NEW: Trump Sends CIA Director To Cuba Amid Rising Tensions

CIA Director John Ratcliffe held high-level talks in Cuba on Thursday, meeting with senior officials and Raúl Castro’s grandson as the Trump administration pressed Havana on security and economic issues amid strained relations, U.S. and Cuban officials said.

Ratcliffe met with Raúl Guillermo Rodríguez Castro, Interior Minister Lázaro Álvarez Casas and the head of Cuba’s intelligence services, according to officials. A CIA official confirmed the meetings to the AP.

Ratcliffe traveled to the island “to personally deliver President Donald Trump’s message that the United States is prepared to seriously engage on economic and security issues, but only if Cuba makes fundamental changes,” the CIA official said.

Cuba’s government, in an official statement, said the meeting “took place … against a backdrop of complex bilateral relations.”

U.S. officials, according to the CIA account, warned that Cuba cannot remain a “safe haven for adversaries in the Western Hemisphere.” Cuban officials countered that the island poses no threat to U.S. security and objected to Cuba’s continued presence on the U.S. list of state sponsors of terrorism.

🚨 JUST IN: US government planes were spotted on the tarmac of Cuba’s primary airport in Havana

This particular Boeing C-40 was confirmed as being used by CIA Director John Ratcliffe for a visit to Cuba.

The CIA was clearly making a statement using this particular plane.

The… pic.twitter.com/yiXWVWWWdG

— Nick Sortor (@nicksortor) May 14, 2026

Rodríguez Castro has previously met quietly with U.S. officials. He secretly met with Secretary of State Marco Rubio on the sidelines of a Caribbean Community summit in St. Kitts in February, the report said. While Rodríguez Castro has not held a formal government post, he served as his grandfather’s bodyguard and later led Cuba’s equivalent of the Secret Service.

U.S. and Cuban officials have also held talks on the island earlier this year. Those ongoing contacts mark the first U.S. government flights to land in Cuba, outside the U.S. Naval Base at Guantanamo Bay, since 2016.

RELATED: NEW: U.S. Plans To Indict Cuban Dictator Raul Castro

The latest meeting comes as tensions remain high over the U.S. energy blockade of Cuba and the country’s worsening power crisis. Cuba has suffered grid failures, and energy to parts of the eastern provinces has been cut, while fuel restrictions have deepened economic strain, including reduced work hours and food spoilage as refrigerators shut down.

Earlier this week, the State Department reiterated that the United States would provide Cuba with $100 million in humanitarian assistance and support for satellite internet “if the Cuban regime will permit it.”

RELATED: NEW: Trump Hints At ‘Immediate’ U.S. Action In Cuba

In late January,  Donald Trump threatened tariffs on any country that sells or supplies oil to Cuba. Trump has also raised the possibility of intervention. Cuban President Miguel Díaz-Canel has said the country is prepared to fight if that happens, though sources told the AP earlier this month that military action is not imminent.

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