Washington does not typically indict foreign heads of state, deploy carrier strike groups to the Caribbean, and dispatch its CIA director on a surprise visit to Havana in the same week. When it does all three simultaneously, while delivering a direct public address to the target nation’s population, the moves represent a coordinated strategic signal.
On May 14, CIA Director John Ratcliffe made a surprise visit to Havana, the highest-level American intelligence official to set foot on Cuban soil in decades. That same week, the Justice Department unsealed an indictment against Raul Castro, 94, for his involvement in the 1996 shoot-down of two civilian aircraft. Simultaneously, the USS Nimitz carrier strike group entered the southern Caribbean, and Secretary of State Marco Rubio delivered a pointed address directly to the Cuban people, bypassing the regime. This convergence marks the opening phase of a serious effort to force a fundamental reckoning in Havana.
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Raul Castro: The shadow ruler
While Miguel Diaz-Canel holds the formal titles of president and first secretary of the Communist Party, few serious analysts believe he wields real power. Decisive control remains with Castro and the Cuban military. Even after stepping down from formal roles, Castro retains the rank of army general and ultimate influence over the military elite.
Through its vast GAESA conglomerate, the Cuban military controls an estimated 60% of Cuba’s economy, including tourism, retail, agriculture, communications, and banking. This fusion of military and economic power makes the military the true backbone of the regime. Washington’s decision to indict Castro personally, and the reported participation of his grandson, Raulito, in meetings with Ratcliffe, signals that the United States understands exactly where power resides in Havana.
The pressure playbook
The current Cuba policy follows a pattern established elsewhere. In Venezuela, sustained economic pressure and targeted sanctions culminated in dictator Nicolas Maduro’s removal. In Iran, maximum pressure and strategic ambiguity led to decisive strikes that eliminated supreme leader Ali Khamenei. Cuba is now subject to the same logic: economic strangulation paired with a visible diplomatic off-ramp for those willing to negotiate a transition.
Cuba’s vulnerability became acute when Venezuelan oil supplies collapsed. Sweeping U.S. sanctions on third-country fuel suppliers under Executive Order 14380 have been devastating. The island now faces prolonged blackouts of 12 to 20 hours, acute food insecurity affecting nearly a third of the population, and a collapsing energy grid. After nearly seven decades of revolutionary rule, the Castro system is showing unmistakable signs of structural failure.
This approach represents a deliberate rejection of the Obama administration’s 2016 opening toward Cuba. That policy offered the regime economic relief and international legitimacy without requiring meaningful structural reforms. In the Trump administration’s view, it merely allowed Castro to manage a smooth transition of power to Diaz-Canel from a position of relative strength.
Rubio, whose family fled Cuba, has been blunt: Engagement without pressure only props up the dictatorship. His direct address to the Cuban people, offering a vision of a “worthy future,” is specifically designed to drive a wedge between the population and the ruling elite.
Deliberate ambiguity and coordinated pressure
The timing of these actions carries heavy geopolitical weight. On May 20, while Russian President Vladimir Putin and Chinese President Xi Jinping met in Beijing to project a united front against the U.S., Washington executed multiple moves in the Caribbean.
The Ratcliffe visit kept a diplomatic channel open, while the Castro indictment raised the personal legal stakes for the regime’s patriarch. The Nimitz deployment demonstrated hard power, and additional charges against Chinese nationals reinforced that foreign adversarial influence in the Western Hemisphere carries severe costs. This is the essence of the Trump doctrine in action: maintain maximum pressure while preserving calculated ambiguity, keeping adversaries uncertain about which front is decisive.
Risks and leverage
Cuba is not Venezuela. Its Intelligence Directorate remains one of the most sophisticated internal security services in the hemisphere, honed over decades to prevent organized opposition. Furthermore, the military has previously demonstrated resilience, notably during the economic collapse of the 1990s “Special Period.”
There are legitimate risks. A regime facing existential pressure could respond with mass repression or deliberately engineer another migration crisis reminiscent of the 1980 Mariel boatlift. There is also the danger that overly rigid pressure could push Cuba closer to Russia and China rather than toward accommodation.
Yet, the military’s extensive economic holdings through GAESA may create unique leverage. If senior officers can be assured of some protection for their interests in a post-Castro transition, the calculus inside the elite could shift.
The endgame
Domestic political dynamics provide additional context, with the midterm elections approaching. Florida’s Cuban American community, a key Republican constituency, has long demanded decisive action on Cuba. A tangible success in Havana before the elections would carry significant political weight, particularly in swing-state Latino communities.
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Cuba’s ruling elite now confronts the same choice previously faced by Maduro and Khamenei. The architecture of pressure — energy sanctions, naval presence, legal jeopardy for top leadership, and direct appeals to the population — is firmly in place. The question is whether Havana will conclude that the cost of continued defiance exceeds the cost of a managed transition.
The era of treating Cuba as a frozen Cold War artifact is over. Washington has signaled with unusual clarity that it intends to resolve this long-standing challenge in its own hemisphere. The ball is in Havana’s court, but time is rapidly running out.
Emzari Gelashvili is a former member of the Georgian Parliament and a former senior official in Georgia’s Ministry of Defense, Ministry of State Security, and Ministry of Internal Affairs, where his work focused on countering Russian and Iranian intelligence operations. He publishes national security analysis in RealClearDefense, the Hill, and Newsweek.