Updated: May 22, 2026 / 6:04 PM EDT / CBS News
CIA Director John Ratcliffe’s recent visit to Havana marked a significant meeting with senior Cuban officials. Accompanying him was an operator involved in capturing former Venezuelan leader Nicolás Maduro, according to sources. This visit appears to send a deliberate message, as Venezuela and Cuba were allies before Maduro’s arrest. The Cuban government reported that 32 military and police officers were killed during the January operation, which extracted Maduro.
Ratcliffe introduced the paramilitary leader to Cuban officials, emphasizing his role in the operation that resulted in Cuban casualties, several sources disclosed. His presence may have been intended as a direct signal to the Cuban government.
The CIA refused to comment on the matter. The backdrop to Ratcliffe’s visit involves mounting pressure on Cuba, with threats of hefty tariffs on countries exporting oil to the island. This led to significant fuel shortages. Secretary of State Marco Rubio stressed the need for economic and political reforms, and President Trump has considered a potential ‘friendly takeover’ of Cuba.
Rubio pointed out Cuba’s connections to Venezuela post-raid, noting that Venezuela’s “spy agency” is heavily staffed with Cubans, drawing concern for Havana’s government. He stated, “If I lived in Havana and I was in the government, I’d be concerned, at least a little bit.”
A CIA official asserted Ratcliffe’s message to Cuba was clear: the U.S. is ready to engage on economic and security fronts, but only if Cuba implements fundamental changes.
During the meeting, Ratcliffe spoke with Raúl Rodriguez Castro, known as “Raulito,” grandson of former President Raúl Castro. Days later, a U.S. court indicted the 94-year-old Castro for alleged murder and conspiracy relating to the 1996 downing of two planes.
This meeting recalls the prolonged Cold War era struggle, shaping U.S.-Cuba relations for over fifty years. Memories of the Bay of Pigs invasion and Operation Mongoose persist among Cuban officials, impacting current diplomatic interactions.
Rubio commented that Cuba, aside from possessing Russian and Chinese weapons, also hosts foreign intelligence presence within the country. The CIA emphasized that Cuba must no longer be a haven for adversaries in the Western Hemisphere.
Simultaneously, as tensions mount, the U.S. intelligence community investigates Cuba’s potential responses to American military actions. Reports from CBS News indicate Cuba has acquired attack drones. President Miguel Díaz-Canel Bermúdez assured that Cuba poses no threat to the U.S. but cautioned about potential “bloodbath” with military strikes.
Olivia Gazis contributed to this report.
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