During the nearly five decades Fidel Castro ruled Cuba, he survived CIA assassination attempts and a U.S. secret war of sabotage and intrigue.
But shortly before he died and with his brother Raúl still firmly in power, there was an abrupt pivot in U.S. Cuba policy — a rapprochement after 53 years of hostilities and a new era in U.S.-Cuba diplomatic relations.
“We will end an outdated approach that for decades has failed to advance our interests, and instead we will begin to normalize relations between our two countries,” President Barack Obama said in a surprise announcement on Dec. 17, 2014.
The thaw came after 18 months of secret high-level talks that included the intervention of Pope Francis, who offered the Vatican as a meeting place and sent personal letters to both Obama and Cuban President Raúl Castro beseeching them to find a solution to the plight of prisoners held in both nations and other matters.
Although the embargo remains in place, as part of the diplomatic breakthrough Obama also announced new rules to expand travel by Americans to the island, allow trade with private Cuban entrepreneurs and to partially revamp the U.S. financial relationship with Cuba.
Despite the renewed diplomatic ties, a deep political divide remains between the two countries.
Even though Fidel Castro often commented on world affairs and his nemesis to the north during his retirement, he was mute on the new relationship with the United States.
At times during the corrosive era of U.S.-Cuba relations he seemed to take an almost perverse pleasure in being the target of U.S. hostility.
President John F. Kennedy backed the CIA-financed Bay of Pigs invasion in 1961 while brother Robert and other members of his administration botched several attempts to assassinate Castro.
In a 2014 speech, Raúl said more than 600 plans to assassinate his brother had been hatched and that Cuba had endured “55 years of incessant struggle in the face of the designs of 11 U.S. administrations.”
Kennedy and Lyndon B. Johnson fought Fidel Castro’s efforts to export subversion throughout Latin America, while progressively tightening U.S. economic sanctions on Havana.
Johnson, responding to the growing domestic opposition to Castro with a generosity that perhaps benefited Castro more, later presided over the first two mass exoduses from the island — the Camarioca Boatlift and Freedom Flights that together brought 265,000 Cubans to the United States from 1965 to 1973.
Richard Nixon opened up China, but maintained a glacial stance toward Cuba.
At times, Castro seemed to go out of his way to keep bilateral relations on the front burner. Near the end of Gerald Ford’s tenure, Secretary of State Henry Kissinger opened secret negotiations with the Cubans, soon broken off as Havana began sending 36,000 troops to Angola.
A more friendly Jimmy Carter offered “reciprocal gestures,” including an exchange of diplomats just short of resuming full diplomatic relations, a fishing and maritime agreement, eased restrictions on U.S. travel to Cuba and the offer of U.S. visas for 3,900 political prisoners freed from Cuban jails.
But Carter was humiliated by the Mariel Boatlift of 1980, when Castro opened the doors to 125,000 Cubans who wanted to leave — and also hundreds of common criminals and mental patients who were all but ordered to leave.
Ronald Reagan used the Mariel fiasco in his first presidential campaign, blaming Carter for losing control of U.S. borders. Once in office, Reagan projected an image of anti-Communist toughness, often denouncing Cuba. However, aides were secretly authorized to improve relations with Havana, and in 1981 Secretary of State Alexander Haig was dispatched to Mexico to meet secretly with then-Cuban Vice President Carlos Rafael Rodríguez. The attempts for improved relations eventually went nowhere.
Meanwhile, the Miami's exile community’s political influence grew under the leadership of Jorge Mas Canosa, founder of the Cuban American National Foundation. With his appointment by Reagan as chairman of the Radio Martí advisory board, Mas gained entry into the White House, receiving official and often sensitive information on the administration’s dealings with Cuba.
Mas sealed the exile community’s influence over U.S. policy toward Havana by joining forces with Cuban Americans in Congress, including Miami Republicans Ileana Ros-Lehtinen and Lincoln Díaz-Balart.
George H.W. Bush watched communism collapse in Europe and appeared content to wait for the Castro regime to crumble from economic hardship and internal dissent. But exiles demanded new U.S. steps to hasten the demise — and got the Cuban Democracy Act of 1992, a law that for the first time since the early 1960s tightened U.S. economic sanctions on the island.
To the surprise of some Democrats, Bill Clinton adopted a “two-track” policy, continuing to enforce the act while at the same time authorizing higher levels of humanitarian relief by nongovernmental organizations and more “people-to-people contacts” in hopes of helping non-government players in Cuba.
The U.S. policy of increasing contacts with ordinary Cubans by phone, mail and visits led many to speculate that Clinton — who had opened up Vietnam and was expanding U.S. contacts with China — was preparing to lift U.S. sanctions on Cuba, perhaps early in a second administration.
But that possibility was dashed in 1996 when Cuban MiG fighters shot down two unarmed planes of Miami-based Brothers to the Rescue, killing all four aboard.
Amid a U.S. outcry in an election year, Clinton announced he would accept the Helms-Burton bill, another draconian tightening of U.S. sanctions that the president had long opposed.
The hostile tone lingered through the first George W. Bush administration, despite massive sales of U.S. food products to Cuba following Hurricane Michelle’s devastation in 2001. Even as Castro was vowing that cash deals would be a “one-time” purchase, and later that he would not buy “one grain of rice” from U.S. companies unless Washington extended credit for the purchases, America became the largest supplier of food products to Cuba.
U.S.-Cuban relations nevertheless hardened after Castro’s jailing of 75 dissidents during the Black Spring crackdown in 2003. That summer, Bush, heading into a re-election campaign and under mounting pressure from Cuban exiles in politically critical Florida, announced tough new measures against Cuba.
He ordered a tightening of the restrictions on U.S. travel to Cuba, even as the House and Senate, reflecting the significant shift in U.S. public opinion since the collapse of communism, voted strongly in favor of easing sanctions.
Bush’s threat of a veto killed the moves to ease the sanctions, and the president promised no change in U.S. policy until Cuba moved toward democracy.
At an Oct. 10, 2003, White House gathering with Cuban-Americans, Bush announced the creation of a Cabinet-level government commission “to plan for the happy day when Castro's regime is no more.”
Obama is the 11th U.S. president to face a communist Cuba.