Ten years ago this month, the United States and Cuba reached a historic deal to normalize diplomatic relations, which was intended to end decades of acrimonious conflict between the two countries and bring prosperity to Cuba. Instead, relations today are at a low point, and Cuba is facing one of the worst economic crises in its history. What went wrong? How is it that a dramatic foreign-policy initiative—one as momentous as U.S. President Richard Nixon’s opening to China and broadly supported by the American people and U.S. allies around the world—failed to establish what President Barack Obama called “a new chapter” in the tormented history of U.S.-Cuba relations?
It began auspiciously. On Dec. 17, 2014, Obama and Cuban President Raúl Castro stunned the world with their simultaneous televised announcement that the United States and Cuba had agreed to restore ties. “Today, America chooses to cut loose the shackles of the past so as to reach for a better future—for the Cuban people, for the American people, for our entire hemisphere, and for the world,” Obama announced. Within the privacy of the Oval Office he was even more effusive, declaring, “As Joe Biden would say, this is a big fucking deal.’”
And so it was. After more than 50 years of perpetual hostility in U.S. policy toward Cuba—dominated by dangerous Cold War episodes such as the Bay of Pigs invasion, the Cuban missile crisis, CIA assassination plots, terrorist exile violence, and the enduring U.S. trade embargo—the rapprochement between Washington and Havana marked a historic foreign-policy achievement. In short order, Havana and Washington reopened embassies, normalized U.S. travel, expanded trade and commerce, and began collaborating on key areas of mutual interest. In March 2016, Obama became the first sitting U.S. president to travel to Havana since 1928. “I have come here to bury the last remnant of the Cold War in the Americas,” Obama declared in his address to the Cuban people. “The path we are on will continue beyond my administration,” he predicted in a press conference with Raúl Castro.
Obama’s optimism proved to be wrong. During the Trump administration, the historic opening to Havana was all but closed. One by one, President Donald Trump rescinded Obama’s executive authorizations on travel and commerce, replacing them with a slew of new, punishing sanctions—penalties that remained largely unaltered during Joe Biden’s presidency.
Now, the euphoria and economic dynamism generated by the agreement are long gone. The Cuban economy has all but collapsed, stricken by massive shortages of food, medicine, fuel, and electricity that have created a dire humanitarian crisis for the populace. Those who can are leaving the island in droves; those who can’t are suffering widespread deprivation. Ten years after the high hopes generated by rapprochement, many Cubans are experiencing a profound sense of hopelessness for the future.
And the worst may be yet to come. With Trump’s reelection in the 2024 presidential election, and his nomination of hardliner Sen. Marco Rubio for secretary of state, Cuba faces a return to the Cold War-era of regime-change intervention. As tensions mount in the months ahead, the 10th anniversary of rapprochement serves as a reminder that there is a productive alternative to a posture of hostility and regime change—one that ought to appeal to a president determined to reduce irregular migration, blunt the hemispheric influence of China and Russia, and avoid pointless foreign conflicts.
The Cuba Détente
Obama talks to tourists and Cubans at Havana Cathedral on March 20, 2016. Yamil Lage/AFP via Getty Images
The history-making accord between the United States and Cuba was a product of political courage and a tenacious commitment to creative diplomacy on both sides. The courage belongs mostly to Obama, who was determined to address an intractable foreign-policy challenge that had bedeviled many of his predecessors. Secretary of State Henry Kissinger, President Jimmy Carter, and President Bill Clinton all demanded quid pro quos in secret talks to improve relations with the Castro regime, whereas Obama chose “to play the long game with Cuba,” according to Richard Feinberg, former senior director of inter-American affairs at the National Security Council (NSC). Instead of demanding concessions, Obama exercised strategic patience in moving unilaterally to normalize bilateral ties, calculating that closer cultural, political, and economic relations would eventually result in meaningful reforms on the island.
In early 2013, Obama tasked his deputy national security advisor, Benjamin Rhodes, to open a back channel to Cuba with the goal of fundamentally changing the future of U.S.-Cuban relations. Astutely, Obama decided to avoid incremental steps and instead pursue a diplomatic full Monty. “If I’m going to do this, I want to do as much as we can all at once,” he instructed Rhodes.
