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‘This Could Get Messy’: Trump Officials Spill on Plans fo...
David Gilmour · 2026-05-28 · via Mediaite

Donald Trump

(AP Photo/Alex Brandon)

Senior Trump administration officials have reportedly gamed out plans for military action against Cuba as the White House ramps up pressure on Havana and braces for the possibility of political unrest on the island.

The discussions, reported exclusively by Axios on Thursday, which included a recent “tabletop” exercise led by U.S. Southern Command, come as the administration intensifies sanctions aimed at destabilizing Cuba’s communist government using strict sanctions.

“Everything is on the table, but no invasion is planned or imminent,” one senior administration official told the outlet. “When POTUS says go, we’re ready for anything.”

Officials reportedly believe worsening economic conditions, including blackouts and food shortages — coupled with rising summer temperatures, might trigger unrest similar to the anti-government protests that erupted across the island in 2021.

“It’s going to be hot,” a source told Axios. “People won’t have electricity. Food spoils without refrigeration. People get angry. They can take to the streets. And then what happens? I can’t see the president doing nothing if there’s repression.”

The administration officials told the site that President Donald Trump is not in a “rush” and wants “to exhaust all the levers that he can,” which is why the apparent strategy involves an escalating pressure campaign designed to weaken Cuba.

“The best way to describe it is ‘accelerationism.’ But we don’t want to kill off the regime just yet. There’s a method to this. It’s in stages,” one official said.

“We have time. The regime doesn’t,” another remarked.

Secretary of State Marco Rubio has emerged as a central figure in the effort, pushing sanctions targeting GAESA, Cuba’s military-linked business conglomerate. Trump also signed an executive order imposing secondary sanctions on foreign companies doing business with the group, prompting several international firms to suspend operations tied to Cuba.

Despite the increasingly hawkish posture, some advisers warned against prolonged military involvement.

“The president does not want boots on the ground for more than 48 hours,” one Trump adviser told Axios. “It’s a quagmire in the making. This could get messy.”

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