astute use of its famous cigars as creative diplomatic tools   Indeed throughout the more than half a century of acrimony hostility and aggression in U S –Cuban relations Cuba has repeatedly practiced the art of “cigar diplomacy ” providing its world-class tobacco products—more often than not Fidel’s favorite Cohiba Lanceros—as a peace offering to open dialogue toward more normal ties with the United States CHE THE FIRST CIGAR DIPLOMAT Fidel Castro’s first attempt at cigar diplomacy came in the aftermath of the infamous Bay of Pigs invasion Only four months after the failed CIA-led paramilitary attack Castro sent his revolutionary deputy Ernesto ‘Che’ Guevara to the Alliance for Progress summit in Uruguay knowing that representatives of the Kennedy administration would be attending   From 116 top left AP Photo bottom left AP Photo Phil Sandlin right Hank Walker The LIFE Picture Collection Getty Images During the 1980 Mariel boatlift top relatives of Cuban refugees line the dock in Key West Florida as another boat docks at U S Customs Cuban refugees bottom await processing White House aide Richard Goodwin right conducted secret talks with Che Guevara in the early 1960s the other side of the conference room Guevara observed a young White House aide Richard Goodwin smoking a cigar and decided to break the ice with a diplomatic dare He sent an Argentine diplomat named Horacio Rodríguez Larreta across the room to convey this Cold War challenge “I bet you wouldn’t smoke Cuban cigars ” In an interview with the authors Goodwin recalled his response “I said ‘Hell I’d smoke them in a minute but I can’t get them at home anymore ’ Next day in my room there was a box of Cuban cigars with a handwritten note from Che Guevara ” The cigars were encased in an ornate mahogany box inlaid with the seal of the Republic of Cuba the note made it clear that they were intended not for Goodwin but rather for the President of the United States In Cuba’s first serious act of diplomacy to move relations forward Guevara’s note stated simply “To write to the enemy is difficult I limit myself to extending my hand ” At an impromptu all-night meeting in Montevideo Guevara did just that approaching Goodwin at a party and inviting him sit down in a private room  to talk candidly about the future of U S –Cuban relations When Guevara sat on the floor Goodwin did the same “I was not going to let him out prolitarianize me ” Goodwin would later declare As the room filled  with cigar smoke their conversation lasted “until dawn had lighted the Montevideo skies ” Goodwin recalled as they shared perspectives on overcoming the hostile state of relations   Guevara thanked Goodwin for the Bay of Pigs which he said had enabled Castro to consolidate the revolution and “transformed them from an aggrieved little country to an equal ”  Now empowered as an equal Guevara made it clear that Cuba sought a peaceful coexistence with the United States and was willing to negotiate on key issues—expropriated properties Cuban support for revolution in Latin America among them—to advance that goal “They would like a modus vivendi ” Goodwin recorded in a secret memorandum of this historic conversation When Goodwin returned to Washington he went directly to the White House to brief Kennedy and give him Guevara’s gift box of cigars Kennedy “opened them and he says ‘Are they good ’ And I said ‘Good Mr President No they are the best ’ where upon he immediately took one out of the box bit off the end and lit it up ” as Goodwin recalled the scene “You should have smoked the first one ” the President joked in an oblique acknowledgement that cigars could be used to assassinate heads of state  As Goodwin recalled their conversation “I said ‘Too late now Mr President ’” Neither Castro’s cigar diplomacy nor Guevara’s proposals to negotiate a peaceful co-existence between Washington and Havana produced immediate results Goodwin recommended to Kennedy that the administration “seek some way of continuing the below-ground dialogue that Che has begun ” and even tasked the CIA to develop a “precise covert procedure” through which talks could be quietly pursued but for the next year Kennedy ignored Cuba’s overture Instead he deferred to the hawks in his administration who continued to focus on overthrowing Castro and rolling back the Cuban revolution Only in the aftermath of the Cuban missile crisis which brought the world to the brink of nuclear war did the White House resurrect the concept of a “below-ground dialogue” with Cuba During the last months of his tragically abbreviated administration Kennedy pursued secret diplomatic talks with Castro toward a potential rapprochement using a series of intermediaries including a French journalist named Jean Daniel On November 22 1963 at the very moment the President was assassinated in Dallas Daniel was in Cuba sharing with Castro a message of reconciliation that Kennedy had personally asked him to deliver “This is an end to your mission of peace ” Castro exclaimed as they listened to the shocking news on radio “This is an end to your mission… ” his chosen courier Democratic Party operative Frank Mankiewicz Mankiewicz traveled to Cuba with two colleagues Saul Landau and Kirby Jones to do a television interview with Castro and personally handed him Kissinger’s note   “This is a very serious communication and we will of course consider it very carefully ” Castro told