CIA Secretly Forms Cuba Task Force With Plans to Destabilize Havana

The task force's stated mandate is to create fractures within Cuba's political elite.

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The CIA has secretly established a Cuba task force to pressure Havana into political and leadership changes demanded by President Trump, according to a report by The New York Times.

Key Developments

The CIA has quietly set up a dedicated Cuba task force, staffing it with case officers, intelligence analysts, cyber operations officers, and covert influence specialists.

The move coincides with the Trump administration designating Cuba a National Intelligence Priorities Framework Priority 1 target, placing it alongside China, Iran, and Russia.

In response, the NSA, the National Geospatial-Intelligence Agency, and other intelligence bodies have begun redirecting satellites and collection assets toward the island.

CIA Director John Ratcliffe traveled to Havana in May to meet with Raúl Castro’s grandson, delivering a pointed warning that Cuba was running out of time to make changes Trump was demanding.

CIA director john ratcliffe in cuba
CIA Director John Ratcliffe visited Cuba in May to deliver Trump’s ultimatum to the island. (Image Credit: CIA via X/Reuters)

What Is the Task Force’s Objective

The task force’s stated mandate is to create fractures within Cuba’s political elite by targeting the financial and business dealings of its leadership. Officers will sift through newly collected intelligence to track money flows and shadow business activities both on and off the island.

The CIA could eventually release damaging financial information publicly to shift both elite and public opinion inside Cuba, a playbook it has used previously against Russia. The task force is also prohibited from enabling lethal operations, though that authority can be changed at any time by presidential directive.

What Are Trump’s Demands

Trump’s demands center on three broad areas: economic reform, political change, and leadership restructuring. Specifically, Washington wants Havana to replace what it considers anti-American hardliners with leaders more willing to engage with US interests. Beyond that, the New York Times article does not detail specific policy benchmarks or conditions Trump has formally set for the Cuban government.

Is a US Invasion of Cuba Imminent

Not immediately, but the groundwork is being laid. The fresh intelligence surge is being used to update US military planning options for potential action against Cuba should Trump choose that path.

Hawkish advisers inside the Trump administration have drawn direct lessons from Venezuela, where Trump successfully removed Nicolás Maduro and seized control of the country’s oil resources with speed that surprised even close observers. Some of those advisers privately believed Cuba’s government could fall before the US midterm elections in November.

However, the drawn-out war with Iran has absorbed the administration’s attention and resources, forcing Cuba hawks to acknowledge that any decisive move against Havana is likely on hold until the Iran conflict concludes.

(Note: Some images in this article are AI-generated)

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Mamoon Azeem
Mamoon Azeem
Mamoon is the founder and editor of The Spy Stories, a publication born from his unhealthy obsession with IR, Espionage, and Global Security. When he is not researching or writing about spies, double agents, and secret operations, Mamoon can usually be found hiking through remote mountain ranges and forests where he occasionally imagines himself on a covert mission far more exciting than reality.

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