Will the Trump administration settle for a deal with Cuba that opens up key sectors of the economy to U.S. investors, including Cuban Americans? Or will it demand political concessions amounting to regime change? An economic deal is within the realm of possibility, since the Cuban government has been slowly—too slowly—moving in that direction already. But allowing the United States to dictate the shape of Cuba’s political future is almost certainly a bridge too far for Havana.
A purely economic deal would be a surprise, given the hard-line position of U.S. Secretary of State Marco Rubio, who has said for years that the government in Havana must go. But recent statements by him and other Trump officials as well as reports about negotiations underway suggest that the administration might settle for something less than regime change—just as it has in Venezuela. The New York Times reported on Tuesday that Washington is pressing for the replacement of Cuban President Miguel Díaz-Canel with someone more open to economic reform, an essentially symbolic gesture that would leave the rest of the regime intact.
Díaz-Canel confirmed on March 13 that Cuba and the United States have been engaged in conversations “aimed at seeking solutions through dialogue to the bilateral differences that exist between the two nations” and “to identify areas of cooperation.” He did not specify any points of agreement yet or what specific issues are on the table, noting that “we are in the initial phases of this process.”
The day before, Cuba announced the impending release of 51 prisoners, facilitated by the Vatican—a gesture that has frequently accompanied talks between Havana and Washington. In his press conference, Díaz-Canel also held out an olive branch to the Cuban diaspora, promising to offer Cubans residents abroad “opportunities to participate in in the economic and social life of the country.” On Monday, the minister for foreign trade and investment announced that Cubans abroad would be able to own or invest in private enterprises on the island, use the financial system, and even partner with state enterprises—access that Cuban American entrepreneurs have long sought.
U.S. President Donald Trump has been talking about the negotiations with Cuba in press gaggles for more than a month, insisting that Rubio has been dealing with Cuban officials at a “very high level” and that a deal is almost done.
“They want to make a deal so badly, you have no idea,” he said on March 5. The terms of the deal being discussed reportedly focus on economics more than politics, with potential agreements on ports, energy, and tourism in exchange for some relief from U.S. sanctions. Washington also aims to strengthen Cuba’s private sector as a counterweight to the state sector of the economy.
Rubio has repeatedly implied that the administration places a high priority on economic change and is willing to accept a gradualist approach. “Cuba needs to change, and it doesn’t have to change all at once. It doesn’t have to change from one day to the next,” he said during the Caribbean Community (Caricom) meeting on regional cooperation in February. “Everyone is mature and realistic here.”
Rubio’s team has been talking with Raúl Castro’s grandson, Col. Raúl Guillermo Rodríguez Castro, the head of his grandfather’s personal security. The 41-year old colonel enjoys a notoriously jet-setting lifestyle, causing U.S. officials to view him as “representing younger, business-minded Cubans for whom revolutionary communism has failed — and who see value in rapprochement with the U.S.” according to Axios.
Rodríguez Castro is also the son of the late Gen. Luis Alberto Rodríguez López-Calleja who, along with Raúl Castro, built the military’s business conglomerate GAESA into an economic powerhouse. Rodríguez Castro is said to be his grandfather’s liaison with GAESA, which would play a critical role in any deal with Washington to open up the Cuban economy.
On the sidelines of the Caricom conference, a top advisor to the secretary of state reportedly met with Rodriquez Castro at a St. Kitts hotel. Among the issues they discussed, sources told the Miami Herald, was Washington’s willingness to gradually lift economic sanctions in exchange for gradual reforms in Cuba, “on a month-to-month basis.”
This quid pro quo approach is not new. Former U.S. President Bill Clinton was ready to launch a policy of “calibrated response” with a speech drafted in 1994 proposing that, “as the Cuban government implements concrete and verifiable measures” to improve human rights and reduce regulations on private businesses, “we will unilaterally reduce sanctions affecting trade and seek to improve the full range of relations with Cuba and its people.”
The speech was never given. Before the “calibrated response” policy got off the ground, it was overtaken by events—the mass exodus of Cubans known as the balsero (rafters) crisis. Rubio’s “month-by-month” approach risks a similar fate. Cuba’s economic situation is so desperate that a new mass migration crisis could erupt if significant sanctions relief does not come soon.
Rubio is a Cuban American who built his political career as a vocal opponent of any U.S. opening toward Cuba. But his willingness to pursue a gradualist policy that prioritizes economic reform and only gets around to political change “eventually” echoes the president’s priorities in Venezuela, where cementing U.S. access to oil and maintaining stability have trumped a transition to democracy. A powerful opposition movement in Venezuela won the election in 2024, but President Nicolás Maduro falsified the results to stay in power.
