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Talking with Castro

For most of the last 50 years, nearly every U.S. president has negotiated secretly with the government of Cuba in bids to resolve the two nations' conflicts
Peter Kornbluh, William M. Leogrande
From the Print Edition:
Cuba, January/February 2009

In late August of 1994, the Nobel Prize—winning novelist Gabriel García Márquez traveled to Martha's Vineyard for a dinner with President Bill Clinton. "Gabo wanted to come and talk to Clinton about Cuba," recalled Rose Styron who, along with her famous husband, William, hosted the evening at their rambling island home. Indeed, the dinner party served as an elaborate cover for García Márquez to deliver a message to Clinton from Fidel Castro. While the other guests ate fried chicken with rice and gravy, the writer shared with the president details of Castro's proposal to end the "balsero crisis"—the flood of Cubans taking to the seas in small boats, inner tubes and makeshift rafts to cross the Florida Straits to the United States. As Rose Styron remembers, García Márquez also took the opportunity to press Clinton on "the need to open up relations" with Cuba; Clinton, she said, appeared to agree. "Try and come to an understanding with Fidel, as he has a very good opinion of you," García Márquez advised the president. The next day, García Márquez left the Vineyard and traveled to Havana to report on Clinton's response to Castro.

This furtive communication between a U.S. president and the fiery Cuban leader was no historical anomaly. Clinton was hardly the first U.S. president to negotiate with Castro, discreetly, through an intermediary. It is a little-known fact that since the Eisenhower administration broke relations with Cuba on January 3, 1961, every president has engaged in some form of dialogue with Fidel Castro—with the exception of George W. Bush. From Kennedy to Clinton, one U.S. administration after another has negotiated immigration accords, anti-terrorism treaties, counter-narcotics agreements and other bilateral arrangements. Behind the scenes, the United States and Cuba have repeatedly resorted to clandestine diplomacy to address and resolve crises, ranging from tensions at the U.S. military base at Guantánamo to terrorist plots against Cuba. Several presidents—most notably Kennedy, Ford and Carter—engaged in secret dialogues with Castro to explore the normalization of relations.

This history has immediate relevance for the new president of the United States. During his campaign, Barack Obama raised expectations about a change in Cuba policy when he pledged to meet with leaders of hostile states such as Iran and North Korea "without preconditions." Asked during a debate with Hillary Clinton in Texas if he would actually sit down with Raúl Castro in Cuba, Obama replied:

That's correct.... I would meet without preconditions, although Senator Clinton is right that there has to be preparation.... And that preparation might take some time. But I do think that it's important for the United States not just to talk to its friends, but also to talk to its enemies. In fact, that's where diplomacy makes the biggest difference. Preparations for such diplomacy should include a review of past efforts by Obama's predecessors to talk with Fidel about changing the hostile framework of relations that has endured for 50 years. Kennedy, Ford and Carter failed to reach an accommodation with Cuba. Clinton's efforts to reduce tensions and improve relations also fell short of that goal. But the historical record generated by their administrations contains important lessons on how an effective effort at direct diplomacy might end, once and for all, the perpetual antagonism in U.S.-Cuban relations.


In his youthful demeanor and charisma, Obama has often been compared to John F. Kennedy. The Cuban issue dominated Kennedy's thousand days in office. As president, he led the country and the world through the Cuban Missile Crisis; he also oversaw some of the most egregious acts of U.S. aggression toward the island nation, including the failed Bay of Pigs invasion, the trade embargo and Operation Mongoose, a set of covert actions designed to destabilize the country and overthrow Castro. But Kennedy also had the courage and curiosity to explore what Top Secret National Security Council memoranda described as "U.S./Cuban discussions about accommodation" and "a rapprochement with Castro."

Early in his administration, Kennedy learned that the Cubans were open to such talks. During an international economic summit in Montevideo, Uruguay, in August 1961, Che Guevara arranged an all-night meeting with White House aide Richard Goodwin—by using an Argentine diplomat as an intermediary to dare Goodwin to smoke a Cuban cigar. Che emphasized several salient points that would be repeated in almost all future negotiations and remain relevant today.

First, as Goodwin wrote in a secret memorandum of conversation to President Kennedy, Cuba was clearly interested in a dialogue that would lead to coexistence. "They would like a modus vivendi—at least an interim modus vivendi," Goodwin reported. Second, although Castro was willing to make a number of concessions toward that goal, the nature of Cuba's political system was nonnegotiable. "He said they could discuss no formula that would mean giving up the type of society to which they were dedicated." Finally, Guevara raised the issue of how the two countries would find "a practical formula" to advance toward an accommodation. He made a pragmatic suggestion—one that Cuba would invoke again and again in pressing for a diplomatic dialogue over the next 48 years: "He knew it was difficult to negotiate these things but we could open up some of these issues by beginning to discuss secondary issues … as a cover for more serious conversation."

To demonstrate just how serious the Cubans were, Che gave Goodwin an engraved mahogany box of premium Cuban cigars for Kennedy—a gift representing Cuba's first attempt, although not its last, at "cigar diplomacy" aimed at a U.S. president.

When Goodwin returned to Washington, he recommended seeking "some way of continuing the below ground dialogue which Che has begun." He even tasked the CIA to develop a "precise, covert procedure for continuing below ground dialogue with the Cuban government" to maintain secrecy around such politically sensitive talks. But the rest of the administration ignored Cuba's overture. "The emotion that had always surrounded the 'problem' of Cuba had, if anything, been heightened by our defeat at the Bay of Pigs," Goodwin later wrote. "To make a deal with Castro, any kind of deal, would have been politically difficult, perhaps impossible."

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