The CIA Goes to Cuba

A US Air Force C-40B carrying a CIA delegation arrived in Havana on May 14 for an overt meeting with Cuba’s intelligence leadership. The delegation was headed by CIA Director John Ratcliffe and included discussions with Raúl Guillermo Rodriguez Castro, who has conducted back-channel talks with the US State Department since February. The CIA posted photos publicly and both sides issued statements. Cuba said the talks aimed to support political dialogue amid complex bilateral relations. The CIA said Ratcliffe delivered President Donald Trump’s message that the United States would seriously engage on economic and security issues only if Cuba made fundamental changes. The mission is framed as a shift from covert pressure toward an explicit ultimatum tied to past US actions and threats.

"On May 14, an Air Force Boeing C-40B Clipper jet with "United States of America" emblazoned on its fuselage touched down at Jos Mart International Airport in Havana. It carried a high-level delegation of CIA officials, headed by CIA Director John Ratcliffe. Ratcliffe and his team soon sat down with the leadership of Cuba's intelligence community, as well as Ral Guillermo Rodriguez Castro-the grandson of Ral Castro, who has been conducting back-channel talks with Secretary of State Marco Rubio's office since February."

"This was hardly a clandestine meeting. The CIA quickly posted photos of the session on X. Both the Cubans and the CIA have issued statements. The discussions, according to the Cuban government, took place "in the context of complex bilateral relations...to contribute to a political dialogue between both nations." CIA officials stated that Ratcliffe's mission was "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 has a long record of covert regime-change efforts in Cuba: the Bay of Pigs, Operation Mongoose, the ZR/RIFLE assassination plots among them. But this overt CIA mission may well become a capstone to that infamous Cold War history. Ratcliffe's trip marks a turning point in the protracted, punitive US efforts to force the Cuban leadership to capitulate to Washington's demands for economic and political regime change."

"Indeed, the official message Ratcliffe carried to Havana was a "do or die" ultimatum. He reportedly reminded the Cubans of what had happened in Venezuela-US Special Forces quickly killed 32 members of Cuba's security team and injured dozens more-when President Maduro did not take Trump's threats seriously"

Read at The Nation