Back Channel to Cuba

Back Channel to Cuba Plot Summary

Introduction

In April 1963, during negotiations over American prisoners held in Cuban jails, James Donovan, the American negotiator, was asked by Fidel Castro how relations between their countries might improve. Donovan replied with a metaphor that would define decades of diplomacy: "Do you know how porcupines make love? Very carefully." This cautious approach characterized the complex dance between Washington and Havana for over half a century. While most people are familiar with the public history of hostility between the United States and Cuba—the Bay of Pigs invasion, the Cuban Missile Crisis, the trade embargo—few know about the persistent efforts at dialogue that have run parallel to this antagonism. Every American president since Eisenhower has engaged in some form of secret communication with the Castro regime. These back-channel negotiations reveal a more nuanced relationship than the public rhetoric suggests, one where pragmatism often competed with ideology, and where both nations repeatedly sought ways to coexist despite their profound differences. For historians, diplomats, and anyone interested in how adversaries communicate during times of tension, this hidden history offers valuable insights into the complex interplay between public posturing and private problem-solving.

Chapter 1: Early Confrontation: Revolution to Missile Crisis (1959-1962)

When Fidel Castro's revolutionary forces marched into Havana on January 1, 1959, the Eisenhower administration faced a dilemma. The United States had long dominated Cuban affairs, with American businesses controlling much of the island's economy. Initially, Washington adopted a wait-and-see approach, dispatching Ambassador Philip Bonsal to establish a working relationship with the new revolutionary government. Early meetings between Castro and American officials were cordial, if cautious. The relationship deteriorated rapidly throughout 1959 as Castro implemented radical land reform, nationalizing American-owned properties without immediate compensation. When Vice President Richard Nixon met privately with Castro during his April 1959 visit to the United States, he came away convinced that Castro was "either incredibly naive about communism or under communist discipline." By summer 1959, the Eisenhower administration had begun shifting toward a policy of undermining the Castro regime, with the CIA developing plans for covert operations against Cuba. The final break came in early 1961 when Eisenhower severed diplomatic relations entirely, just before leaving office. The Kennedy administration inherited both the broken relationship and a planned invasion of Cuba. Despite misgivings, Kennedy approved the Bay of Pigs operation in April 1961, which ended in a humiliating defeat for the United States. This fiasco further radicalized Castro's revolution and cemented Cuba's alliance with the Soviet Union. Kennedy responded with Operation Mongoose, a covert program aimed at overthrowing Castro through sabotage, psychological warfare, and assassination attempts. The hostility culminated in the October 1962 Cuban Missile Crisis, when U.S. intelligence discovered Soviet nuclear missiles being installed in Cuba. For thirteen days, the world stood on the brink of nuclear war. The crisis was resolved when Soviet Premier Khrushchev agreed to withdraw the missiles in exchange for Kennedy's public pledge not to invade Cuba and a secret promise to remove U.S. missiles from Turkey. This near-catastrophe demonstrated the dangers of the confrontational approach and prompted both superpowers to establish a hotline to prevent future misunderstandings. The missile crisis marked a turning point. Though public hostility continued, it created an opening for secret diplomacy. In November 1962, James Donovan negotiated the release of Bay of Pigs prisoners, and UN Ambassador William Attwood initiated exploratory talks about normalizing relations. These early efforts at dialogue, though ultimately unsuccessful, established a pattern of secret negotiations that would continue for decades, revealing how even the most bitter adversaries could find ways to communicate when necessary.

Chapter 2: Kennedy's Secret Initiatives and Johnson's Pragmatism (1963-1968)

