The Negotiator

The inside story of James Donovan, who sat face-to-face with Fidel Castro, negotiated the release of hundreds of prisoners and opened the door to diplomacy between the U.S. and Cuba
| By Peter Kornbluh | From Steve Harvey, March/April 2017
The Negotiator
Photo: Marty Lederhandler/AP Photo

Fidel Castro and a New York insurance lawyer named James Donovan stood together on the tarmac of San Antonio de los Baños Airfield in Cuba and watched as hundreds of just-released prisoners of war boarded a caravan of planes bound for Miami. It was December 23, 1962. Only the night before, Castro had given Donovan an ornate humidor filled to the brim with 200 cigars—a gift to celebrate the successful culmination of a long, contentious set of negotiations to gain the freedom of the CIA-led exile invasion force defeated and captured at the Bay of Pigs in April 1961.

Donovan was the most famous international negotiator in the United States, if not the world. In early 1962, he had
arranged a prisoner exchange with the Kremlin—the release of Francis Gary Powers, a CIA U-2 pilot shot down over Russia while on a reconnaissance mission, for veteran KGB spy Col. Rudolf Abel, captured by the FBI in New York. With all the drama of a Hollywood thriller, the Cold War spy swap took place in the middle of the Glienicke Bridge connecting West Berlin to Potsdam. Donovan's secret negotiations with the Russians were immortalized in Steven Spielberg's Oscar-nominated movie, Bridge of Spies, starring Tom Hanks as Donovan.

Donovan's dramatic negotiations with Castro are equally worthy of a major Hollywood film. They marked the first serious dialogue between Washington and Havana, and led to the first serious discussions of improving U.S.-Cuban relations. In many respects, James Donovan's face-to-face talks with Fidel Castro set the historical stage for former president Barack Obama's rapprochement with Cuba more than 50 years later. As the United States and Cuba enter the post-Obama/post-Fidel Castro era, the story of Donovan's historic negotiations with the Cuban commandante provides a historical parable for successful diplomacy—one that carries important implications for the future of relations between Washington and Havana.

A Donovan family photo of the negotiator with Fidel Castro.
Courtesy of the Donovan family
A Donovan family photo of the negotiator with Fidel Castro.

Project Mercy

The CIA-sponsored paramilitary invasion at the Bay of Pigs remains the most flagrant symbol of U.S. intervention in the long and dark history of conflict between Washington and Havana. From that disastrous act of aggression, however, evolved the first significant opportunity for serious negotiations between the two countries—and the first sincere effort to improve relations.

John F. Kennedy inherited the CIA's plan to invade Cuba from the Eisenhower administration. To maintain a veneer of deniability of a U.S. role, the president pushed the CIA to change the landing site from the populated city of Trinidad to a remote location where the invaders could establish a beachhead before being discovered by Castro's forces. But Cuban militiamen on guard at the Bay of Pigs in the middle of the night spotted the beacon lit by a CIA operative to guide the exile brigade from the dark waters to the beach on April 17, 1961; the element of surprise was lost. Within 72 hours, Castro's forces defeated the CIA's exile brigade. "They trusted me. And they are in prison now because I fucked up," Kennedy told his White House aide, Richard Goodwin. "I have to get them out."

Castro promptly offered Kennedy a way to barter the release of the brigade: 500 Caterpillar tractors and spare parts as "indemnification" for the death and destruction caused by the invasion. To avoid direct negotiations, the president secretly established the "Tractors for Freedom Committee," recruiting four American luminaries (including former First Lady Eleanor Roosevelt) to lead it. But their negotiating strategy with Fidel—a take-it-or-leave-it approach of dictating terms and deadlines—failed, and the Committee disbanded only six weeks after it was created. Over the next year, Castro put the captured soldiers on trial, and announced that fines for their crimes amounted to $62 million—the price of their freedom. In June 1962, Attorney General Robert Kennedy secretly recruited Donovan to re-open talks with the Cuban leader.

Publicly, Donovan represented the Families Committee of the Bay of Pigs Prisoners. Privately, he would be negotiating on behalf of the White House, with active CIA support. "Every attempt to extricate ourselves from this whole Bay of Pigs episode has failed," the attorney general told Donovan at their first meeting on July 3, 1962. CIA director John McCone instructed Donovan to "immediately proceed to attempt to open negotiations with the Castro government, with the twin objectives of 1) lowering the minimum amount demanded by Castro and 2) arranging that a substantial part of this sum would be payable in food and medicine." 

