The Trump administration is preparing for a potential near-term collapse of Cuba's government and has conducted military planning exercises to ready response options if the island descends into turmoil, according to U.S. officials.
The strategic approach relies on economic strangulation rather than immediate military intervention. One senior administration official characterized the policy as "accelerationism," a method designed to hasten the regime's deterioration through carefully calibrated pressure. "But we don't want to kill off the regime just yet," the official said. "There's a method to this. It's in stages."
The tightening began with Venezuela. By capturing Nicolas Maduro on January 3 in a U.S. military operation, the administration severed the lifeline that had kept Havana afloat. For years, Venezuelan oil shipments provided both the fuel and export revenue Cuba needed to function. That flow has now stopped entirely, pushing the island into acute economic crisis.
On May 1, Trump signed an executive order imposing secondary sanctions targeting foreign companies doing business with GAESA, Cuba's massive military-controlled conglomerate. The order prompted Canadian mining company Sheritt International and shipping firms CMA CGM and Hapag-Lloyd to suspend operations in Cuba. Financial institutions and hotel companies across Spain, Panama, Mexico and other nations are now expected to exit the market.
"We've never seen this kind of pressure," said Max Meizlish, a former Treasury official who specialized in Cuba sanctions. "It's an entirely new ballgame."
Secretary of State Marco Rubio has emerged as the chief architect of Cuba policy, announcing the GAESA sanctions on May 7 and making them central to messaging aimed at Cuban citizens. The timing has been orchestrated for maximum political impact. On May 20, Rubio released a Cuban Independence Day video highlighting the sanctions. That same day, the Justice Department unsealed a federal murder indictment against Raul Castro for allegedly ordering the 1996 Brothers to the Rescue shootdowns. SOUTHCOM announced the arrival of a Nimitz Carrier Strike Group in the region.
Military planners held a multiagency war game last month focused on potential scenarios if the regime fractures. "Everything is on the table, but no invasion is planned or imminent," one official said. Discussions centered on Cuban drone capabilities and how to respond if unrest breaks out as temperatures rise heading into summer. Officials referenced the July 2022 protests, when Cuban authorities brutally suppressed demonstrations. Conditions have deteriorated significantly since then.
"It's going to be hot. People won't have electricity. Food spoils without refrigeration. People get angry," one source said. "They can take to the streets. And then what happens? I can't see the president doing nothing if there's repression."
Yet a Trump adviser offered a contrasting view. "The president does not want boots on the ground for more than 48 hours," the adviser said. "It's a quagmire in the making. This could get messy."
The administration has identified key constraints that distinguish Cuba policy from the Maduro operation. First, Trump has not identified or authorized engagement with any Cuban officials who could lead an interim government if the regime falls. Second, removing the Castros through seizure would not automatically reorient Cuba toward the U.S., since the family began distributing power away from one-man rule decades ago. Third, the Cuban embargo is codified in federal law and cannot be lifted by executive order alone. Congress retains power, and Miami's three Cuban-American representatives hold hardline positions reflecting South Florida's conservative exile community.
The strategy is not all punishment. The U.S. announced this month that it would provide $100 million in assistance to Cuba, channeled through the Catholic Church and charities rather than the government. "If we wanted to hasten the collapse, we would not have sent any assistance," one official said, describing the overall campaign as designed to show Cubans they could prosper if the regime stepped aside.
Cuba's foreign minister, Bruno Rodriguez Parrilla, accused the U.S. and Rubio specifically of manipulating public opinion to justify military intervention.
Trump is currently focused on peace negotiations with Iran and is not rushing decisions on Cuba, officials say. "Trump wants to exhaust all the levers that he can," one official noted. "But at this point, there aren't as many levers as before."
Author James Rodriguez: "The administration is betting it can orchestrate regime change through economic asphyxiation without committing troops, but the military preparations suggest they're bracing for a messier outcome than a managed collapse."
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