The ultra-secret diplomacy between Washington and Havana took place during furtive meetings in Canada, Trinidad and Tobago, and, finally, at the Vatican in Rome. Rhodes and Ricardo Zuñiga, who was a senior director for Western Hemisphere affairs at the NSC at the time, represented Obama; Raúl Castro assigned his son, Maj. Alejandro Castro and another military officer. Over the course of 18 months, the two sides negotiated both a prisoner exchange—swapping Alan Gross, a subcontractor for the U.S. Agency for International Development and a high-level CIA mole captured in Cuba, for three Cuban espionage agents who were part of the “Cuban Five” spy network and incarcerated in the United States since 1998—and the process for normalizing relations. On Dec. 16, President Obama placed a direct call to Raúl Castro from the Oval Office to finalize details of the deal. “There was a sense of history in that room,” recalled Zuñiga, who was present.
In Cuba, Dec. 17, 2014, is known as diez y siete d—the iconic day of 17-D. By coincidence, we were both in Havana at an annual conference on U.S.-Cuban relations when news of the dramatic breakthrough broke. Public euphoria was instantaneous. People flooded into the streets, car horns blared, and church bells rang. Waiters and busboys shook our hands, gave us high-fives and even hugs. “I am finally going to be able to buy a new Ford van,” exclaimed one driver of the vintage American cars that provide taxi services in Cuba, summing up the hopes of the Cuban people for a better future.
In their televised presentations, the two presidents outlined the contours of a new relationship. As a humanitarian gesture, Cuba agreed to release 53 political prisoners and engage with the International Red Cross and United Nations on human rights and prison conditions. Obama pledged to review Cuba’s designation as a state sponsor of terrorism and to loosen restrictions on travel and trade. Both countries agreed to formally reinaugurate their embassies, which were closed when President Dwight D. Eisenhower’s administration broke diplomatic ties with Cuba in January 1961, but reopened as interest sections during the Carter administration.
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Obama reaches down through a protective net and over a wall to shake hands with Luis Tiant. Castro is next to Obama in the stands of a baseball stadium. - Obama and Cuban President Rául Castro greet baseball player Luis Tiant at an exhibition game between the Cuban national team and the Tampa Bay Rays in Havana on March 22, 2016. Joe Raedle/Getty Images
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A crowd of baseball fans sit in the stand. Several hold up cell phones to take pictures. - Fans cheer as Obama and Castro arrive for the exhibition baseball game in Havana on March 22, 2016. Nicholas KammAFP via Getty Images
The process of normalization moved quickly. After an official review, the White House removed Cuba from the State Department list of state sponsors of international terrorism in 2015, and both countries officially reopened their embassies that summer. As he prepared for his historic trip to Havana in March 2016, Obama significantly loosened travel restrictions on visiting the island, allowing individual travelers to go under the broad people-to-people category. To facilitate travel, the administration resumed regular commercial air service; for the first time in over half a century, travelers could fly to Cuba on U.S. carriers such as American Airlines, Delta, United, and JetBlue. Obama also authorized U.S. cruise ships to port in Cuban harbors. “We have enormous confidence in the American people as ambassadors for the things that we care about,” Rhodes said at the time. “We believe that’s the best way to connect the Cuban people with the wider world.”
Positive Engagement: A Success Story
Tourists take in the sites from a double-decker tour bus of Havana on Feb. 28, 2015.Joe Raedle/Getty Images
The honeymoon of détente with Cuba lasted just over two years. But even in that short time, it produced measurable results. Although hardliners, led by Rubio and former Sen. Robert Menendez, attacked Obama for failing to negotiate the capitulation of the Cuban government, the brief era of reconciliation was overwhelming successful by any reasonable standard of foreign-policy objectives.
To expand cooperation on areas of mutual strategic and international interests, Washington and Havana established a bilateral commission to oversee the work of 18 diplomatic working groups, including ones on national security issues like migration, counternarcotics, and counterterrorism. Two of the groups also began discussions on contentious issues: human rights and property claims.
