Fidel Castro and James Donovan fishing at the Bay of Pigs, April 8, 1963. Castro is wearing a scuba-diving watch given to him by Donovan.(John B. Donovan)

In early April of 1963, a New York lawyer named James Donovan traveled to Havana to negotiate the release of US citizens being held in Cuban jails. He carried with him page proofs of an article titled “How Metadiplomacy Works: James Donovan and Castro,” soon to be published in the
April 13 issue of The Nation. In a conversation with Fidel Castro that lasted from 2:15 to 6:30 am, Donovan read the article out loud and discussed it at length with the Cuban comandante and his top aide. “I explained the great tradition of The Nation,” Donovan later recounted, and Castro was “enormously interested.” According to Donovan, Castro “thought that this article was excellent, that it showed wisdom. That was his word—
wisdom.” The Cuban premier promptly ordered that it be translated into Russian and shared with the Soviet ambassador, who pronounced himself “very pleased with the entire tenor of the article” and said that he hoped it would be a “constructive step forward to a solution of the problems over Cuba.”

Written by the renowned New York Times Magazine staff writer Gertrude Samuels, the Nation article examined the first real dialogue between Washington and Havana after the rupture of official relations in January 1961. Donovan “has been the sole direct channel between the United States and Cuba,” Samuels reported. “Ostensibly a private citizen” and a “volunteer” with no diplomatic status (it was not publicly known at the time that Donovan’s missions were overseen by Attorney General Robert Kennedy and the CIA), he had negotiated the release and return to the United States of 1,163 members of the CIA-led exile brigade captured by Cuban forces at the Bay of Pigs in 1961. In addition, he had secured the departure of some 3,500 of their relatives after the 1962 missile crisis. The article also detailed Donovan’s ongoing effort to obtain the release of thirty-one US citizens whom Castro had imprisoned as spies and saboteurs. By winning not only the release of more than a thousand prisoners but also Castro’s confidence, Samuels pointed out, Donovan had become by 1963 the “most successful American practitioner of metadiplomacy—higher diplomacy”—with Cuba.

Fifty years after the article was written, “metadiplomacy” continues to hold lessons for Washington’s approach to Cuba. Donovan “holds the stubborn hope that his current mission will broaden beyond the immediate rescues—that he is setting the stage for some sort of conciliation between the American and the Cuban people,” Samuels reported. “I do believe that in these negotiations there does lie the greatest hope of creating some equitable solution to the problems now affecting relations between the two countries,” he told her. His unique diplomatic effort remains relevant to the search for an “equitable solution” to the problems that continue to plague US-Cuban relations.

James Donovan became known as “the negotiator” for secretly arranging the famous Cold War prisoner swap of Soviet spy Col. Rudolf Abel for the American U-2 spy plane pilot Francis Gary Powers, who had been shot down over the Soviet Union in 1960. After several weeks of clandestine diplomacy, the exchange took place in February 1962 on the Glienicke Bridge in Berlin. Six months later, President Kennedy turned to Donovan to obtain the freedom of the Bay of Pigs prisoners. Officially representing the Cuban Families Committee for the Liberation of the Prisoners of War, Donovan traveled back and forth between New York and Havana throughout the early and late fall of 1962 (the negotiations were interrupted by the dramatic discovery of Soviet missiles on the island), securing their freedom on Christmas Eve in return for $62 million in US shipments of food, pharmaceuticals and medical equipment. As those intense negotiations culminated in late December, the CIA asked Donovan to obtain a Christmas “bonus” from Castro: the additional release of twenty-two American citizens incarcerated in Cuba as spies. (Three of them were members of a CIA team of audio technicians caught in September 1960 planting listening devices in the Havana offices of the New China News Agency.) “I’ve already done the loaves and fishes,” Donovan told his colleagues. “Now they want me to walk on water, too.”

Drawing on the good will and close confidence that he had established with Castro, Donovan returned to Havana on January 26. He carried a proposal for a prisoner swap: the US citizens for four Cubans in US jails. They included one Cuban attaché at the UN mission and two Cuban residents of New York who were under indictment for planning acts of sabotage there; the fourth was a Cuban convicted of second-degree murder for killing a 9-year-old girl. (She was struck by a stray bullet during a brawl with anti-Castro Cubans when Castro spoke at the UN in September 1960.) Castro appeared interested. As Donovan was boarding his plane for the States, however, Castro’s aide-de-camp, Dr. René Vallejo, took him aside and expressed an additional Cuban interest: the re-establishment of diplomatic relations with Washington.

When Donovan returned to Havana on March 14, nine additional US citizens were part of the deal—hapless skin divers whose life raft had washed up on a Cuban beach after their boat sank. If Donovan could convince him that they were not saboteurs, Castro said, he would let them go. In their negotiations, they agreed to avoid defining the exchange as a prisoner swap. Castro would grant clemency to the American prisoners in recognition of the final April shipments of medicine from the Bay of Pigs deal; the United States would subsequently release the Cuban prisoners, also as an act of clemency. As a gesture of good will, Castro allowed Donovan to take with him upon his departure two American women: Geraldine Shamma, a socialite recruited by the CIA to spy on Castro, and Martha O’Neal, both of whom had been jailed in 1960 for counterrevolutionary activities.

