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Cuba Becomes Washington’s New Intelligence Front

The CIA has created a targeted task force focused on Cuba as the Trump administration intensifies diplomatic, economic and intelligence pressure on Havana, raising fresh questions about the possibility of covert or military action.

4 mins read
File Photo of the US Military

The United States is intensifying its campaign against the Cuban government, with the Central Intelligence Agency establishing a targeted task force to gather intelligence, monitor financial activity linked to the Cuban political elite and develop an expanded strategy for exerting pressure on Havana.

The move marks a significant development in a campaign that has been building for months. American agencies, including the State Department, US Southern Command and the CIA, have increased monitoring, training and engagement surrounding Cuba since the beginning of 2026. The stated pressure has included demands for sweeping economic reforms, while the broader direction of the campaign increasingly points towards political change.

The task force, reportedly staffed by case officers, cyber specialists, intelligence analysts and covert field officers from across the intelligence community, provides the Trump administration with a mechanism to concentrate personnel, finances and technical resources on Cuba. Its reported objectives include political and leadership “changes” and efforts to fragment the power base of the Cuban government.

The emergence of the task force also reflects a shift in how Washington is approaching Havana. Rather than relying principally on conventional military pressure, the campaign is increasingly being driven through intelligence collection and influence operations designed to create political pressure from within Cuba.

The Soufan Center has been closely tracking this evolution. In its assessments of the US campaign against Cuba, the centre has described an expanding combination of diplomatic, economic and military pressure that has increasingly incorporated an intelligence-driven component. Its analysis places the latest CIA initiative within a broader campaign that has already included sanctions and maritime embargoes affecting oil shipments bound for Cuban markets.

Those measures have contributed to severe economic pressure on Cuba. The Cuban economy has fallen further into crisis, with shortages affecting basic services, medicines, fuel and foodstuff. The pressure has coincided with a sweeping economic reform package introduced in July that overturns many government monopolies across different economic sectors, opening greater space for private-sector actors and liberalising parts of the Cuban economy.

Economic reform, however, appears to represent only one part of Washington’s broader objectives. US Secretary of State Marco Rubio has described major economic reforms as an objective of the pressure campaign, but the campaign has increasingly taken aim at the political structure itself. The emerging strategy seeks not merely to alter Cuba’s economic system but to weaken the political elite and shape a more pragmatic government in its place.

That shift has also been reflected in the nature of direct US engagement with Cuban officials. Since the early months of 2026, contacts involving US and Cuban officials, particularly those concerning Raúl Castro’s grandson and major economic player Raúl Guillermo Rodríguez Castro, have increasingly moved from the State Department towards US intelligence agencies.

The transition became particularly visible in May, when CIA Director John Ratcliffe made a rare public visit to Havana to convey a message from the White House to Cuban military and intelligence officials. The visit was followed by increased US drone surveillance and a larger American intelligence presence on the island.

Reports of intensified intelligence activity have since continued. The CIA has reportedly expanded local recruitment of foreign officers, while paving the way for political change in Cuba has emerged as a priority for Secretary Rubio. During the same month, Washington raised Cuba’s position within its National Intelligence Priorities Framework, reclassifying the country as a “Priority 1” target. Cuba now shares that status with Russia, Iran and China.

The escalation has been accompanied by an effort to establish a broader narrative around Cuban activities and to shape public support for a more assertive American response. The Soufan Center has also highlighted this element of the campaign.

Just weeks before reports emerged about the CIA task force, the State Department released a 99-page report titled “Cuba: The Capital of 21st Century Communism”. The report detailed what it described as decades of Cuban clandestine intelligence and political influence operations inside the United States. It also drew links between Cuban intelligence officers, nonprofit organisations and activists and several US “upheavals” and leftist political movements, including the George Floyd protests, “the rise of Antifa” and “pro-terrorist activism on American college campuses”.

The emergence of the CIA task force therefore represents another stage in an increasingly comprehensive pressure campaign. The approach shares elements with the Trump administration’s previous escalation involving Venezuela and Iran, but the methods being applied to Cuba appear different.

In Venezuela and Iran, the administration pursued campaigns involving military assets, air strikes, surveillance, intelligence collection and special extraction operations. In Cuba, the emphasis is increasingly on intelligence collection, recruitment and influence operations intended to encourage political change from within rather than relying principally on force from outside.

The ultimate objective described in the source material is regime change, although direct military intervention remains uncertain. The establishment of the task force does not necessarily mean that Washington has decided to launch a military operation. Intelligence operations can encompass a wide range of activities, including influence campaigns designed to weaken or fragment a government without attempting to overthrow it directly.

As intelligence expert Marc Polymeropoulos has noted, covert action does not necessarily translate into a coup d’état: “it can mean influence operations.”

Nevertheless, the possibility of military action remains part of the wider calculation. Any American intervention in Cuba would take place against the backdrop of continuing conflict in the Middle East and competing US strategic priorities in Europe and the Pacific. The United States is already facing pressure on its munitions capacity, raising questions about how much additional strain a new theatre could place on the defence industrial complex.

The military balance between Washington and Havana is heavily tilted towards the United States. But an operation intended as a rapid decapitation mission rather than a conventional sustained campaign would still carry the possibility of an asymmetric ground conflict involving Cuban guerrilla militias.

Domestic political considerations could further complicate any decision. With midterm elections approaching, a two-front American military effort involving the Middle East and the Caribbean could impose substantial political costs on the Trump White House.

For Washington, the challenge is therefore no longer simply whether to increase pressure on Havana, but how far that pressure can be taken without creating consequences that become more difficult to control. Any military campaign or influence operation that fails could carry economic, security and political costs, particularly given Cuba’s proximity to the United States.

The CIA task force signals that Washington is preparing for a more sustained contest over Cuba’s political future. But whether intelligence pressure produces political transformation, intensifies confrontation or ultimately creates a path towards direct intervention remains unresolved.

What is clear is that Cuba has moved considerably higher on Washington’s strategic agenda. The shift towards an intelligence-led campaign suggests that the United States is attempting to achieve through pressure, recruitment and influence what previous approaches sought to accomplish through more overt forms of coercion. The outcome will depend not only on the resources Washington commits, but on its ability to sustain a long-term strategy while managing simultaneous pressures far beyond the Caribbean.

Sri Lanka Guardian

The Sri Lanka Guardian is an online web portal founded in August 2007 by a group of concerned Sri Lankan citizens including journalists, activists, academics and retired civil servants. We are independent and non-profit. Email: editor@slguardian.org

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