The period following the missile crisis saw the first serious attempts at secret diplomacy between the United States and Cuba. In the aftermath of the crisis, President Kennedy began to reconsider the hostile approach to Cuba. Through intermediaries like journalist Lisa Howard and UN diplomat William Attwood, Kennedy explored the possibility of a rapprochement with Castro. These efforts gained momentum in the fall of 1963, with plans for secret talks in Havana. Kennedy authorized Attwood to establish a secret channel with Castro's aide Rene Vallejo. Kennedy told Attwood he was ready to begin a dialogue with Cuba, but emphasized the need for absolute secrecy due to domestic political considerations. Tragically, Kennedy's assassination in November 1963 occurred just as these tentative contacts were developing. When journalist Jean Daniel, who had met with Kennedy, was with Castro when news of the assassination broke, Castro reportedly said: "This is bad news... Now, everything is going to change." President Johnson initially continued these secret contacts, but the momentum for dialogue soon dissipated. Johnson was more focused on Vietnam and domestic issues, while Castro became increasingly involved in supporting revolutionary movements in Latin America and Africa. The CIA's covert operations against Cuba continued, and in 1964, the Organization of American States imposed multilateral sanctions against Cuba at U.S. urging. Despite this hostile environment, practical issues forced limited cooperation. In 1965, the two countries negotiated the "Freedom Flights" program allowing Cubans with relatives in the U.S. to emigrate legally. This airlift program eventually brought over 260,000 Cubans to America between 1965 and 1973. Though limited in scope, it represented the first successful bilateral agreement between the hostile neighbors and established a precedent for cooperation on migration issues. By 1968, the relationship had settled into a pattern of hostility and mutual suspicion that would persist for decades. Yet even during this period, Johnson authorized renewed secret contacts. In July 1968, his administration lifted the ban on American companies selling food and medicines to Cuba through their foreign subsidiaries. This modest step suggested a potential thaw, but the Soviet invasion of Czechoslovakia in August 1968 and Castro's public support for it dampened enthusiasm in Washington for further engagement. The Kennedy and Johnson years established important patterns in U.S.-Cuba secret diplomacy: the use of trusted intermediaries, the focus on practical issues like migration, and the vulnerability of dialogue to external events and domestic politics. Though full normalization remained elusive, these early covert channels laid groundwork for future negotiations and demonstrated that even amid public hostility, private diplomacy was possible.

Chapter 3: Nixon-Ford Era: Kissinger's Caribbean Détente Attempt (1974-1976)

The early 1970s witnessed the first serious high-level attempt to normalize relations since the Cuban Revolution. This initiative was driven primarily by Henry Kissinger, who served as National Security Advisor and later Secretary of State under Presidents Nixon and Ford. Kissinger believed that the isolation of Cuba had become counterproductive, especially as other Latin American countries began reestablishing relations with Havana. In 1974, following Nixon's resignation, Kissinger quietly authorized exploratory talks with Cuban representatives. The secret channel was established through Frank Mankiewicz, a journalist with connections to both governments. Mankiewicz delivered a verbal message from Kissinger to Castro expressing interest in beginning a dialogue. Castro responded positively, sending a handwritten note back through the same channel. This exchange led to formal secret meetings in early 1975, with State Department official William Rogers meeting Cuban diplomat Ramón Sánchez-Parodi at LaGuardia Airport and later at a safe house in New York. As a gesture of good faith, the Ford administration lifted some sanctions against Cuba in August 1975, allowing U.S. subsidiaries in third countries to trade with Cuba and removing penalties for other nations that did business with the island. The administration also quietly authorized limited charter flights between the countries and eased restrictions on travel by academics and journalists. Throughout the summer of 1975, both sides made goodwill gestures. The United States voted to lift OAS sanctions against Cuba, while Cuba returned $2 million in ransom money from a 1972 airline hijacking and allowed the parents of baseball pitcher Luis Tiant to emigrate to the United States. However, this promising diplomatic opening collapsed in late 1975 when Cuba sent troops to Angola to support the left-wing MPLA movement fighting for control after Portuguese colonial rule ended. Kissinger viewed this intervention as Cuban expansionism backed by the Soviet Union, making further normalization politically impossible. President Ford declared that Cuba's military intervention "destroys any opportunity for improvement of relations with the United States." By early 1976, Kissinger had shifted from dialogue to planning potential military action against Cuba. The failure of Kissinger's initiative demonstrated the fundamental tension in U.S.-Cuban relations: Washington expected Cuba to accommodate American interests as the price of normalization, while Havana insisted on being treated as a sovereign equal. As Castro later explained: "What we do not accept are humiliating conditions—the absurd price which the United States apparently would have us pay for an improvement in relations." Despite this failure, the Nixon-Ford period established important precedents for future negotiations and showed that practical cooperation was possible even amid ideological conflict.

