Trump hints at progress in talks with Cuba, floats 'friendly takeover' of the island

Nora Gámez Torres, Miami Herald on Feb 27, 2026

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President Donald Trump hinted Friday that talks with Cuban leaders are progressing and suggested the island’s profound economic collapse could open the door for the United States to regain significant influence over decisions on the Caribbean island just 90 miles off the Florida Keys.

“The Cuban government is talking with us,” Trump said. “They’re in a big deal of trouble, as you know, they have no money. They have no anything right now, but they’re talking with us, and maybe we’ll have a friendly takeover of Cuba.”

“We could very well end up having a friendly takeover of Cuba,” he repeated.

Whether Trump’s “friendly takeover” amounts to a negotiating posture or an offhand remark was unclear. The remarks came as the Miami Herald reported fresh details of those behind-the-scenes contacts.

Secret talks in Saint Kitts

On Wednesday, U.S. officials close to Secretary of State Marco Rubio met with Raúl Castro’s grandson on the sidelines of the annual meeting of Caribbean leaders in the capital of Saint Kitts and Nevis, as efforts to negotiate economic and political changes in Cuba continued.

Multiple sources with knowledge of the meeting said Raúl Guillermo Rodriguez Castro met with one of Rubio’s close advisers in a hotel near where the 50th meeting of the Caribbean Community was taking place. Herald sources said they discussed the possibility of gradually easing U.S. sanctions in exchange for Cuban leaders enacting changes on the island.

A Caribbean diplomat privy to discussions between Rubio and Caribbean leaders said he suggested that talks with Cuba were “well advanced,” though another source said a deal had not been reached yet.

The diplomatic maneuvering is unfolding against a backdrop of renewed tensions. Also on Wednesday, the Cuban government said its coast guard exchanged gunfire with a Florida-registered speedboat of armed Cuban exiles, killing four people and wounding six. Cuban officials said the boat neared the island and opened fire first, and that they later found guns, explosives, and combat gear on board. One of the four people killed was an American citizen, the U.S. State Department confirmed.

Cuba’s economy is in free fall. The Trump administration stopped oil shipments from Venezuela and Mexico to Cuba, to bring Cuban leaders to the negotiating table. But the standoff is also aggravating a humanitarian crisis already unfolding on the island. Trump himself had recently described Cuba as a “failing nation” and the U.S. government has offered humanitarian assistance to the island.

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