Relaxing travel restrictions allowed U.S. residents to see Cuba for themselves. During the first year of normalization, the number of U.S. visitors to Cuba rose from 92,000 to 163,000; after Obama restored commercial air service and authorized cruise ships to include Cuban ports of call, the floodgates of U.S. travel to Cuba opened and the numbers rose exponentially. In addition to 517,000 Cuban Americans who visited family in 2016, more than 600,000 other U.S. travelers set foot on the island in 2016 and 2017 before Trump’s travel restrictions took effect.
The influx of U.S. travelers provided an immediate boost to the Cuban economy, particularly the fledgling private sector. The number of Cuban entrepreneurs catering to tourists—taxi drivers, restaurateurs, tour guides, artists, musicians, and private hotel owners, among others—exploded overnight. Airbnb rentals illustrate the dramatic financial impact. In 2015, when Obama authorized Airbnb to begin working with private Cuban homeowners who wanted to rent rooms to U.S. visitors, the site recorded some 2,000 bookings; by 2019, that number had risen to 35,000. Cuba became one of Airbnb’s fastest-growing markets, vastly expanding job opportunities for homeowners, cooks, housecleaners, painters, carpenters, drivers, and guides. During Obama’s trip to Havana in March 2016, a Republican member of his business entourage, former Secretary of Commerce Carlos Gutierrez, characterized Obama’s strategy as “a great journey of human rights” because it advanced the cause of individual economic independence and the freedom for Cubans “to develop their own future, their own vision for their life.”
Obama’s entourage also included high-profile executives from Airbnb, PayPal, and Marriott, among other corporate representatives. Along with Obama, they met with many Cuban entrepreneurs, sending a clear signal of support for the private sector. “The embargo is going to end,” Obama predicted during a press conference with Raúl Castro. “This is a new day—es un nuevo día—between our two countries.”
The Trump Rollback
Cubans watch the TV broadcast of the inaugural ceremony of new U.S. President Donald Trump in Havana on Jan. 20, 2017. Yamil Lage/AFP via Getty Images
In the aftermath of Obama’s trip, White House officials optimistically believed that the process of normalizing U.S.-Cuba relations was not only successful—it was now “irreversible.” “The fact of the matter is that the American people and the Cuban people overwhelmingly want this to happen,” Rhodes said in June 2016. “For somebody to try to turn this off, they would have to be working against the overwhelming desires of their own people. That ship has sailed.”
To be sure, Obama’s opening to Cuba was immensely popular both at home and abroad. U.S. allies universally applauded it, Pope Francis blessed it, the Cuban people loved it, and the general U.S. public supported it, including more than half of Cuban Americans. Even an interagency review conducted during Trump’s first months in office concluded that Obama’s positive engagement was a foreign-policy success. But although engagement produced dramatic results, especially on the diplomatic front, two years was not long enough for it to put down roots. No significant domestic constituency, particularly influential U.S. business interests, developed enough of a stake in the policy to invest scarce political capital to defend it from Trump.
During the 2016 presidential campaign, Trump promised conservative Cuban Americans that he would dismantle Obama’s policy. On June 16, 2017, he repudiated normalization and resuscitated regime change, telling a cheering crowd in Miami, “Effective immediately, I am canceling the last administration’s completely one-sided deal with Cuba.” New regulations restricted travel, imposed limits on remittances, and blocked business with Cuban companies managed by the military, including most hotels. The diplomatic working groups on issues of mutual interest were disbanded.
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That fall, after several staff members at the U.S. Embassy in Cuba reported mysterious neurological symptoms (later dubbed Havana Syndrome), the State Department cut staffing to a skeleton crew and expelled most of the personnel at the Cuban Embassy in Washington. That limited diplomatic engagement to the bare minimum and halted visa processing, effectively ending cultural and educational exchanges.
In 2019, National Security Advisor John Bolton spearheaded a “maximum pressure” policy to cut off all foreign-exchange flows into Cuba. The administration eliminated people-to-people educational travel, prohibited visitors from staying in most hotels, and drastically cut air service. It disrupted Venezuelan oil shipments to Cuba by sanctioning the carriers and pressured Latin American countries to end their medical service contracts with Cuba. Trump activated Title III of the 1996 Cuban Liberty and Democratic Solidarity Act to deter foreign investors by threatening them with litigation in U.S. courts for profiting from nationalized property.