Donovan flew to Havana on April 5 to finalize the exchange, bringing three diplomatic stage-setters: the page proofs of the Nation article, a Polaroid camera as a gift for Castro, and his teenage son John. His son was “the ultimate in gamesmanship,” Donovan later noted, according to Phillip Bigger’s biography of him, Negotiator. “Castro has a fourteen-year-old boy. I hoped that the presence of my eighteen year old would inspire confidence and make a favorable impression on Castro.” Indeed it did. Castro took Donovan and his son on a daylong fishing expedition to the Bay of Pigs—Fidel personally speared fifteen fish, one of them a forty-pounder—gave them a tour of a new crocodile farm and workers’ vacation resort nearby, and took them to a kids’ baseball game. Fidel was “very pleased” that “I would bring over my only son,” as Dr. Vallejo informed Donovan. Castro “wanted to make certain that my only son was shown everything and treated well,” and Cuba’s leader felt “greatly complimented that I would have this much confidence in him to do this.”

In their negotiations, Donovan deftly used the Nation article to dangle the prospect of better relations with Washington if the prisoner release succeeded. The profile in The Nation, along with major coverage in Look, Life and The Saturday Evening Post, he suggested, reflected a shift in American attitudes toward the Cuban Revolution in the aftermath of the missile crisis. The average citizen, Donovan told Castro, “simply could not see involving the U.S. in nuclear warfare to vaguely restore Cuba to Batistaville”—a reference to the era of Fulgencio Batista, the US-backed dictator overthrown by the Cuban Revolution. The American public didn’t want Cuba to become a Soviet satellite, he said, but “so too I didn’t think that the people in the U.S. were intent on his being a satellite of the U.S.; that the integrity of the revolution would be respected as long as his every effort was dedicated to the betterment of the Cuban people.”

When Castro asked what the impact of the Nation article would be, Donovan told him, “I thought it would be immediately studied by intellectuals, liberals, editorial writers, and various molders of public opinion; that it would also be studied in government circles.” According to a transcript of a CIA debriefing with Donovan after he returned, he paid the ultimate compliment to the magazine: “I said that I thought that whereas the articles in Life and Look were reflecting general public opinion, the article in The Nation was one attempting to lead public opinion.”

Their discussion of the article led directly to the very first serious conversation between Castro and a US representative about how to normalize relations between Washington and Havana. As Donovan later related in the CIA debriefing, “He said well, in view of the past history on both sides here, the problem of how to inaugurate any relations was a very difficult one.” To which Donovan replied, “Are you familiar with porcupines?” Castro said he was. “So I said, now do you know how porcupines make love? And he said no. And I said well, the answer is ‘very carefully,’ and that’s how you and the U.S. would have to get into this, but on the specifics this would have to be left to common sense diplomatic discussions.”

When Donovan flew back to Florida on April 9, he was accompanied by the nine skin divers and one missionary that Castro determined could be freed. The Cuban leader seemed persuaded by Donovan’s arguments that the prisoners were a stumbling block to better relations with the United States. “Now you’ve shown me the article in The Nation,” Castro told Donovan, “I’m prepared to take a chance on your analysis of the situation and your prophecies on what should happen.” Holding the Americans as “a bargaining asset” was not in Cuba’s interest, he conceded, because “perhaps it’s preventing something more constructive from being accomplished.” Castro promised that if Donovan returned on April 22, “I’ll release all of them to you.”

Two weeks later, Donovan returned to Havana one last time. As promised, Castro released twenty-seven more US citizens; twenty-one of them, including the three CIA agents, returned with the US negotiator to an Air Force base near Miami. The same day, Kennedy’s Justice Department released the four Cubans in New York “in the national interest.” They were flown to Florida and then repatriated to Havana.

Castro clearly hoped that US-Cuban cooperation on the prisoners would clear the way for better ties. “He thought the Kennedys were sort of fumbling toward a policy here and that perhaps the holding of these prisoners was preventing the formulation of a clear policy,” Donovan reported to his CIA handlers. Once the prisoner problem had been resolved, he added, the Cuban government believed the Kennedy administration would develop an approach that would be “constructive and in [its] best interests.”

In the spring of 1963, the Kennedy White House did begin to reconsider the merits of a more constructive approach to Cuba. Although Donovan was not involved as a negotiator, as both he and Castro had hoped, in the fall the administration used other intermediaries to pursue a secret dialogue with Cuba. In a cruel coincidence of history, on the very day Kennedy was assassinated, one of his emissaries was meeting with Castro in Varadero Beach near Havana “on a mission of peace” for future US-Cuban relations.

Fifty years later, the legacy of Donovan’s “common sense” diplomacy continues to resonate. Indeed, in 2013 Washington and Havana are still in need of a “metadiplomat” to resolve their differences. The circumstances are similar: Cuba, under the leadership of Raúl Castro, has repeatedly expressed an interest in dialogue; American public support for normalized relations has increased considerably; and, like Kennedy, President Obama appears to be “sort of fumbling” for a better policy. But once again, prisoners in both countries are proving to be a stumbling block to negotiations. The Cubans are holding US subcontractor Alan Gross, now in his fourth year of incarceration for illicitly attempting to set up a satellite communications network in Cuba as part of the US Agency for International Development’s Cuba Democracy and Contingency Planning Program. And the United States is holding the “Cuban Five,” who include four Cuban spies, now in their fifteenth year in prison for conducting espionage operations, mostly against exile groups with violent pasts, and one agent who has been paroled but remains legally confined to Florida. Just as Fidel Castro stressed the concept of clemency in the prisoner swap of 1963, Raúl Castro has called for mutual “humanitarian gestures” to resolve these obstacles to improved bilateral relations.

Donovan’s history lesson in “how metadiplomacy works” demonstrates that, with creativity and perseverance, a deal between the United States and Cuba is doable. A dialogue that includes the prisoner issue remains “in the national interest” of both countries, and it could lead to broader and better ties. Fifty years later, it is possible to fulfill Donovan’s “stubborn hope” for normal relations. As he told The Nation in 1963, “This is work requiring great patience.”