McCone authorized the creation of a secret CIA task force, codenamed "Moses," to support Donovan's efforts. Agency officials set up a safe house in Miami for Donovan with a secure phone to use on his way to and from Havana. They gave him special communication devices and a code sheet to use when calling his CIA handlers from Cuba. Fidel would be referred to as "Erie," according to CIA codes; Che Guevara's designation was "Fulton." The code word "Hamilton" meant that negotiations were "difficult, progressing" but had "some hope for a settlement." The CIA's code-name for Donovan's special rescue mission was "Project Mercy."

Donovan quickly received an invitation to travel to Havana. On August 31, 1962, he sat down with Castro for the first time. "Met at Presidential palace with C," reads Donovan's personal chronology of the talks. "Offer[ed] drugs and baby food for men. But no cash or tractors. 4 hrs."

Donovan with U.S. Attorney General Robert F. Kennedy.
Courtesy of the Donovan family
Donovan with U.S. Attorney General Robert F. Kennedy.

During this first negotiating session, Castro treated Donovan to two lengthy diatribes about the historical atrocities committed against Cuba by the United States. But Donovan maintained a gracious and solicitous tone. He referred to Fidel as "Dr. Castro"—Castro returned the favor by calling him "Dr. Donovan"—and generally accepted his demand for U.S. "indemnification" for the human and material damages caused by the invasion. How much and in what form that "indemnity" would take was the focus of their negotiations. Donovan explained congressional restrictions on cash payments to Cuba, and stressed, according to his notes, that it would be better for Cuba's image not to "sell humans." Castro could gain the sympathy of U.S. citizens by releasing the prisoners. "Two peoples can work together to solve a problem, you know," he told Fidel.

By the end of this first session, Castro and Donovan had arrived at a general framework of an accord. Cuba would accept a cash payment of $2.9 million for 60 prisoners who Fidel had already allowed to return to the U.S. for health reasons. The rest of the indemnity would be paid with foodstuffs, medicines and related pharmaceutical supplies whose retail value, rather than wholesale value, approximated $60 million. Castro commended Donovan on his attitude and approach, in contrast to the Tractors for Freedom Committee. "Things would have been very different then," Castro said, "if we would have been treated in another manner."

Donovan returned to Cuba on October 3 to meet Castro at the Dupont mansion on Varadero Beach. This second round of negotiations did not go as smoothly. Castro challenged the calculations for the retail values of the goods; more importantly, the Cuban leader refused to agree to Donovan's request that all prisoners be released after the first shipment. Over Donovan's objections, Fidel wanted to release them in stages as each shipment arrived. In a message to Castro drafted before he returned to Florida, Donovan dangled better relations as the ultimate reward for quickly releasing the prisoners: "the happy termination of this negotiation in good faith could create a bridge between the United States and Cuba," he wrote, "favorable for each in the current international situation."

These issues remained unresolved when Donovan returned to Havana a week later. By then, details of the proposed accord had leaked to the New York Herald Tribune, bringing unwanted publicity to the effort to finalize the deal. When Fidel re-opened discussions on the pricing and types of materials and medicines Cuba wanted, Donovan forcefully
reminded him that his proposal was Cuba's only option to dispose of the Bay of Pigs prisoners. "You can't shoot them," Donovan noted. "If you want to get rid of them, if you want to sell them, you have got to sell them to me," Donovan declared. "There's only one market for your prisoners of war and I'm it!" On October 11, he returned to Miami empty-handed, still hoping that the talks would be finalized within a few days.

Only four days later, a CIA analyst reviewing reconnaissance photos of the Cuban countryside identified Soviet intermediate range missile sites under construction. As the dangerous superpower showdown known as the Cuban Missile Crisis unfolded, CIA director John McCone convinced President Kennedy to suspend the Donovan-Castro talks. "If definitive news of the secret talks came out," McCone argued, "public reaction could be severe and make resolving the missile crisis harder." Even after the missile crisis ended, McCone lobbied the White House against giving Donovan the green light to restart the prisoner negotiations. If the secret White House-CIA role leaked, he told Robert Kennedy, the American public "and many others" would be "confused and disenchanted" to learn that the U.S. was conducting back-channel talks with the Cuban revolutionary who had just placed the fate of the entire world in jeopardy.