In its final months, the Trump administration limited family remittances from Cuban Americans and then forced Western Union to stop wiring remittances to the island. In a parting shot, just weeks before Biden’s inauguration, Trump put Cuba back on the State Department’s list of state sponsors of international terrorism, crippling Cuba’s ability to engage in international financial activity.
Together, these measures constituted the most severe sanctions since the embargo was imposed in the 1960s and cost the Cuban economy billions of dollars annually. Then came the COVID-19 pandemic. Beset by the structural problems typical of centrally planned economies and weakened by U.S. sanctions, the Cuban economy was like a patient with preexisting conditions. The tourism industry was closed for almost two years, with lost revenue of more than $6 billion. Family visits stopped, closing off the principal remaining channel for remittances, which fell from an estimated $3.7 billion in 2019 to $2.4 billion in 2020 and $1.1 billion in 2021. By the time Trump left office, Cuba was in crisis and few traces of Obama’s engagement policy remained.
Biden’s Half-Measures
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People wearing face masks gather on a street next to a large mural of Fidel Castro on a nearby building. - People line up to buy products with U.S. dollars at a store in Havana on July 20, 2020. Cuba eliminated the dollar tax to boost its economy amid the COVID-19 pandemic. Adalberto Roque/AFP via Getty Images
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A man wearing a shirt with Al Pacino on it, U.S. flag shorts, and a mask over his fae leans against a wall in a doorway. - A man wearing shorts with a U.S. flag design stands on a Havana street on May 3, 2021. During the pandemic, Cubans experienced the compound effects of the U.S. embargo and the absence of tourists. Yamil Lage/AFP via Getty Images
Biden’s election in 2020 seemed to promise some relief. During the campaign, he criticized the impact of Trump’s policies on Cuban families and promised to restore Obama’s policy of normalization “in large part.” But he never did. Domestic politics played a role, as it so often has in Cuba policy. Biden’s first chief of staff, Ron Klain, was a veteran of Al Gore’s narrow defeat in the 2000 presidential election, after Clinton returned 6-year-old Elián González to his father in Cuba. That ignited a firestorm in Miami’s Cuban American community and cost Gore the presidency. To Klain, Cuba remained the third rail of Florida politics. Biden’s personal style also played a role. On contentious issues, he liked to consult with former Senate colleagues. On Cuba, that was Menendez, who was chairman of the Foreign Relations Committee and also a fierce opponent of any engagement—his swing vote in the divided Senate was essential for Biden’s broader legislative agenda.
Under pressure from Latin America, Biden did offer some half-measures to forestall a boycott of the ninth Summit of the Americas in 2022. He eliminated limitations on remittances and partially restored people-to-people travel but kept the prohibition on staying in government hotels. After a two-year delay, he approved regulatory changes to help Cuba’s emerging private sector but left in place financial restrictions limiting its ability to take advantage of the new rules. Most importantly, he left Cuba on the list of state sponsors of terrorism, even though Secretary of State Antony Blinken admitted publicly, and Biden himself admitted privately, that it did not belong there.
The result has been an incoherent hybrid policy, with elements of engagement grafted onto Trump’s policy of regime change. As Biden’s era ends, there is little indication that he will use his lame-duck period to finally keep the Cuba-policy promises he made in 2020.
Trump Redux
A Trump 2024 flag is seen as people wave Cuban and U.S. flags during a rally against the Cuban government in Miami on July 17, 2021. Eva Marie Uzcategui/AFP via Getty Images
Trump’s return to the White House could presage a return to maximum pressure, especially with Rubio as secretary of states and Rep. Mike Waltz as national security advisor. Rubio and Republican Cuban Americans on the Hill will surely push for it, just as they did in Trump’s first term. They will point out that 70 percent of Cuban Americans in Florida voted for him and that a recent Florida International University (FIU) poll found 72 percent of Cuban American respondents support maximum pressure to promote regime change.
But resuming maximum pressure would stir a political hornet’s nest. After eight years of intense sanctions exacerbated by the Cuban government’s policy mistakes, the island is suffering an unprecedented economic and social crisis. Life is so hard and prospects for the future are so grim that more than a million Cubans—9 percent of the population—emigrated in the past three years. Three-quarters of them have come to the United States, 690,000 arrived undocumented at the southern border, another 100,000 admitted under Biden’s humanitarian parole program. If Trump adopts policies that deepen Cuba’s crisis, the new surge of migrants could dwarf these numbers, which would seriously complicate his plans to end irregular immigration.
