President Donald Trump has placed Cuba at the forefront of his foreign policy strategy, consistently stating the Communist-governed nation will be “next” after U.S. military operations in Venezuela and Iran, while clandestine talks between Washington and Havana persist in private.
The intensifying language has prompted analysts to wonder whether the Trump administration is pursuing authentic regime change, a controlled transition, or merely increased opportunities for American corporations on the island located just 90 miles from Florida’s coastline.
During remarks at the Future Investment Initiative summit in Miami on March 27, Trump discussed his administration’s recent military achievements before turning his attention 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.”
These remarks came after the U.S. military’s detention of Venezuelan President Nicolás Maduro on Jan. 3, and the assassination of Iranian Supreme Leader Ali Khamenei in combined U.S.-Israeli operations on Feb. 28. Trump has become progressively emboldened in his declarations, informing journalists on Air Force One, “Cuba’s going to be next.”
Secretary of State Marco Rubio, whose parents emigrated from Cuba, has articulated the administration’s goals more directly. Rubio testified to Congress in January, “We would love to see the regime there change.” In March, he stated that Cuba’s leadership “don’t know how to fix it, so they have to get new people in charge.”
The Trump administration has been choking Cuba’s economy via an oil embargo that specialists claim has driven the island to its most critical condition since the Soviet Union’s demise. The approach escalated after the cessation of oil deliveries from Venezuela following Maduro’s detention, leading to widespread electrical failures throughout Cuba.
The embargo displayed indications of uneven implementation in late March, when a Russian vessel transporting approximately 700,000 barrels of crude oil docked at the port of Matanzas without U.S. interference. The White House indicated the delivery did not constitute a formal modification in sanctions policy and that subsequent choices would be determined case-by-case. Trump, speaking on Air Force One, minimized the occurrence, saying: “Cuba’s finished.”
Notwithstanding the confrontational stance, both governments have verified continuing dialogue. Cuban President Miguel Díaz-Canel acknowledged in March that conversations are underway but remain “still far from an agreement.” Cuba’s deputy foreign minister, Carlos Fernández de Cossío, characterized the discussions as both serious and sensitive, while maintaining that regime change is “absolutely” off the table.
The matter of what “taking Cuba” genuinely signifies has split observers and potentially the administration as well. Paul Hare, who functioned as British ambassador to Cuba from 2001 to 2004, recognized rival groups within Trump’s circle—some prepared to negotiate agreements with current leadership for commercial entry, others demanding total 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 observed that Cuba’s authority structure has persisted for almost seven decades and demonstrates expertise at suppression, rendering it a more difficult objective than Venezuela.
Lawrence Gumbiner, a career diplomat who directed the U.S. Embassy in Havana during Trump’s first term, presented an alternative perspective. He proposed Trump perceives Cuba as untapped ground for American commercial ventures after six decades of economic stagnation, with possibilities covering shipping, transportation, tourism, and construction.
Gumbiner forecasted any resolution would include economic liberalization initially, with fresh Cuban leadership functioning under substantial U.S. coercion. He likened the prospective framework to the position currently held by Venezuelan Vice President Delcy Rodríguez, cautioning the directive would be unmistakable: conform or encounter repercussions.
The Cuban government has resisted Washington’s coercion. Deputy Foreign Minister Fernández de Cossío informed NBC’s “Meet the Press” that Cuba’s military remains “prepared” for any U.S. aggression, observing that the world’s most powerful nation has devoted almost seven decades to attempting to dismantle Cuba’s governmental system and failed.
Cuban President Díaz-Canel took over the presidency from Raúl Castro in April 2018, becoming the first individual since 1976 outside the Castro family to officially govern the country. Nevertheless, numerous observers regard Díaz-Canel a figurehead, with the Castro family retaining substantial influence covertly through the military conglomerate GAESA, which dominates roughly 60 percent of Cuba’s economy.
Hernandez-Roy described removing Díaz-Canel’ as chiefly symbolic, observing “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 discussions persist and Trump’s language escalates, the destiny of the island nation remains uncertain. Rubio informed Fox News in February that the administration would “have more news on that fairly soon,” implying notable advances may be nearing in the intricate confrontation between Washington and Havana
The most tangible indication of advancement occurred on April 3, when Cuba freed more than 2,000 detainees, presenting the action as a humanitarian measure for Easter. Analysts at The Guardian interpreted the release as a probable sign of continuing covert negotiations between the two governments.