the group after reading the message in his study Before they returned Castro gave Mankiewicz a handwritten response for Kissinger agreeing to undertake a series of secret meetings between their respective representatives To punctuate his willingness to engage in a secret dialogue with KISSINGER’S CUBA DÉTENTE Another decade would pass before the two countries reengaged in serious and very secretive talks toward normal relations This time the initiative was undertaken by Secretary of State Henry Kissinger Once again Castro used cigars to help the dialogue get off to a promising start Kissinger faced a diplomatic conundrum over U S policy toward Cuba At home there was growing pressure in the U S Congress to lift the trade embargo including from Senators and Congressmen who relished a good Cuban cigar Abroad Washington’s efforts to isolate Castro in Latin America were now isolating the United States instead One Envoys carried Secretary of State Henry Kissinger’s note to Castro and came home with by one Latin American nations were breaking with the cigars Left to right Frank Mankiewicz Saul Landau Fidel Castro and Kirby Jones multilateral embargo that the OAS under U S pressure had Washington Castro gave Mankiewicz Jones and Landau a special box of passed in 1964 banning economic and diplomatic ties with Cuba In the Cohibas “This is a box for Henry Kissinger ” he told them Since travel summer of 1974 the OAS had scheduled a vote to lift the multilateral between Havana and Miami was prohibited at the time Castro provided sanctions which would finally be lifted in 1975 “We have a poor hand his private plane to fly them to Nassau so that they could more quickly to play and should ask for a new deal before we lose our last chip ” one aide travel to the States and give Kissinger both his note and the cigars But in Nassau Castro’s effort at cigar diplomacy was almost thwarted “This is a very serious by a disciplined Custom’s officer   “We had 12 boxes of cigars ” Kirby Jones communication and we will recalled “And they did not fit in the luggage We decided just to carry them ” When the Customs agent noticed what they were carrying he said of course consider it very “Oh my god what do we have here ” As the agent threatened to confiscarefully ” said Fidel Castro cate all of the cigars as contraband Mankiewicz stood up for cigar diploHe backed up his will to talk macy   “Son ” he recalled telling the young agent “this box of cigars is a personal gift for Secretary of State Henry Kissinger Are you sure you want with a gift—a box of cigars to take them away ” Mankiewicz prevailed “If you guys are crazy enough to think you can get these in to Kissinger ” the Customs officer told warned Kissinger in a classified memorandum on the need to negotiate them as he relented “you deserve to take them ” Mankiewicz completed with Castro before the OAS vote his mission delivering the cigars to the Secretary of State The Secretary of State agreed Kissinger decided to make a virtue out So began the most serious diplomatic effort to normalize relations of necessity and use these diplomatic circumstances as an opportunity for since Washington broke ties with Havana in January 1961 Over the next an historic accord with Cuba In late June of 1974 he sent a secret 18 months Kissinger and Castro’s emissaries traveled back and forth handwritten note to the Cuban leader   Kissinger’s message—unsigned between Washington and Havana holding furtive meetings in lounges at in order to maintain plausible denial if it leaked—stated that he was La Guardia and National airport the private homes of U S officials and anxious to discuss bilateral issues and hoped “to find a way to communieven the swanky Pierre Hotel in New York City to address the issues that cate ” Such discussions needed to be conducted discretely using intermehad divided the two countries since the 1959 revolution “It is better to diaries   “This is the way I did it with Chou En-lai ” Kissinger informed 119 government to normalize migration improve military-to-military relations establish U S media bureaus in Havana and establish counter-terrorism and counternarcotics cooperation Toward the end of Clinton’s first term   Fidel Castro’s personal effort to arrange a unique exchange— political prisoners for a presidential guarantee of halting hostile incursions of Cuban airspace—led to one of the stranger episodes of cigar diplomacy in the annals of U S –Cuban relations In late 1994 an organization of Cuban-American pilots known as Brothers to the Rescue BTTR led by a veteran anti-Castro exile named José Basulto began overflying Havana and raining down bumper stickers propaganda leaflets and religious trinkets on the city “We want confrontation ” Basulto declared after one incursion of Cuban airspace His penetration of Cuban airspace served “as a message to the Cuban people ” CLINTON’S CONTRABAND COHIBAS he boasted “The regime is not invulnerable ” For a country with a long history of exile terrorism including bombs The Carter administration attempted to pick up on the Kissinger initiadropped from small airplanes on the countryside these overflights were tive and made significant early gains in establishing at least partial diplonot only a violation of Cuban sovereignty the Cubans perceived them as matic relations through the creation of “Interest Sections” in Havana and a serious threat to national security