News and Analysis

Communist Cuba Is Back In Trump’s Crosshairs

The administration has repeatedly framed Cuba as a growing national security concern because of its relationships with Russia, China, and Iran.

Drew Berkemeyer
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4 min

The Trump administration has significantly expanded its intelligence presence in Cuba in recent months, according to people familiar with the plans, as Washington intensifies pressure on Havana’s communist regime and prepares for a wider range of potential operations.  

Two people familiar with the administration’s efforts told Politico that the United States has increased intelligence assets on the island. One described the move as a significant expansion of the CIA’s presence, while another said the intelligence buildup could serve as a critical step for future operations against the Cuban government.

The sources cautioned that military action remains far from certain. Expanded intelligence collection can support a wide range of operations, including diplomatic pressure, counterintelligence, recruiting sources inside foreign governments, and preparation for possible military contingencies.

The increased intelligence activity comes as the administration has made Cuba a central target of its broader effort to confront hostile governments in the Western Hemisphere, arguing that the communist regime poses a national security threat just 90 miles from American shores.

Secretary of State Marco Rubio, whose family fled Cuba after Fidel Castro’s revolution, has made confronting the Cuban regime one of the defining priorities of his foreign policy agenda. In July, the State Department released a 99-page report accusing Havana of decades of espionage, ideological influence operations, and support for revolutionary movements around the world.

“For more than six decades, the Cuban regime has been the leading sponsor of radical leftism and Third Worldism in the United States,” Rubio wrote following the report’s release.

The report argued that Cuba’s greatest strategic success has not been military power but its ability to export revolutionary ideology, conduct espionage, and cultivate influence networks inside the United States and abroad.

The administration has repeatedly framed Cuba as a growing national security concern because of its relationships with Russia, China, and Iran.

During a House budget hearing in May, Secretary of War Pete Hegseth told lawmakers that he considers the Cuban regime a threat to the United States after Rep. Mario Díaz-Balart (R-FL) questioned him about Havana’s relationships with America’s foreign adversaries.

“I do,” Hegseth said when asked whether he believes Cuba poses a national security threat.

One administration official described Cuba as a major priority for Rubio, who believes Washington has run out of patience with a regime that has resisted years of diplomatic engagement and economic pressure.

The Trump administration has already increased pressure on Havana through renewed sanctions and an energy blockade that has contributed to widespread blackouts across the island. 

Officials have also intensified public messaging against the regime. The State Department’s recent report accused Havana of serving as a hub for Russian, Chinese, and Iranian intelligence activity while maintaining its own espionage networks against the United States.

Although U.S. intelligence agencies have long operated in Cuba, as they do throughout the world, rebuilding capabilities on the island would provide the United States with greater visibility and leverage in the Cuban government’s military, intelligence services, and relationships with foreign powers.

Whether that pressure results in negotiations, internal political change, or a broader confrontation remains unclear. But the expansion of U.S. intelligence activity suggests Washington is preparing for a wider range of possibilities than traditional diplomacy alone.

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