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Cigar Diplomacy

As the United States and Cuba have attempted to negotiate their differences over the last 50 years, Cuban cigars have played a diplomatic role in secret efforts to improve relations
| By Peter Kornbluh , William M. Leogrande | From Michael Strahan, November/December 2014
Cigar Diplomacy

In September of 1980, President Jimmy Carter dispatched a special envoy to Havana to meet secretly with Fidel Catro and negotiate a resolution to a major immigration crisis—the mass exodus of tens of thousands of Cubans from the port of Mariel. During their meeting, Castro agreed to close the port, stanching the flow of refugees across the Florida Strait. The presidential envoy, a seasoned diplomat named Peter Tarnoff, promised that the Carter administration would pursue a broader dialogue on better relations with Cuba in a second term if the president won his bid for re-election.

When Tarnoff returned, he briefed the president and Secretary of State Edmund Muskie in the Oval Office on the positive results of his discussions with the Cuban comandante. He also delivered a gift from Castro to Muskie: a big box of Cuban cigars. As the meeting adjourned, Muskie eagerly unwrapped the elaborate packaging. “But he was disappointed,” Tarnoff recalled, “when under all the wrapping, it held just 100 cigars—the legal limit for what could be brought into the United States.”

Even though the trade embargo has banned or limited their availability in the United States, Cuban cigars hold a special place in the controversial history of U.S. relations with Castro’s  revolution. The first president to order the economic sanctions, John F. Kennedy, famously sent his press secretary Pierre Salinger on a cigar buying spree before signing the Cuba embargo decree—some 1,200 Cuban cigars were purchased for JFK’s private stash of smokes. At the height of the Cold War, the CIA concocted a plot to assassinate Castro by sabotaging his cigars. According to a Top Secret report on the many failed CIA efforts to kill Castro, the agency’s Office of Medical Services contaminated a box of 50 of “Fidel’s favorite brand” with a botulinum toxin—“a virulent poison that produces a fatal illness some hours after it is ingested.” The cigars were so heavily poisoned that “the intended victim would not actually have to smoke it,” the CIA report noted. “[M]erely putting one in the mouth would do the job.”

But Cuban Cohibas, Montecristos and Romeo y Juliets have also played a positive role in bridging the ideological chasm between Washington and Havana.  During secret attempts at reconciliation, an untold story compiled in a new book, Back Channel to Cuba: The Hidden History of Negotiations Between Washington and Havana, Fidel Castro’s government made active and 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.


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 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 to 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, while 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 admin-istration “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. But 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….”


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 by one, Latin American nations were breaking with the multilateral embargo that the OAS, under U.S. pressure, had passed in 1964 banning economic and diplomatic ties with Cuba. In the summer of 1974, the OAS had scheduled a vote to lift the multilateral sanctions (which would finally be lifted in 1975). “We have a poor hand to play and should ask for a new deal before we lose our last chip,” one aide warned Kissinger in a classified memorandum on the need to negotiate with Castro before the OAS vote.

The Secretary of State agreed. Kissinger decided to make a virtue out of necessity and use these diplomatic circumstances as an opportunity for an historic accord with Cuba. In late June of 1974, he sent a secret, handwritten, note to the Cuban leader. Kissinger’s message—unsigned in order to maintain plausible denial if it leaked—stated that he was anxious to discuss bilateral issues and hoped “to find a way to communicate.”

Such discussions needed to be conducted discretely, using intermediaries. “This is the way I did it with Chou En-lai,” Kissinger informed 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 Washington, Castro gave Mankiewicz, Jones and Landau a special box of Cohibas. “This is a box for Henry Kissinger,” he told them. Since travel between Havana and Miami was prohibited at the time, Castro provided his private plane to fly them to Nassau, so that they could more quickly return to the States and give Kissinger both his note and the cigars.But in Nassau, Castro’s effort at cigar diplomacy was almost thwarted by a disciplined customs officer.  “We had 12 boxes of cigars,” Kirby Jones 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, “Oh my God, what do we have here?” As the agent threatened to confiscate all of the cigars as contraband, Mankiewicz stood up for cigar diplomacy.  “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 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 them as he relented, “you deserve to take them.” Mankiewicz completed his mission, delivering the cigars to the Secretary of State.

So began the most serious diplomatic effort to normalize relations since Washington broke ties with Havana in January 1961. Over the next 18 months, Kissinger and Castro’s emissaries traveled back and forth between Washington and Havana; holding furtive meetings in lounges at La Guardia and National airport, the private homes of U.S. officials and even the swanky Pierre Hotel in New York City to address the issues that had divided the two countries since the 1959 revolution. “It is better to 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 CIA-supported 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.”


The Carter administration attempted to pick up on the Kissinger initiative and made significant early gains in establishing at least partial diplomatic relations through the creation of “Interest Sections” in Havana and Washington that functioned like Embassies. But the administration demanded that Castro get his troops out of Africa before the embargo could be lifted and relations fully normalized. Castro’s attempt in the fall of 1980 to help Jimmy Carter’s chances for reelection by ending the Mariel boatlift—and to curry favor with Secretary of State Muskie with a diplomatic gesture of 100 premium cigars—proved to be too little and too late. There would be no second term for  Carter—he lost to Ronald Reagan in a landslide—no second chance to pursue normalizing relations with Cuba. “I think in retrospect, knowing what I know since I left the White House,” the former president later admitted in an interview with the authors, “I should have gone ahead and been more flexible in dealing with Cuba and established full diplomatic relations.”

Neither Ronald Reagan nor the administration of George H.W. Bush offered much opportunity for cigar diplomacy with Cuba. But Bill Clinton was known to love a good Cuban cigar. The Clinton administration engaged in a series of open and back-channel talks with the Cuban 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,” he boasted. “The regime is not invulnerable.”

For a country with a long history of exile terrorism, including bombs dropped from small airplanes on the countryside, these overflights were not only a violation of Cuban sovereignty; the Cubans perceived them as a serious threat to national security. The Castro government used every available channel of communication—formal diplomatic notes, official letters to the FAA, direct phone calls to the State Department and a 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 BTTR flights. He also called Richard Nuccio, the Special Advisor to the president and secretary of state for Cuban Affairs, and asked him to come to Richardson’s Capitol Hill office.  “He reached under his desk and pulled out a duffle bag full of cigars.” Giving Nuccio a box, he said, “Get this to the president,” Nuccio recounted in an interview with the authors.

Nuccio took the box directly to the West Wing office of national security advisor Samuel Berger. “I have a box of cigars. A personal gift from President Castro to President Clinton,” Nuccio told him. “Would you like to give it to him?”

In an election year in which Florida would be a swing state, Berger understood the potential political implications of Clinton receiving banned Cuban cigars from Fidel Castro. “Those cigars will never get to the president,” he sternly instructed Nuccio. “The president will never know you have those cigars. They are leaving this office right now and 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.


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 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 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.

Peter Kornbluh and William M. LeoGrande are coauthors of the just-published book, Back Channel to Cuba: The Hidden History of Negotiations Between Washington and Havana (University of North Carolina Press, October 2014).

"Cold-war time-warp? Castro's just a misunderstood nice guy, right?" —January 4, 2015 09:53 AM
"Awesome read. Thank you for posting this and I hope it gets shared around." —December 31, 2014 18:14 PM

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