The United States has increased its intelligence assets in Cuba in recent months, including deploying additional spies and expanding the Central Intelligence Agency’s presence on the island, according to a report published by POLITICO.
Citing “two people familiar” with the Trump administration’s plans, the move is allegedly part of a broader effort to pressure Cuba’s communist government to reform or collapse and could support options ranging from stepped-up efforts to recruit Cuban officials or citizens to a potential U.S. military operation.
The intelligence expansion follows a rare high-level visit to Havana in mid-May 2026 by CIA Director John Ratcliffe.
During the trip, Ratcliffe reportedly met with Raúl Guillermo Rodríguez Castro, the grandson of former Cuban leader Raúl Castro, Interior Minister Lázaro Álvarez Casas and the head of Cuban intelligence services.
He personally delivered President Donald Trump’s message that the United States is prepared to engage seriously on economic and security issues only if Cuba makes fundamental changes. The discussions also covered intelligence cooperation, economic stability and security concerns, with emphasis that Cuba can no longer serve as a safe haven for U.S. adversaries such as Russia and China in the Western Hemisphere.
Senior officials accompanied Ratcliffe, with a subsequent report revealing that the delegation included a paramilitary operator involved in the earlier U.S. capture of former Venezuelan dictator Nicolás Maduro.
In tandem with the intelligence expansion, Washington significantly intensified aerial surveillance around Cuba starting early this year — flooding the surrounding airspace with P-8 Poseidon maritime patrols, RC-135 Rivet Joint reconnaissance planes and high-altitude MQ-4 drones.
Cuban officials have since criticized the heightened U.S. intelligence and related pressure as “unlawful attempts to destabilize the island.” Nonetheless, Trump administration officials maintain that a stronger intelligence posture is necessary to protect American national security, track foreign adversaries operating in Cuba and maintain leverage as economic conditions deteriorate and diplomatic talks remain stalled.
Hellbound and Down 