Chapter 4: Carter's Bold Outreach and African Complications (1977-1980)

Jimmy Carter brought a fresh approach to Cuba policy when he entered the White House in 1977. Unlike his predecessors, Carter believed in engaging adversaries and prioritized human rights in foreign policy. Just weeks after his inauguration, he signed Presidential Directive NSC-6, ordering his administration to "attempt to achieve normalization of our relations with Cuba" through "direct and confidential talks." Carter quickly took confidence-building measures: suspending reconnaissance flights over Cuba, lifting the travel ban, and allowing cultural exchanges. The Cubans reciprocated by releasing political prisoners and easing restrictions on Cuban American visits. In March 1977, the two countries signed agreements on fishing rights and maritime boundaries, and in May they agreed to establish Interests Sections in each other's capitals—diplomatic outposts that fell short of embassies but allowed for direct communication. However, Carter's foreign policy team was divided on Cuba. Secretary of State Cyrus Vance favored normalization, while National Security Advisor Zbigniew Brzezinski was skeptical. This division became critical when Cuba deployed troops to Ethiopia in late 1977 to help repel a Somali invasion. Brzezinski saw this as proof of Cuba's role as a Soviet proxy and pressed Carter to make withdrawal of Cuban troops from Africa a precondition for improved relations. Castro insisted that Cuba's foreign policy was not negotiable, creating an impasse that complicated normalization efforts. Despite these tensions, secret talks continued. Between April 1978 and December 1979, U.S. and Cuban officials held six rounds of confidential discussions. The breakthrough moment came in November 1978 when Castro met with a group of Cuban exiles led by banker Bernardo Benes. Castro agreed to release 3,600 political prisoners and allow family visits by Cuban Americans. The first such visits occurred in December 1978, reuniting families separated for nearly two decades. By summer 1979, relations had improved enough that U.S. and Cuban officials held secret talks about establishing full diplomatic relations. The final blow to normalization came in 1980 with the Mariel boatlift crisis. When thousands of Cubans sought asylum at the Peruvian Embassy in Havana, Castro announced that anyone who wanted to leave could do so through the port of Mariel. Over 125,000 Cubans fled to Florida, creating a humanitarian and political crisis that damaged Carter politically. The Soviet invasion of Afghanistan in December 1979 had already chilled U.S.-Soviet relations, making improved ties with Cuba politically impossible. Carter later reflected that he missed an opportunity: "It may be that we overemphasized the need for Cuba to make a dramatic break with the Soviet Union in Ethiopia. I think in retrospect, knowing what I know since I left the White House, I should have gone ahead and been more flexible in dealing with Cuba and established full diplomatic relations." Defeated for reelection by Ronald Reagan, Carter had no second chance to normalize relations.

Chapter 5: Reagan-Bush: From Hostility to Limited Cooperation (1981-1992)

The Reagan administration began with unprecedented hostility toward Cuba. Secretary of State Alexander Haig reportedly told Reagan, "You just give me the word, and I'll turn that island into a parking lot." Reagan considered military action against Cuba but was dissuaded by advisors who warned that the well-trained Cuban army could turn the country into "another Vietnam." Instead, Reagan tightened the embargo, restricted travel, and launched Radio Martí to broadcast anti-Castro programming to the island. Despite this public hostility, pragmatic considerations led to quiet cooperation on specific issues. The 1984 migration agreement, negotiated through the good offices of Mexican President Miguel de la Madrid, restored orderly immigration procedures after the chaos of the Mariel boatlift. Cuba agreed to accept the return of 2,746 "excludables" from the Mariel exodus, while the United States committed to issue up to 20,000 immigrant visas annually to Cubans. Regional conflicts provided another arena for tactical dialogue. In 1981-82, Cuba repeatedly approached the Reagan administration seeking talks on Central America, where Cuban-supported insurgencies were fighting U.S.-backed governments. Though Reagan initially rejected these overtures, by 1984 the administration engaged in secret talks with Cuban officials in Mexico City. These discussions, led by U.N. Ambassador Vernon Walters, focused on coordinating the withdrawal of Cuban troops from Angola with South African withdrawal from Namibia. The most surprising development came in 1987-88, when Cuba and the United States worked together to negotiate the withdrawal of Cuban troops from Angola and the independence of Namibia. Assistant Secretary of State Chester Crocker led fourteen rounds of negotiations involving Cuba, Angola, South Africa, and the United States. The resulting December 1988 accords represented a diplomatic triumph that earned praise even from Reagan's hardliners. As Crocker observed, Castro had "the clearest strategy of any of the parties" and his determination to reach an agreement "pulled [the Angolans] along in his wake." The George H.W. Bush administration, which took office in 1989, faced a dramatically changing international landscape as the Cold War ended. The collapse of the Soviet Union left Cuba economically vulnerable and strategically isolated. Rather than seizing this opportunity for dialogue, Bush calculated that Castro's regime might soon collapse and therefore maintained a policy of isolation and pressure. When Soviet subsidies to Cuba ended in 1991, Bush tightened sanctions further through the Cuban Democracy Act, confident that economic pressure would hasten Castro's downfall. Throughout this period, the fundamental contradiction in U.S. policy remained unresolved: Washington sought Cuba's cooperation on specific issues while simultaneously trying to isolate and undermine the Castro regime. This contradiction would continue to shape relations through subsequent administrations, demonstrating how difficult it was to escape patterns of hostility once established, even when practical cooperation proved possible on specific issues.