Cuban Americans are not likely to support closing the southern border to Cuban migrants, and immigration law prohibits discrimination on the basis of nationality. If the administration tries to make an exception for Cubans, the policy will certainly be challenged in court. Trump’s plans to deport undocumented immigrants could face even bigger problems. Tearing recent Cuban migrants from their families, many of whom paid traffickers thousands of dollars to bring their relatives here, would cause a political firestorm in south Florida. The FIU poll found that 72 percent of respondents support humanitarian parole for Cuban migrants and that half are planning to bring relatives still in Cuba to the United States in the future.
In foreign policy, tougher Cuba sanctions would complicate relations with Mexico. President Claudia Sheinbaum is supporting Cuba by sending it cheap oil. In 2023, her predecessor, Andrés Manuel López Obrador, warned the Biden administration that Cuban migration spurred by U.S. sanctions was causing problems for Mexico and complicating cooperation with Washington on migration issues. Cooperation with Mexico, as Trump learned in his first term, is indispensable for limiting undocumented migration and narcotics trafficking across the southern border, which are all top priorities for him.
A car drives past the U.S. Embassy in Havana on March 18. Yamil Lage/AFP via Getty Images
Escalating sanctions on Cuba could also complicate Trump’s desire to improve relations with Russia. Moscow has grown closer with Havana in recent years, expanding relations beyond economic cooperation into a “strategic partnership,” as the two countries describe it. Cuba has defended Russia’s rationale for its invasion of Ukraine, making Havana a valuable ally in the Global South. And Russian President Vladimir Putin clearly values having an outpost in the United States “near abroad,” if only as a geopolitical thorn in Washington’s side. In short, Russia has a clear interest in the survival of the Cuban regime.
If sanctions succeed in destabilizing Cuba to the point that the state fails and social violence erupts, the pressure from Cuban Americans for U.S. military intervention will be immense. Cuban American elected officials demanded intervention in July 2021, in response to the Cuban government’s suppression of nationwide demonstrations, even though the largely peaceful protests only lasted a few days. U.S. intervention would poison relations with Latin America for a generation.
Trump is notoriously transactional. He promised Cuban Americans he would be tough on Cuba if they voted for him and they did, in near record numbers. But Trump is also notoriously self-interested, so if a policy of tightening the screws on Cuba will cause him major headaches in carrying out his immigration policy—the centerpiece of his electoral appeal—he might opt to do nothing or even look for alternatives that involve some level of engagement. Sending food and medicine as humanitarian assistance channeled through the International Committee of the Red Cross and the Catholic Church’s Caritas would reduce migration pressure without directly benefiting the government. Authorizing measures to facilitate the development of Cuba’s private sector, which Trump claimed to support during his first term, would do the same.
Cuban Foreign Minister Bruno Rodríguez predicted that normalizing U.S.-Cuban relations would be a “complex and certainly long process,” when he spoke at the ceremony reopening the Cuban Embassy in Washington in 2015. “The challenge is huge because there have never been normal relations between the United States of America and Cuba,” he said. Clearly, he was right. Historic and successful as it was, the Obama-Castro détente proved to be easily reversed by political forces in Washington more comfortable with the hostility and conflict of the past than with the future promise of constructive engagement and coexistence.
But the key lesson from the fleeting rapprochement that began 10 years ago on Dec. 17, 2014, is that engagement benefits both countries and that bold and determined leaders can make it happen. The enthusiasm with which Cubans, Americans, and people around the world embraced the prospect of peace between the United States and Cuba underscored just how long overdue reconciliation was. Both Obama and Raúl Castro spoke of rebuilding bridges between their countries, and both acknowledged it would be hard to put decades of animosity to rest. It has proven harder than anyone expected in the halcyon days following Dec. 17, but the ties that bind Cuba and the United States—ties of family, commerce, culture, and the shared interests that come from living next door to one another—will eventually overcome the resistance of even the most recalcitrant politicians. As Henry Kissinger recognized half a century ago, “perpetual antagonism” between the United States and Cuba need not be normal.