a manner and frequency directed by the court or probation officer 3 the defendant shall answer truthfully all inquiries by the probation officer and follow the instructions of the probation officer 4 the defendant shall support his or her dependents and meet other family responsibilities 5 the defendant shall work regularly at a lawful occupation unless excused by the probation officer for schooling training or other acceptable reasons 6 the defendant shall notify the probation officer at least ten days prior to any change in residence or employment 7 the defendant shall refrain from excessive use of alcohol and shall not purchase possess use distribute or administer any controlled substance or any paraphernalia related to any controlled substances except as prescribed by a physician 8 the defendant shall not frequent places where controlled substances are illegally sold used distributed or administered 9 the defendant shall not associate with any persons engaged in criminal activity and shall not associate with any person convicted of a felony unless granted permission to do so by the probation officer 10 the defendant shall permit a probation officer to visit him or her at any time at home or elsewhere and shall permit confiscation of any contraband observed in plain view of the probation officer 11 the defendant shall notify the probation officer within seventy-two hours of being arrested or questioned by a law enforcement officer 12 the defendant shall not enter into any agreement to act as an informer or a special agent of a law enforcement agency without the permission of the court and 13 as directed by the probation officer the defendant shall notify third parties of risks that may be occasioned by the defendant's criminal record or Personal history or characteristics and shall permit the probation officer to make such notifications and to confirm the defendant s compliance with such notification requirement SPA6 Case 15-1815 Document 30 01 12 2016 1682738 Page166 of 170 Case 1 14-cr-00068-KBF AO 245B Document 269 Filed 06 01 15 Page 6 of 9 Rev 09 11 Judgment in a Criminal Case Sheet 3A - Supervised Release JUdgment-Page of DEFENDANT Ross William Ulbricht CASE NUMBER S1 14-cr-00068-KBF-1 ADDITIONAL SUPERVISED RELEASE TERMS The defendant shall submit his computer person and place of residence to searched as deemed appropriate by the Probation Department SPA7 Case 15-1815 Document 30 01 12 2016 1682738 Page167 of 170 AO 245B Rev 09 11 JQ lak1liii faIQQQ68-KBF Document 269 Filed 06 01 15 Page 7 of 9 Sheet 5 - Criminal Monetary Penalties Judgment - Page of DEFENDANT Ross William Ulbricht CASE NUMBER S1 14-cr-00068-KBF-1 CRIMINAL MONETARY PENALTIES The defendant must pay the total criminal monetary penalties under the schedule of payments on Sheet 6 Assessment $ 500 00 TOTALS o o Restitution $ The determination of restitution is deferred until after such determination $ An Amended Judgment in a Criminal Case AG 245C will be entered --- The defendant must make restitution including community restitution to the following payees in the amount listed below lfthe defendant makes a partial payment each payee shall receive an approximately proportioned J ayment unless specified otherwise in the priority order or percentage payment column below However pursuant to 18 U s C 36640 all nonfederal victims must be paid before the United States is paid Name of Payee TOTALS o o o Total Loss 0 00 $ Restitution amount ordered pursuant to plea agreement Restitution Ordered Priority or Percentage 0 00 $ $ The defendant must pay interest on restitution and a fine of more than $2 500 unless the restitution or fine is paid in full before the fifteenth day after the date of the judgment pursuant to 18 U S C 3612 1 All of the payment options on Sheet 6 may be subject to penalties for delinquency and default pursuant to 18 U S c 3612 g The court determined that the defendant does not have the ability to pay interest and it is ordered that o o the interest requirement is waived for the the interest requirement for the 0 fine 0 0 fine 0 restitution restitution is modified as follows Findings for the total amount oflosses are required under Chapters I09A 110 II OA and 113A of Title 18 for offenses committed on or after September 13 1994 but before April 23 1996 I ---------------------- SPA8 Case 15-1815 Document 30 01 12 2016 1682738 