On November 20, however, Donovan informed the attorney general that Castro was ready to make a deal. Castro's interest, and increased public pressure from the relatives of the prisoners, prompted Robert Kennedy to assign one of his top aides at the Justice Department, John Nolan, to assist Donovan in bringing the brigade members home by Christmas. Within only a few weeks, they finalized an arrangement with a number of major pharmaceutical companies, among them Pfizer and Ely Lilly, and food companies to contribute shiploads of supplies from their older inventories in return for tax breaks. President Kennedy was so anxious to see the negotiations completed that he floated the idea of his brother taking a secret trip to Havana to finalize the accord. "The President wants the Attorney General to go down [to Cuba] because he now has commitments to cover the Castro list," CIA Director McCone reported to State Department officials on December 14, 1962.

Fidel gave Donovan and Nolan the red-carpet treatment when they returned on December 18. As the final negotiations began, according to a detailed book, After the Bay of Pigs, Donovan set the stage with some humor. "The main problem now is that I have decided to ask Santa Claus to join our working team in the United States," Donovan told Castro. "But we must recall that he goes out of business after December 25th. We should therefore take advantage of the holiday spirit in the United States and attempt to conclude negotiations now. Time is of the essence because of political opposition within the United States and within the Cuban community in the States."

Substantive obstacles remained. Castro was so distrustful about the quality and contents of the initial shipment that Donovan arranged for a clandestine nighttime trip to Miami for three of his aides to inspect the medicines being loaded onto the cargo ship, the S.S. African Pilot. Castro also refused to accept additional drugs in lieu of the $2.9 million promised him by the Families Committee for the earlier release of 60 prisoners who needed medical attention; he threatened to keep the leaders of the exile brigade in jail unless the money was delivered. Robert Kennedy was forced to raise the funds from private donors at the last minute to secure their freedom.

On December 21, Donovan and Castro representatives finally signed a "Memorandum of agreement between the Government of Cuba and the Cuban Families Committee for the Liberation of the Prisoners of War." The accord allowed 1,113 Bay of Pigs prisoners, and eventually thousands more of their relatives, to leave in return for multiple shipments of goods valued at $53 million that began arriving on December 23. To celebrate, Castro presented Donovan with the cigars and Donovan shared a prayer of St. Francis. "Lord, make me an instrument of your peace," the prayer read in part. "Grant that I may not so much seek to be consoled as to console, to be understood as to understand."

As they watched the former prisoners depart two days before Christmas, Donovan spoke to Castro. "I want you to know that I appreciate your cooperation in many things throughout our negotiations," he said. "You have been very correct in your dealings with me." Castro returned the compliment. Donovan, he said, had been a skilled negotiator from whom Castro had learned many things. Castro invited Donovan to bring his family back to Cuba for a vacation at a state-provided villa on Varadero Beach, so they could "discuss the entire future of Cuba and Latin America and their relations with the United States."

CIA Dirty Tricks

Among the materials the United States began shipping to Cuba to complete the accord were hygienic supplies. A U.S. official, Col. Edward Lansdale, who was in charge of the sinister set of covert actions known as Operation Mongoose, saw an opportunity for creative psychological warfare against Cuba. In a proposal to the office of the CIA director, Lansdale suggested that the CIA print Fidel's image on the inside sheets of the rolls of toilet paper included in the shipments. The "earthy appeal of this is in tune with the Cuban sense of humor," Lansdale advised in a secret memo, "and they'd really get to laughing at Fidel." But his proposal to mount a "black propaganda" operation against Castro by doctoring the toilet paper was denied.

The toilet paper caper would not be the last time officials in charge of the dirty war against Cuba tried, and failed, to appropriate Donovan's work for aggressive purposes. In early 1963, a group of CIA officials devised a plot to turn his unique access to Castro into an opportunity to assassinate the Cuban leader. Their plan, a CIA internal history later reported, called for Donovan to become "the unwitting purveyor" of a poisoned scuba diving suit as a gift for Castro.

This scheme, according to a top-secret CIA report on plots to assassinate Fidel Castro, "progressed to the point of actually buying a diving suit and readying it for delivery." That meant "dusting the inside of the suit with a fungus that would produce a disabling and chronic skin disease (Madura foot) and contaminating the breathing apparatus with tubercle bacilli"—the bacterium that causes tuberculosis—said Sidney Gottlieb, then the head of the CIA's famous Technical Services Division (TSD).

