The CIA Goes to Cuba

After decades of covert operations, the CIA director has given the Cubans an overt ultimatum for change on the island.

By Peter Kornbluh, The Nation

On May 14, an Air Force Boeing C-40B Clipper jet with “United States of America” emblazoned on its fuselage touched down at José Martí 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 Raúl Guillermo Rodriguez Castro—the grandson of Raúl 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. As the CIA director warned the Cubans, the window for diplomatic dialogue will soon close unless they act on US demands for change; and President Trump plans to “enforce his red lines” if negotiations do not produce the results he desires.