Chapter 6: Clinton's Calibrated Engagement and Missed Opportunities (1993-2000)

Bill Clinton entered office in 1993 with a personal understanding that the embargo was "counterproductive," yet politically he recognized the need to appeal to Cuban American voters in Florida. During his campaign, Clinton endorsed the Cuban Democracy Act, which tightened the embargo but also authorized increased people-to-people contact and humanitarian assistance. This dual approach of maintaining pressure while allowing limited engagement characterized Clinton's entire Cuba policy. In his first year, Clinton took modest steps to reduce tensions: declaring that the United States posed "no military threat" to Cuba, prosecuting exile groups planning attacks on the island, and expanding licenses for humanitarian, religious, and educational travel. The Cubans reciprocated by releasing political prisoners and easing travel restrictions for Cuban Americans. The administration developed what it called a policy of "calibrated response"—a strategy of responding positively to Cuban reforms while maintaining pressure. This cautious engagement was tested in August 1994 when thousands of Cubans took to the sea on makeshift rafts, creating a migration crisis. Clinton responded by ordering the Coast Guard to intercept the rafters and detain them at Guantánamo Bay Naval Base. To resolve the crisis, the administration engaged in secret negotiations with Cuba through multiple channels, including former President Jimmy Carter and Mexican President Carlos Salinas. These talks resulted in a September 1994 migration accord in which Cuba agreed to prevent unsafe departures and the United States committed to providing at least 20,000 visas annually to Cuban immigrants. The diplomatic momentum was shattered in February 1996 when Cuban fighter jets shot down two civilian planes operated by Brothers to the Rescue, an exile group that had repeatedly violated Cuban airspace. Clinton responded by signing the Helms-Burton Act, which codified the embargo into law and removed the president's authority to lift sanctions without congressional approval. This legislation severely limited Clinton's flexibility in dealing with Cuba for the remainder of his presidency. Despite this setback, Clinton pursued a "parallel positive steps" approach in his second term. His administration expanded people-to-people contacts through academic, cultural, and religious exchanges. In January 1999, Clinton announced measures to increase direct flights to Cuba, expand remittances, and authorize food and medicine sales. The administration also facilitated baseball diplomacy, with the Baltimore Orioles playing the Cuban national team in Havana and Baltimore. More significantly, Clinton authorized unprecedented cooperation on counter-narcotics and counterterrorism issues, with Cuban and American officials meeting regularly to coordinate drug interdiction efforts. The most dramatic test of Clinton's Cuba policy came in late 1999 when Elián González, a six-year-old Cuban boy, was rescued at sea after his mother drowned attempting to reach Florida. The ensuing custody battle between the boy's father in Cuba and relatives in Miami became an international incident. Clinton's decision to return Elián to his father in Cuba angered many Cuban Americans but demonstrated his willingness to make politically difficult decisions when legal principles were at stake. By the end of Clinton's presidency, U.S.-Cuban relations remained formally hostile, but increased people-to-people contact had created new channels of communication and understanding. Clinton had not normalized relations, but he had laid groundwork for a more engaged approach that recognized the value of direct contact between the American and Cuban people, even as the fundamental political impasse remained unresolved.