But the operation was shelved after Donovan's CIA handler, Milan Miskovsky, learned of the plot and made sure the contaminated suit never left TSD's laboratory. Donovan obtained his own scuba diving suit for Castro—purchased at Abercrombie & Fitch—as a confidence-building gesture for new negotiations with Castro. But he and Miskovsky took steps to secure the gift from any tampering by the so-called "executive action" team at the CIA. "I was in the business of negotiation," Donovan would later exclaim, "not assassination!"

December 20, 1962. Longshoremen in Florida unload food and medicine bound for Cuba, part of the $53 million worth of U.S. goods sent for the release of the prisoners of war.
Photo/AP Photo
December 20, 1962. Longshoremen in Florida unload food and medicine bound for Cuba, part of the $53 million worth of U.S. goods sent for the release of the prisoners of war.

First Talks To Normalize Relations

Incredibly, the assassination plotters sought to sabotage Donovan's negotiations as he worked to obtain the freedom of three of their CIA colleagues. The three operatives had been caught in September 1960 placing eavesdropping devices in a Havana building that housed the Chinese News Service. To obtain their release without acknowledging their covert operations, CIA director John McCone asked Donovan to request "a Christmas present" from Castro—the release of all U.S. citizens in his jails along with the hundreds of Bay of Pigs exiles who were boarding planes on December 23, 1962. "Jesus Christ," Donovan exclaimed at the time. "I did the loaves and fishes, and now they want me to walk on water, too."

Castro pledged that if the delivery of the food and medicines continued smoothly, he would review the cases of U.S. citizens "in the near future." When Donovan returned a month later Fidel readily agreed to his proposal for a prisoner swap: four Cubans who had been arrested in the United States on various charges—one of them had accidently shot a nine-year-old girl in New York City during a brawl over Castro's visit to the United Nations in September 1960—for all the Americans in Castro's jails. He invited Donovan to return in March to finalize the exchange as well as to "talk at length" about the future of Cuba and international relations. When Donovan returned to the United States he reported to the CIA and the State Department that Castro's aide de camp, René Vallejo, had "broached the subject of reestablishing diplomatic relations with the U.S."


In Donovan, Fidel Castro had found the first U.S. interlocutor who he trusted enough to open the discussion about a modus vivendi with the United States. Given the rapport Donovan had established with the fiery Cuban leader, the Kennedy administration realized that Donovan could use his diplomatic skills to negotiate better relations with Cuba. Since President Kennedy believed that Castro's desire for talks "looked interesting," in the spring of 1963, U.S. officials undertook the first internal debate over whether, and how, to use Donovan to lead the U.S. and Cuba to normalized relations.

"There seems to be some possibility that Castro might be weaned away from the Communists if his idealism, his nationalism and his vanity are catered to," CIA officials wrote in a secret set of proposed negotiating instructions. "This is where Donovan comes in." The CIA wanted Donovan to set preconditions on Castro, among them to throw the Communists out, "lock, stock, and barrel." If Castro did not agree to all U.S. demands, Donovan should "paint for Castro...the permanently black picture that will prevail—with only one ultimate result—if Cuba continues to make the United States her enemy." Over at the State Department, officials concurred. Donovan should "take a weeklong walk on the beach" with Castro, stated one secret memo, and tell him "only two things are nonnegotiable, 1) Cuba's ties with the Sino-Soviet Bloc and 2) Cuba's interference with the hemisphere."

President Kennedy, however, took a far more tactful position. "We don't want to present Castro with a condition that he obviously cannot fulfill. We should start thinking along more flexible lines," he instructed his national security adviser, McGeorge Bundy. In a top secret/eyes only memorandum of conversation dated March 4, 1963, Bundy reported that "the President, himself, is very interested in this one."

On Christmas Eve, 1962, Donovan and Castro watched as the former prisoners climbed into planes in Cuba that would take them to the United States and freedom.
Photo: Alan Oxley/Getty Images
On Christmas Eve, 1962, Donovan and Castro watched as the former prisoners climbed into planes in Cuba that would take them to the United States and freedom.

Donovan returned to Cuba on March 14. He "was given the red-carpet treatment and had several long, cordial talks with Castro," according to a secret report prepared for President Kennedy. When Castro raised the issue of future ties to Washington, Donovan told him "better relations would probably result if Castro would just tend to his own knitting." As a gesture of goodwill, Castro released two American women, imprisoned as counterrevolutionaries, to accompany Donovan back to Miami.

