When U.S. President Barack Obama announced a deal to normalize relations with Cuba in 2014, Republican presidential hopefuls denounced it as appeasement—but not Donald Trump. “I think it’s fine, but we should have made a better deal,” he said, “The concept of opening with Cuba is fine.” Now, he aims to prove that he alone can make a better deal. By deepening Cuba’s economic deprivation, Trump hopes to inflict enough pain on the Cuban people that the government will be forced to the bargaining table for a “deal” tantamount to surrender.
In the aftermath of the capture of Venezuelan President Nicolás Maduro and his wife Cilia, observers wondered whether Cuba would be next. At first, Trump seemed reluctant. Asked by reporters if he would strike at Cuba, he replied, “It looks like it’s going down. I don’t think we need any action.” A few days later, he seemed to reject the idea of increasing pressure on Havana. “I don’t think you can have much more pressure other than going in and blasting the hell out of the place.” He predicted that Cuba would “go down … of its own volition.”
But giddy with success at his control of Venezuelan oil, and egged on by U.S. Secretary of State Marco Rubio, who made his political career pushing hard-line policies on Havana, Trump announced on social media on Jan. 11, “THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA – ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE.”
Word soon leaked that the Trump administration was planning something far more aggressive than just halting Venezuelan oil shipments. The U.S. Chargé in Havana, Mike Hammer, told his staff to pack their bags, anticipating a break in relations. “The Cubans have complained for years about ‘the blockade,’” Hammer said. “But now there is going to be a real blockade. Nothing is getting in. No more oil is coming.” Politico quoted a person familiar with the American plan as saying: “Energy is the chokehold to kill the regime.”
Rather than a naval blockade, Trump turned to his favorite , all-purpose economic bludgeon—tariffs. On Jan. 29, he declared a national emergency, claiming Cuba posed “an unusual and extraordinary threat” to the United States, which allowed him to impose tariffs on any nation shipping oil to Cuba. The tariff threat is aimed at deterring Havana’s oil-producing friends—including Mexico, Brazil, Angola, and Algeria—from making up the fuel deficit caused by the loss of Venezuelan oil.
Since issuing the executive order, Trump has repeatedly called on Cuban leaders to make a deal, and administration officials have anonymously revealed that Washington is seeking regime change by this year’s end. Multiple sources reported that the administration is searching for someone high enough in the Cuban government to play the role of Delcy Rodríguez—someone able to seize power and willing to surrender to U.S. hegemony in exchange for sanctions relief.
But finding that person may prove harder than Trump and Rubio think. Cuba’s regime no longer depends on the charismatic authority of Fidel or Raúl Castro. It has evolved into a collective leadership drawn from the government bureaucracy, the Communist Party apparatus, and the armed forces—a leadership that has shown considerable cohesion in the face of U.S. threats. A Venezuelan-style decapitation strategy will not work in Cuba.
A Cuban version of Rodríguez would need the support of the armed forces and loyalty from the government and Communist Party to run the country. Even identifying such a person will be nearly impossible. The internal workings of the Cuban regime, especially the armed forces, are largely opaque to U.S. policymakers, according to former U.S. ambassador Jeffrey DeLaurentis, who served three tours of duty in Havana.
A more productive strategy would be to open a dialogue with the current Cuban government, which has always been willing to negotiate with the United States, though rarely willing to make major concessions. Under the current circumstances in which Cuba has few options, however, the parameters of a possible deal may be broader than in the past.
Cuba’s economic crisis, which predates Trump, was already severe and getting worse before Venezuelan oil was cut off. A complete energy blockade, if Washington is able to impose it, would push the Cuban economy to a breaking point, reducing the Cuban people to “subsistence” according to economist Ricardo Torres. That gives Cuban negotiators a strong incentive to make a deal.
Trump’s priorities in Venezuela are to secure U.S. access to commercial opportunities and push out U.S. rivals Russia and China, while maintaining stability on the ground to limit migration and avoid another quagmire like Iraq. If those same priorities apply in Cuba, a deal may just be possible.
Cubans would welcome U.S. commercial engagement. The main obstacle is the U.S. embargo. But current conditions on the island make it an unattractive place to do business. Havana could agree to take steps to improve the business climate for U.S. trade and investment in exchange for sanctions relief. Cuba has significant deposits of nickel and cobalt, which would be attractive to the Trump administration, given its priority to secure access to strategic minerals.
Cuba also has a large tourism sector that is currently languishing for lack of visitors and resources. Trump clearly recognizes this opportunity. Before he was first elected in 2016, he sent representatives to Cuba on several occasions to explore business opportunities in hotels and golf courses.
Cuba’s close relations with both Russia and China have been a long-standing U.S. security concern. Those relations are primarily commercial, but military and intelligence ties have been gradually expanding. Cuba insists that it does not host any foreign bases, which could be the starting point for a dialogue about limiting Cuban military cooperation with extra-hemispheric powers if the threat from the United States recedes. On the commercial front, neither China nor Russia can compete with the United States as a source of trade and investment.