The Castro government used every Washington that functioned like Embassies But the administration deavailable channel of communication—formal diplomatic notes official manded that Castro get his troops out of Africa before the embargo could letters to the FAA direct phone calls to the State Department and a be lifted and relations fully normalized Castro’s attempt in the fall of stream of messages sent through intermediaries to the White House—to make it clear to the Clinton administration that the BTTR flights would not be tolerated and to press the White House to clip Basulto’s wings and halt his flights A then little-known Congressman from New Mexico named Bill Richardson became the key intermediary Castro used to convey this message to Clinton On January 17 1996 just four days after Basulto dropped a half million leaflets over the Cuban capital exhorting the Cuban people to “Change Things Now ” Richardson arrived in Havana to lobby for the release of a group of political prisoners Castro offered a quid pro quo Richardson “should go back to Washington and get an assurance from Clinton that the flights would be stopped ” Then Castro would release several prisoners in return   To underscore the importance of this mission Castro gave Richardson a special box of Cohibas as a gift to the President of the United States When Richardson returned to Washington he contacted the White House and received assurances from an official there that the FAA had been instructed to ground Basulto and his José Basulto the president of Brothers to the Rescue triggered a major diplomatic BTTR flights He also called Richard Nuccio the Special Adviincident between Cuba and the United States by sending private flights over Cuba sor to the President and Secretary of State for Cuban Affairs and asked him to come to Richardson’s Capitol Hill office   “He reached under 1980 to help Jimmy Carter’s chances for reelection by ending the Mariel his desk and pulled out a duffle bag full of cigars ” Giving Nuccio a box boatlift—and to curry favor with Secretary of State Muskie with a diplohe said “Get this to the president ” Nuccio recounted in an interview matic gesture of 100 premium cigars—proved to be too little and too late with the authors There would be no second term for  Carter—he lost to Ronald Reagan in Nuccio took the box directly to the West Wing office of National a landslide—no second chance to pursue normalizing relations with Security Advisor Samuel Berger “I have a box of cigars A personal gift Cuba “I think in retrospect knowing what I know since I left the White from President Castro to president Clinton ” Nuccio told him “Would House ” the former president later admitted in an interview with the auyou like to give it to him ” thors “I should have gone ahead and been more flexible in dealing with In an election year in which Florida would be a swing state Berger Cuba and established full diplomatic relations ” understood the potential political implications of Clinton receiving Neither Ronald Reagan nor the administration of George H W Bush banned Cuban cigars from Fidel Castro “Those cigars will never get to offered much opportunity for cigar diplomacy with Cuba But Bill Clinton the president ” he sternly instructed Nuccio “The president will never was known to love a good Cuban cigar The Clinton administration know you have those cigars They are leaving this office right now and engaged in a series of open and back-channel talks with the Cuban 122 Alan Diaz Getty Images deal straight with Castro ” Kissinger instructed his deputies “Behave chivalrously do it like a big guy not like a shyster ” But despite serious intentions the Kissinger initiative to bring détente to the Caribbean eventually failed Castro’s audacious decision in 1975 to dispatch 36 000 Cuban troops to Africa to fend off a CIAsupported South African invasion of Angola dramatically narrowed the political latitude for the Republican administration of Gerald Ford to pursue better relations with Havana Indeed as the 1976 Presidential election year evolved President Ford tacked rightward on improved relations and  Kissinger himself went from pursuing secret diplomacy designed to arrive at an  accommodation with Castro to ordering contingency plans to as he told the President “clobber the pipsqueak ” going back to your office and going right into the safe   And if I ever hear that the president knows that there are cigars for him I’ll know where he got that information ” But the saga of Castro’s attempt at cigar diplomacy with President Clinton did not end there Concerned about protocol Berger filed a report with the White House Secret Service that the illicit cigars should be officially confiscated and destroyed Nuccio recalled what happened next “These security guys would show up and say ‘Sir we’re here to confiscate the Cuban contraband’ and I would say There’s no Cuban contraband This was brought in by a member of Congress and it needs to be preserved ’ The officials would respond   “ ‘Well alright sir but we’ll get back to you about this ’ ” After several such visits a team of Secret Service agents arrived at Nuccio’s office and informed him that they had specific orders “to destroy the Cuban contraband” and demanded that he turn over the cigars “We went to the men’s room and they went into a stall and crumpled every cigar into the toilet and flushed them down the toilet ” Nuccio