Page168 of 170 AO 2458 Rev 09 11 G Il rQ'iiQQQp8-KBF Document 269 Filed 06 01 15 Page 8 of 9 Sheet SA - Criminal Monetary Penalties Judgment-Page 8 of 9__ DEFENDANT Ross William Ulbricht CASE NUMBER S1 14-cr-00068-KBF-1 ADDITIONAL TERMS FOR CRIMINAL MONETARY PENALTIES Forfeiture in the amount of $183 961 921 00 is Ordered -------------------- SPA9 Case 15-1815 Document 30 01 12 2016 1682738 Page169 of 170 AO 2458 Rev 09 1 I JQ GBPQ ilil14rr Wf I1 QQ68-KBF Document 269 Filed 06 01 15 Page 9 of 9 Sheet 6 - Schedule of Payments Judgment - Page 9 of 9 DEFENDANT Ross William Ulbricht CASE NUMBER 81 14-cr-00068-KBF-1 SCHEDULE OF PAYMENTS Having assessed the defendant's ability to pay payment of the total criminal monetary penalties is due as follows A Lump sum payment of $ D D not later than in accordance 500 00 D C due immediately balance due D D D or E or B D Payment to begin immediately may be combined with C D Payment in equal _ __ __ D '_'__ D F below or DC D D or D F below or e g weekly monthly quarterly installments of $ over a period of e g months or years to commence e g 30 or 60 days after the date of this judgment or D Payment in equal _________ __ e g weekly monthly quarterly installments of $ over a period of e g months or years to commence e g 30 or 60 days after release from imprisonment to a term of supervision or E D Payment during the term of supervised release will commence within F D Special instructions regarding the payment of criminal monetary penalties e g 30 or 60 days after release from imprisonment The court will set the payment plan based on an assessment of the defendant's ability to pay at that time or Unless the court has expressly ordered otherwise ifthisjudgment imposes imprisonment payment of criminal monetary penalties is due during imprisonment All cnminal monetary penalties except those payments made through the Federal Bureau of Pnsons' Inmate Financial Responsibility Program are made to the clerk of the court The defendant shall receive credit for all payments previously made toward any criminal monetary penalties imposed D Joint and Several Defendant and Co-Defendant Names and Case Numbers including defendant number Total Amount Joint and Several Amount and corresponding payee if appropriate o The defendant shall pay the cost of prosecution D The defendant shall pay the following court cost s D The defendant shall forfeit the defendant's interest in the following property to the United States Payments shall be applied in the following order 1 assessment 2 restitution principal 3 restitution interest 4 fine principal 5 fine interest 6 community restitution 7 penalties and 8 costs including cost of prosecution and court costs SPA10 Case 15-1815 Document 30 01 12 2016 1682738 Page170 of 170 Case 1 14-cr-00068-KBF Filed 06 04 15 Document 274 c sn ' N Y r I Criminal Notice of Appeal - Form A NOTICE OF APPEAL Page 1 of 1 United States District Court _S_o_u_th_e_r_n District of New_Y_o_r_k DOCUMENT ELECTRONiCALLY FILED ' '- _ _ o - - v Docket No 14 Cr 68 KBF Honorable Katherine B Forrest District Court Judge Ross William Ulbricht Notice is hereby given that Ross William Ulbricht Appeals for the Second Circuit from the judgment f appeals to the United States Court of ___ J other l f and PreliminaryOrderof Forfeiture Money Judgment specify entered in this action on June 1 2015 date This appeal concerns Conviction only l__ Sentence only L_j Defendantfound guilty by plea I I N A I I triall f Offense occurred after November 1 1987 Yes I f i Date of sentence _M_a_y_2_9_ _2_O_15 Bail Jail Disposition Committed I f No IN A Conviction Sentence f Other L___ N A L_j Not committed I Appellant is represented by counsel Yes f I No I I N A I I If yes provide the following information Defendant's Counsel Law Offices of Joshua L Dratel Counsel's Address 29 Broadway Suite 1412 P C New York New York 10006 Counsel's Phone 212 732-0707 Assistant U S Attorney Serrin Turner AUSA's Address United States Attorney's Office Southern District of New York One Saint Andrews AUSA's Phone II I i g iE# 1LED cIUN '015 1 Caption United States --11 Plaza New York New York 10007 212-637-1946 L AZF--Signature j                     National Security Archive    Suite 701  Gelman Library  The George Washington University    2130 H Street  NW  Washington  D C  20037    Phone  202 994‐7000  Fax  202 994‐7005  nsarchiv@gwu edu