President Donald Trump has thrust Cuba into the center of his foreign policy agenda, repeatedly declaring the Communist-ruled island will be “next” following U.S. military interventions in Venezuela and Iran, even as secret negotiations between Washington and Havana continue behind closed doors.
The escalating rhetoric has left experts questioning whether the Trump administration seeks genuine regime change, a managed transition, or simply greater access for American businesses to the island nation just 90 miles from Florida’s shores.
Speaking at the Future Investment Initiative summit in Miami on March 27, Trump addressed his administration’s recent military successes before pivoting to Cuba. “I built this great military. I said you’ll never have to use it but sometimes you have to use it. And Cuba’s next by the way. But pretend I didn’t say that,” the president told the audience before repeating: “Cuba’s next.”
The comments followed the U.S. military’s capture of Venezuelan President Nicolás Maduro on January 3 and the killing of Iranian Supreme Leader Ali Khamenei in joint U.S.-Israeli strikes on February 28. Trump has grown increasingly bold in his statements, telling reporters aboard Air Force One, “Cuba’s going to be next.”
Secretary of State Marco Rubio, the son of Cuban immigrants, has been more explicit about the administration’s objectives. Rubio testified to Congress in January, “We would love to see the regime there change.” In March, he added that Cuba’s leaders “don’t know how to fix it, so they have to get new people in charge.”
The Trump administration has been strangling Cuba’s economy through an oil blockade that experts say has pushed the island to its most desperate state since the Soviet Union’s collapse. The strategy intensified following the loss of oil shipments from Venezuela after Maduro’s removal, contributing to nationwide power blackouts across Cuba.
Despite the aggressive posture, both governments have confirmed ongoing talks. Cuban President Miguel Díaz-Canel acknowledged in March that discussions are occurring but remain “still far from an agreement.” Cuba’s deputy foreign minister, Carlos Fernández de Cossío, described the negotiations as both serious and sensitive, while insisting that regime change is “absolutely” off the table.
The question of what “taking Cuba” actually means has divided analysts and potentially the administration itself. Paul Hare, who served as British ambassador to Cuba from 2001 to 2004, identified competing factions within Trump’s team—some willing to cut deals with existing leadership for business access, others insisting on complete regime change.
Christopher Hernandez-Roy, senior fellow and deputy director of the Americas Program at the Center for Strategic and International Studies, said “regime management” represents the only realistic option. He noted that Cuba’s power structure has endured for almost seven decades and excels at repression, making it a harder target than Venezuela.
Lawrence Gumbiner, a career diplomat who led the U.S. Embassy in Havana during Trump’s first term, offered a different interpretation. He suggested Trump views Cuba as virgin territory for American business interests after six decades of economic dormancy, with opportunities spanning shipping, transportation, tourism, and construction.
Gumbiner predicted any settlement would involve economic openings first, with new Cuban leadership operating under heavy U.S. pressure. He compared the potential arrangement to the role now played by Venezuelan Vice President Delcy Rodríguez, warning the message would be clear: comply or face consequences.
The Cuban government has pushed back against Washington’s pressure. Deputy Foreign Minister Fernández de Cossío told NBC’s “Meet the Press” that Cuba’s military stands “prepared” for any U.S. aggression, noting that the world’s most powerful nation has dedicated almost seven decades trying to destroy Cuba’s governmental system and failed.
Cuban President Díaz-Canel assumed the presidency from Raúl Castro in April 2018, becoming the first person since 1976 not from the Castro family to formally lead the country. However, many analysts consider Díaz-Canel a figurehead, with the Castro family maintaining considerable influence behind the scenes through the military conglomerate GAESA, which controls roughly 60 percent of Cuba’s economy.
Hernandez-Roy characterized removing Díaz-Canel’ as primarily symbolic, noting “he’s not the person that actually wields the power in the country, but it would be seen as a symbolic win by the United States.”
As negotiations continue and Trump’s rhetoric intensifies, the fate of the island nation hangs in the balance. Rubio told Fox News in February that the administration would “have more news on that fairly soon,” suggesting significant developments may be approaching in the complex standoff between Washington and Havana