recalled ruefully   The agents also tore up the cedar box the cigars had been in and tossed it in the trash All that remained of Castro’s gift was a band from one of the Cohibas that Nuccio asked to keep “so I could prove this story ” Sad as it was the fate of the presidential Cohibas paled in comparison to the human and political tragedy that followed When he returned to Cuba in early February 1996 to take three political prisoners back to the U S Richardson left Castro with the incorrect impression that Clinton had personally ordered the BTTR flights to be halted Indeed Castro informed his top aides that he “had a clear commitment from one head of state to another that the flights would be stopped ” Yet three weeks later Basulto’s plane and two other BTTR Cessnas took off from Opa-Locka airport in Miami and attempted to penetrate Cuban airspace once again The Cuban air force scrambled its MiG fighters and shot two of them down killing four pilots and copilots and generating a major international crisis Castro was livid at what he considered Clinton’s betrayal Clinton announced new sanctions against the Castro regime and promptly signed a draconian piece of legislation—sponsored by Senator Jesse Helms and Congressman Dan Burton—known as the Cuban Liberty and Democratic Solidarity Act codifying the trade embargo into law and severely restricting the power of future presidents to fully normalize relations with Cuba without Congressional approval A CIGAR FOR OBAMA In the 18 years since the shoot-down and passage of the Helms-Burton bill U S –Cuban relations have remained largely caught in a Cold War time-warp despite  changes in both nations In Cuba Fidel Castro fell ill in July 2006 and passed the baton of power to his brother Raúl who is currently leading the country through a slow and difficult transition from a Soviet-style centrally planned economy to a socialist market economy  modeled on Vietnam and China In the United States opinion polls now show a majority of U S citizens and more importantly Cuban-Americans in Florida favor normal relations Yet the embargo persists as do U S efforts to foster regime change in Cuba through semi-covert “democracy promotion programs ” The United States is now the only nation in the Western Hemisphere that does not have fully normal diplomatic and economic ties with Cuba To be sure President Obama understands the folly of this 124 self-defeating posture “We’ve been engaged in a failed policy with Cuba for the last 50 years and we need to change it ” he declared as a candidate in 2007 To his credit he has expanded “people-to-people” travel to Cuba and lifted all restrictions on the ability of Cuban-Americans to visit their families on the island While the tone of relations has changed for the better however the overall policy has not In his first six years in office Obama has failed to lift the ban imposed by his predecessor on bringing home even one box of Cuban cigars from Havana let alone moved U S policy toward Cuba into the 21st century With two years to go in Obama’s presidency conditions for a rapprochement between Washington and Havana seem more propitious than ever Facing no more elections Obama no longer has to concern himself with the political implications of using his presidential powers to advance relations Nor does he need to worry about the impact on his would-be successor Hillary Clinton who has already stated publicly that the embargo is counterproductive to U S interests   Obama’s legacy would be aptly served by breaking the enduring logjam of Cuba policy Hemispheric diplomacy will soon provide him with an opportunity—should he choose to take it Like Kissinger in 1974 Obama confronts a rebellion of Latin American nations demanding that Cuba no longer be excluded from regional affairs  Despite Washington’s objections Panama which is hosting the Seventh Summit of  the Americas next April has invited Cuba Raúl Castro’s government has indicated that he will participate Obama will likely attend rather than boycott and “The United STates seeks a New beginning with Cuba I know there’s a longer journey that must be traveled to overcome decades of Mistrust ” —President Barack Obama in 2009 risk damaging U S relations with the entire hemisphere if so the presidents of the United States and Cuba may well come face to face in a working diplomatic forum for the first time since the 1959 Cuban revolution “The United States seeks a new beginning with Cuba ” Obama declared at the first Summit of the Americas he attended in 2009 “I know there’s a longer journey that must be traveled to overcome decades of mistrust but there are critical steps we can take toward a new day ” One such step would be for Obama and Castro to seize the opportunity at the forthcoming summit to sit down and talk informally about how to improve U S -Cuban relations which both have stated they want to do   Perhaps Raúl will bring Obama a box of Cohiba Lanceros as a peace offering Then they can smoke a Cuban  together while they contemplate how to move beyond more than 50 years of hostility that no longer serves the interests of either nation toward  a new beginning and a new day in U S -Cuban relations v Peter Kornbluh and William M LeoGrande are coauthors of the just-published book Back Channel to Cuba The Hidden History of Negotiations Between the United States and Cuba Univ of North Carolina Press October 2014