Chapter 7: Obama's Path to Normalization: Breaking the Diplomatic Ice (2009-2016)

Barack Obama campaigned on a promise to engage with Cuba, arguing that fifty years of isolation had failed to achieve U.S. objectives. After winning the 2008 election with unprecedented support from younger Cuban Americans, Obama began implementing incremental changes. In April 2009, he lifted all restrictions on family travel and remittances. At the Summit of the Americas, he declared: "I'm prepared to have my administration engage with the Cuban government on a wide range of issues—from drugs, migration, and economic issues, to human rights, free speech, and democratic reform." Behind the scenes, more significant diplomatic engagement was underway. The administration restored migration talks suspended by Bush and expanded cooperation on environmental issues, disaster response, and counter-narcotics efforts. When the Deepwater Horizon oil spill threatened both countries in 2010, American and Cuban scientists worked together on prevention and response measures. The Coast Guard established regular communication with Cuban authorities to coordinate search and rescue operations. A major obstacle to further progress emerged when Cuba arrested USAID contractor Alan Gross in December 2009 for distributing satellite communications equipment to Cuban Jewish communities. The administration sent numerous emissaries, including former President Jimmy Carter and New Mexico Governor Bill Richardson, to seek Gross's release, but Cuba insisted on exchanging him for five Cuban intelligence officers imprisoned in the United States. This impasse effectively paralyzed Obama's Cuba policy for several years. The breakthrough came in 2013 when Obama authorized secret talks with Cuba, held in Canada and facilitated by Pope Francis and the Vatican. These negotiations, led by Ben Rhodes and Ricardo Zúñiga for the United States and Alejandro Castro Espín (Raúl Castro's son) for Cuba, addressed a range of issues including the release of prisoners, establishing diplomatic relations, and easing economic restrictions. After eighteen months of confidential talks, Obama and Raúl Castro simultaneously announced the restoration of diplomatic relations on December 17, 2014. The agreement included a prisoner exchange: Cuba released Alan Gross and a U.S. intelligence asset, while the United States freed the remaining three members of the "Cuban Five" intelligence officers. Obama also announced his intention to review Cuba's designation as a state sponsor of terrorism and to ease restrictions on travel, commerce, and financial transactions. In May 2015, the State Department removed Cuba from the list of state sponsors of terrorism, and in July, diplomatic relations were formally restored with the reopening of embassies in Washington and Havana. Obama's historic visit to Cuba in March 2016 – the first by a sitting U.S. president since Calvin Coolidge in 1928 – symbolized the transformation in relations. During his visit, Obama met with Raúl Castro, addressed the Cuban people directly in a televised speech, attended a baseball game between the Tampa Bay Rays and the Cuban national team, and met with Cuban dissidents. The normalization process yielded tangible results: direct commercial flights resumed between the United States and Cuba; American companies like Airbnb, Starwood Hotels, and Google established operations on the island; and bilateral cooperation expanded in areas such as environmental protection, law enforcement, and health research. Yet significant obstacles remained. The embargo, codified into law by Helms-Burton, could only be lifted by Congress, which showed no inclination to do so. The Cuban government, while welcoming improved relations, remained cautious about the pace and extent of economic and political reforms. Nevertheless, Obama's Cuba policy represented the most significant shift in U.S.-Cuban relations since the revolution, establishing a new framework that recognized the failure of isolation and emphasized the potential benefits of dialogue and cooperation.

Summary

The hidden history of U.S.-Cuba diplomatic negotiations reveals a persistent undercurrent of pragmatism beneath the surface of public hostility. From Kennedy's secret outreach after the missile crisis to Carter's comprehensive normalization effort, from Reagan's migration agreement to Clinton's counterterrorism cooperation, and finally to Obama's historic breakthrough, both nations have repeatedly found ways to communicate and cooperate despite seemingly irreconcilable differences. Throughout six decades of official hostility, every administration engaged in some form of dialogue with the Castro regime, recognizing that certain issues required cooperation regardless of ideological differences. The central tension throughout this history was between Cuba's demand for respect and sovereignty versus America's expectation that better relations should constrain Cuban behavior. Time and again, negotiations faltered when the United States tried to dictate Cuba's foreign policy or internal affairs. Yet the record also shows that when both sides approached talks with mutual respect and realistic expectations, tangible agreements could be reached on issues like migration, hijacking, and maritime boundaries. This diplomatic history offers important lessons for international relations more broadly. First, it demonstrates that diplomatic engagement need not imply approval of another government's policies but can serve practical national interests. Second, it reveals how domestic politics often constrains foreign policy options, as seen when electoral considerations repeatedly derailed promising diplomatic initiatives. Finally, it shows that effective diplomacy requires patience, creativity, and a willingness to understand the other side's core interests and constraints. As nations continue to navigate complex rivalries in the twenty-first century, the U.S.-Cuba experience stands as both a cautionary tale about the costs of diplomatic failure and an encouraging example of how persistent engagement can eventually overcome decades of hostility.

About Author

Loading...

William M. Leogrande

Read more