The Trump administration is implementing a strategy of maximum pressure against Cuba, mirroring the approach used to instigate change in Venezuela. This involves escalating sanctions, threats of legal action, and direct negotiations facilitated by the CIA director acting as a personal envoy for the president, according to an analysis by El País.
On Wednesday, May 14, CIA Director John Ratcliffe made an unannounced visit to Havana. He met with Ramón Romero Curbelo, head of the Ministry of the Interior's Intelligence Directorate; Lázaro Álvarez Casas, the Minister of the Interior; and Raúl Rodríguez Castro, the grandson of Raúl Castro.
The meeting coincided with the regime's public admission of its dwindling fuel reserves, amidst widespread power outages and public protests.
Ratcliffe delivered a straightforward message to Havana: Washington demands "fundamental changes to seriously address economic and security issues," and Cuba "cannot serve as a haven for enemies of the United States in the Western Hemisphere."
In return, the State Department officially reiterated an offer of $100 million in humanitarian aid, contingent upon these reforms. The CIA further warned that "the window of opportunity will not remain open indefinitely."
The parallels with Venezuela are overt.
Back in January 2026, Ratcliffe traveled to Caracas to meet with interim President Delcy Rodríguez—following the military capture of Nicolás Maduro during "Operation Absolute Resolution"—delivering a nearly identical message: comply with Washington's directives or face a fate "worse" than that of her predecessor.
He also warned her that Venezuela "cannot be a refuge for adversaries of the United States, especially drug traffickers."
President Trump had foreshadowed the tone of these communications on May 12 with a post on his social media: "Cuba is asking for help, and we are going to talk!"
The threat of legal action strengthens the strategy. Along with the revelation of Ratcliffe's visit, Justice Department representatives announced they are preparing formal charges against Raúl Castro, now 94, for his role in the downing of two Brothers to the Rescue planes on February 24, 1996, which resulted in the deaths of four Cuban-Americans: Carlos Costa, Mario de la Peña, Luis Salcines, and Armando Alejandre Jr.
This indictment, potentially to be filed around May 20, directly evokes the judicial strategy employed against Maduro and responds to sustained pressure from Senator Rick Scott and Cuban-American congress members Carlos Giménez, Mario Díaz-Balart, and María Elvira Salazar, who sent a formal letter to the Justice Department supporting this action.
The energy context surrounding the negotiations is one of unprecedented collapse. On May 13, Díaz-Canel reported a 2,113 MW impact on the electrical system, setting a new annual record, with blackouts lasting up to 24 hours in some provinces.
Trump's sanctions since January 2026 have exacerbated the crisis: Executive Order 14380, signed on January 29, tightened secondary sanctions on oil supplies to Cuba, and on May 1, a new order expanded restrictions to energy, defense, mining, and finance.
This Monday, the Treasury Department sanctioned 11 additional Cuban individuals and three entities, including the Minister of Energy, the Minister of Communications, and the Revolutionary National Police.
Unlike the thaw of 2015—when then-CIA Director John Brennan also made a secret trip to Havana following Vatican-mediated negotiations, a visit Washington never officially acknowledged—this time both governments immediately confirmed the meeting publicly, underscoring the nature of the operation: it is not a discreet opening, but an explicit and calculated pressure campaign.
Key Questions About U.S. Strategy in Cuba
What is the main strategy of the Trump administration toward Cuba?
The Trump administration is using a strategy of maximum pressure, similar to that used in Venezuela, involving sanctions, legal threats, and direct negotiations through the CIA director.
What was the outcome of John Ratcliffe's visit to Havana?
Ratcliffe conveyed a message demanding significant reforms from Cuba in exchange for potential humanitarian aid from the U.S., emphasizing that the opportunity for cooperation will not last indefinitely.
How does the current strategy differ from the U.S. approach in 2015?
Unlike the secretive negotiations of 2015, the current approach is openly acknowledged by both the U.S. and Cuban governments, marking a shift towards a more overt pressure campaign.