On April 5, Donovan flew back to Havana to seal the deal. He brought three diplomatic stage-setters: a new Polaroid camera as a gift for Castro; the page proofs of a forthcoming article in The Nation magazine that highlighted the potential for the prisoner exchange to open the door to more normal relations, titled "How MetaDiplomacy Works: James Donovan and Fidel Castro;" and Donovan's teenage son, John.

Bringing his son along was "the ultimate in gamesmanship," according to Phillip Bigger's biography, Negotiator. "I hoped that the presence of my 18-year-old would inspire confidence and make a favorable impression on Castro," Donovan remembered. Indeed, Castro took Donovan and his son on a day-long fishing expedition to the Bay of Pigs, gave them a tour of a new crocodile farm, and took them to a baseball game. "A powerful key in my father's negotiating style was his tendency to bring it from the bureaucratic level to the human level," John Donovan recalled years later. In a subsequent interview with The New York Times, his father noted that "it was largely because I had brought the boy along that I was able that weekend to persuade Castro to release 35 American prisoners."

The prospect for better U.S.-Cuban relations was the real reason Castro was persuaded to release the prisoners. The article in The Nation, along with major coverage in Look, Life and The Saturday Evening Post, Donovan told him, reflected a shift in American attitudes toward the Cuban revolution in the aftermath of the missile crisis. The average citizen, Donovan said, didn't want Cuba to become a Soviet satellite, 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." Once the prisoner exchange was completed, Donovan argued, Washington and Havana could turn to bigger and more important issues. Castro conceded that holding the Americans as "a bargaining asset" was not in Cuba's interest because "perhaps it's preventing something more constructive from being accomplished." Castro promised that "I'll release all of them to you" on April 22.

Their talks evolved into the very first serious conversation between Castro and a U.S. representative about how to normalize relations. Fidel posed the question: "If relations were to commence between the U.S. and Cuba how would it come about and what would be involved?" In his debriefing with the CIA, Donovan recounted his colorful response to Castro: "Are you familiar with porcupines? 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.' "

Common Sense Diplomatic Discussions

More than half a century later, Donovan's prediction finally became a reality. Drawing on the legacy of Donovan's ‘common sense' approach to negotiating with Cuba, the Obama administration quietly, and "very carefully" held back-channel talks with representatives of Raúl Castro, arriving at an "accommodation of views" to, once again, swap prisoners—three Cuban spies imprisoned in the U.S. since 1998 for a CIA mole and a USAID contractor imprisoned in Cuba—and then move toward normalized bilateral relations. Both presidents simultaneously announced the historic rapprochement on December 17, 2014.

Fidel Castro gave James Donovan this humidor after negotiations to free the Bay of Pigs prisoners.
Fidel Castro gave James Donovan this humidor after negotiations to free the Bay of Pigs prisoners.

Before Obama left the White House, Washington and Havana were able to fully restore diplomatic relations, reopen embassies, initiate direct mail services and direct commercial air routes, as well as significantly expand economic, cultural and political interaction. In his very last days as president, Obama took steps to normalize migration between the two nations, and sent his top negotiator, deputy national security advisor Benjamin Rhodes, to Havana to sign a new bilateral agreement on counterterrorism, counternarcotics and money laundering prevention programs, among other collaborative law-enforcement operations.

The Donovan-Castro talks not only set a historic foundation for the normalization of relations, they also provided historical lessons for successful dialogue and negotiations with Cuba. Unlike the Tractors for Freedom Committee, which imperiously sought to bully Castro into an agreement, Donovan approached the Cuban leader with respect and civility, along with a persistence, candor and true commitment to discourse. "This is work requiring great patience," he told The Nation. The profile in the magazine described Donovan as the "most successful American practitioner of metadiplomacy—higher diplomacy"—with Cuba.

"He used the art of negotiation as his weapon of choice," Donovan's daughter, Mary Ellen Fuller, recounted in Time magazine when Bridge of Spies premiered in 2015. "He felt that a person simply wants to be respectfully heard, and that it is only when you listen well that you can reach the most just results. History taught him that," she concluded, "and we could stand to use this weapon today." 

Peter Kornbluh writes frequently for Cigar Aficionado on Cuba.

"Great article, by the way!" —May 25, 2017 11:57 AM
"The quote has been corrected. Thanks for alerting us. " —May 22, 2017 17:24 PM
"The St. Francis Prayer is sadly misquoted here. It should read, "...Grant that I may not so much seek to be consoled as to console..." The key word being 'Not', which was omitted. That's essentially the point: Giving instead of Taking." —May 21, 2017 17:22 PM

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