Trump, at his recent Shield of the Americas summit for like-minded conservative leaders, praised Venezuela’s interim president, Delcy Rodríguez, who was Maduro’s vice president before U.S. forces abducted him in January. “We’ve been working closely with the new president of Venezuela, Delcy Rodríguez, who’s doing a great job working with us,” Trump said. Asked by journalists why he was leaving the Venezuelan regime built by Hugo Chávez largely intact, Trump reminded them of the chaos that ensued after regime change in Iraq, “where everybody was fired.”
The prospect that Trump, who won 70 percent of Florida’s Cuban American vote in 2024, and their favorite son Rubio might cut an economic deal that leaves the regime built by Fidel Castro in place is anathema to Cuban American hard-liners. Responding to reports that a deal might be close, Rep. Carlos Giménez wrote on X, “It has to lead to a transition away from these dictators, away from the authoritarian regimes.” Giménez, along with Rep. Mario Diaz-Balart, has demanded that Trump tighten the economic screws even more by cutting off commercial air travel to Cuba and prohibiting Cuban Americans from sending remittances to their families—demands that the administration has so far ignored.
Trump frequently says that he will take care of Cuban Americans, who were among his most loyal supporters in the 2016, 2020, and 2024 elections. But Trump is not running again, so Cuban Americans in Miami can no longer call the shots on Cuba policy. That became clear on Feb. 25, when 10 heavily armed exiles tried to infiltrate the island. They were intercepted by the Cuban coast guard and in the firefight that followed, five were killed. The rest were wounded, taken into custody, and charged with terrorism.
Miami hard-liners compared the incident to the 1996 shootdown by Cuban MiGs of two aircraft from an organization called Brothers to the Rescue, in which four pilots were killed. But rather then seize on the incident as a pretext for retaliation, the Trump administration reacted calmly, acknowledging that Cuba had informed the United States of the event when it happened through regular channels used for cooperation on maritime safety and security. Rubio promised a full investigation, and Díaz Canel has announced that Cuba may receive an FBI delegation as part of that investigation.
This muted response signals that Trump’s self-interested transactional approach to foreign policy, not ideological anti-communism, is driving policy toward Cuba. But whether Washington and Havana can reach an agreement to avert a U.S. military assault depends on whether there is enough common ground between the minimum conditions that Trump is willing to accept in a deal and the maximum concessions that Cuban leaders are willing to make.
Demands from Washington for political change, even symbolic ones, may be too bitter a pill, and too blatant an affront to Cuba’s sovereignty, for any Cuban leader to swallow. Monday’s front page headline in the Communist Party newspaper Granma read, “Baraguá Protest: Eternal Symbol of the Revolutionary Intransigence that Guides Cuba.” The article celebrated the refusal of independence hero Antonio Maceo to accept a treaty that ended Cuba’s first war of independence but left Spanish colonialism intact.
If Cubans refuse to bend the knee, Trump could send the U.S. military to knock them to their knees. “It may be a friendly takeover, it may not be a friendly takeover,” Trump warned in early March. “They’re going to make either a deal, or we’ll do it, just as easy, anyway.” In an interview with CNN this month, the president promised that he and Rubio would turn to Cuba as soon as they finished with Iran.
With Venezuela coerced into subservience and Iran under withering attack by the United States and Israel, Trump has hopes of winning the regime-change trifecta with a “friendly takeover” of Cuba.
“The president is feeling like, ‘I’m on a roll,’” an administration official told the Atlantic. Overthrowing the government born out of revolution in 1959 has been the dream of successive U.S. presidents for more than half a century. Trump is convinced that the moment is at hand, and he will be the president who gets the job done. “I do believe I’ll be having the honor of taking Cuba,” he told reporters in the Oval Office on March 16. “Taking Cuba in some form. I mean, whether I free it or take it. I think I could do anything I want with it.”
Trump’s confidence that Cuban leaders will surrender to U.S. demands stems from the sorry state of their economy, made worse by the intensification of U.S. sanctions, especially the blockade of not just Venezuelan oil shipments but all oil shipments.
Trump’s rhetoric, his new National Security Strategy, and his aggressive policies toward Venezuela and Cuba, all imply that Washington regards the Western Hemisphere as a region where other countries are allowed only limited sovereignty—an idea Latin Americans spent most of the past century trying to overcome.
