CIA Director Ratcliffe leads delegation to Havana, issues ultimatum 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

Demonstrators set fire in Havana, Cuba, in protest against the lack of energy and blackouts in their neighborhoods hit with widespread power cuts on May 14, 2026. (Yamil Lage / AFP via Getty Images)

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, and 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.

"Submission Diplomacy"

The CIA mission to Havana comes only one day after Cuba's minister of energy, Vicente de la O Levy, publicly conceded that the country has, essentially, run out of gas. "We have absolutely no fuel oil, and absolutely no diesel," Cuban Minister of Energy Vicente de la O Levy announced on state television last week. "We have no reserves."

Current Issue: June 2026 Issue

Denying the Cuban people gas and electricity, along with the basic economic functions they enable, has been the concerted goal of Trump's policy of extreme energy deprivation. Since US Special Forces attacked Caracas on January 3, the administration has methodically used threats and coercion to shut down Cuban access to alternative sources of petroleum—with the intent of starving the Cuban people, generating popular unrest, and forcing the Cuban leadership to capitulate.

"The strategy of previous negotiations with Cuba has been to offer Havana carrots," American University professor William LeoGrande said in an interview. "Trump's strategy is to beat the Cubans with a stick until they cry uncle."

As the oil blockade takes a devastating toll on the Cuban people, the Trump administration has turned up the heat of economic warfare on Cuba, targeting foreign investment on the island.

• On May 1, Trump signed a new executive order broadening restrictions on commercial interactions with Cuban entities and applying "secondary sanctions" to foreign businesses that engage with "blocked" Cuban agencies and officials.
• On May 7, Secretary of State Marco Rubio designated the Cuban military corporation GAESA, which administers much of the Cuban economy, as a blocked entity along with the Cuban mining company MOA Nickel SA.

MOA was established as part of a joint venture with the Canadian mining giant Sherritt International, one of the largest foreign investors on the island, which for decades has managed Cuba's nickel and cobalt mining operations. The new secondary sanctions immediately forced Sherritt to announce that it would close its mining operations on the island—and request the Cuban...