No doubt other long-standing issues would be on the table, as well, including claims for the expropriated properties of both U.S. investors and Cuban Americans. Trump recently said that he wanted to ensure that Cuban Americans were “taken care of” because they had been such loyal supporters. Although Cuba currently has no money to pay compensation, there are a variety of models and historical experiences to turn to if both sides have the political will to settle the issue.
Washington has long demanded the return of aging political fugitives from the 1970s who were given political asylum in Cuba. Although their return is unlikely, formal protocols for the handover of common criminals, which Cuba has been doing on an ad hoc basis, are well within the realm of possibility. The release of political prisoners is also a perennial issue on the U.S. negotiating agenda, and when bilateral relations are improving, Cuba has been responsive.
The issue of democracy, however, would be a sticking point. Since 1961, when Che Guevara first told Richard Goodwin, U.S. President’s John F. Kennedy’s assistant counsel, that Cuba would never discuss “giving up the type of society” for which they fought the revolution, Cuba has been unwilling to make concessions about its political or economic systems.However, democracy is not high on Trump’s agenda, as shown by his sidelining of opposition leader María Corina Machado in Venezuela. Promoting democracy smacks of nation-building and risks destabilizing established institutions, leading to chaos—according to the administration’s thinking. Just as the trauma of Vietnam produced the “Vietnam syndrome,” Trump and his MAGA base have an “Iraq syndrome”—an aversion to “endless wars” fought to spread democracy at the point of a bayonet.
In short, a deal is possible. According to Trump, Washington has already opened a dialogue with someone on the Cuban side. “We’re talking to the people from Cuba, the highest people in Cuba,” he told reporters at Mar-a-Lago on Feb. 1. “We’re pretty close,” he said from the Oval Office the next day. “We are dealing with the Cuban leaders right now.”
Trump’s comments have sparked a wave of speculation about what may be going on behind the scenes. Reports have focused on Mexico, where President Claudia Sheinbaum has repeatedly offered to act as interlocutor. Mexico has a long history of facilitating secret talks between Washington and Havana, from the Carter to Obama administrations. In 2014, Mexico hosted at least one of the secret meetings between top White House aides and a Cuban team led by Gen. Alejandro Castro Espín, the son of then-President Raúl Castro, which led to Obama’s opening to Cuba.
Reports are circulating that Castro Espín’s recent trip to Mexico included several days of back-channel talks with U.S. officials to explore an accord addressing U.S. security and economic interests while leaving Cuba’s government structure intact.
Politico noted that “several Cuban dissident outlets reported that Castro Espín traveled to Mexico City to meet with U.S. officials and propose an off-ramp for the regime.” In a recent interview with Reuters in Havana, Cuban Deputy Foreign Minister Carlos Fernández de Cossío acknowledged, “We have had exchange of messages, we have embassies, we have had communications, but we cannot say we have had a table of dialogue.”
Failure to reach a deal will be disastrous—but not only for Cuba. Cutting off Cuba’s oil is a risky strategy. The aim is to make the economy scream—to inflict so much pain that either the regime cries uncle or some faction within it seizes power and accedes to U.S. demands, just as the remnants of the Chavista regime have done in Venezuela. “We don’t have an interest in a destabilized Cuba,” Rubio told oil executives at the White House. But if the oil blockade triggers economic and social collapse, then the consequences for the United States will be grave.
Washington faced this risk once before, during what Cuba called the “Special Period” after the collapse of the Soviet Union—which had been Cuba’s main ally and benefactor. In August 1993, the CIA drafted a secret National Intelligence Estimate (NIE) that could have been written today. “The impact on the population already has been devastating,” the NIE reported, citing the scarcity of basic goods and the electricity blackouts of 10 to 16 hours a day. “Food shortages and distribution problems have caused malnutrition and disease, and the difficulties of subsisting will intensify.”
U.S. officials recognized that a “failed state” in Cuba constituted a national security threat. The advent of “serious instability in Cuba [would] have an immediate impact on the United States,” the intelligence community concluded, citing massive uncontrolled migration, agitation in the Miami exile community, and increased “pressures for US or international military intervention”—all likely consequences today, as well.
A defiant Fidel Castro once said that Cuba would never negotiate with “a dagger at our throat,” but the dagger, newly sharpened, is pressing more deeply into Cuba’s flesh now than ever before. In public, Cuba’s leaders still declaim, “¡Patria o muerte!” (which translates to “Homeland or death!”). But given the suffering that the Cuban people are enduring and what may lie ahead, it makes sense to explore whether they can reach a deal with the Trump administration that preserves Cuban sovereignty even at the price of compromise on other policies.
For the first half of the 20th century, the United States enjoyed the kind of dominion over Cuba that the Trump administration is trying to restore—the power to dictate who governed the island and near total control over its economy. “The American ambassador was the second-most important man in Cuba,” said Earl E.T. Smith, a former U.S. ambassador. “Sometimes even more important than the president.” The nationalist resentment that Cuba’s vassalage evoked exploded in the 1959 revolution while Smith was in Havana. The result has been more than half a century of hostility that has served the interests of neither country. Washington would be wise to avoid repeating that sad history.
