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The administration of Donald Trump is applying the same maximum pressure strategy against Cuba that it used to force change in Venezuela: progressive sanctions, threats of legal action, and direct negotiation through the CIA director as the president's personal messenger, according to an analysis published by El País.
On Wednesday, May 14, John Ratcliffe, director of the Central Intelligence Agency, traveled to Havana without prior announcement and met face to face with the head of the Intelligence Directorate of the Ministry of the Interior, Ramón Romero Curbelo; the minister of the Interior, Lázaro Álvarez Casas; and the grandson of Raúl Castro, Raúl Rodríguez Castro.
The meeting took place on the same day the regime publicly acknowledged the depletion of its last fuel reserves, amid widespread power outages and popular protests.
The message that Ratcliffe brought to Havana was clear: Washington demands "fundamental changes to seriously address economic and security issues," and Cuba "cannot be a refuge for the enemies of the United States in the Western Hemisphere."
In return, the State Department officially reiterated the offer of 100 million dollars in humanitarian aid, contingent upon those reforms. The CIA also warned that "the window of opportunity will not remain open indefinitely."
The parallel with Venezuela is explicit.
In January 2026, Ratcliffe traveled to Caracas to meet with the acting president Delcy Rodríguez—following the military capture of Nicolás Maduro in the so-called "Operation Absolute Resolution"—with a nearly identical message: comply with Washington's instructions or face a fate "worse" than that of his predecessor.
He also warned him then that Venezuela "cannot be a refuge for the adversaries of the United States, especially drug traffickers."
Trump had foreshadowed the tone of the discussions on May 12 with a post on his social media: "Cuba is asking for help, and we are going to talk!"
The legal threat reinforces the narrative. Simultaneously with the revelation of Ratcliffe's visit, representatives from the Department of Justice announced that they are preparing formal charges against Raúl Castro, 94, for his role in the downing of two Brothers to the Rescue planes on February 24, 1996, resulting in the deaths of four Cuban Americans: Carlos Costa, Mario de la Peña, Luis Salcines, and Armando Alejandre Jr.
The accusation, which could be presented around May 20, directly evokes the legal strategy used 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 Department of Justice supporting this step.
The energy context surrounding the entire negotiation is one of unprecedented collapse. On May 13, Díaz-Canel reported an impact on the electrical system of 2,113 MW, a new annual record, with blackouts of up to 24 hours in some provinces.
Trump's sanctions since January 2026 have worsened the crisis: Executive Order 14380, signed on January 29, tightened secondary sanctions on the oil supply to Cuba, and on May 1, a new order expanded restrictions on energy, defense, mining, and finance.
This Monday, the Treasury sanctioned 11 individuals and three additional Cuban entities, including the Minister of Energy, the Minister of Communications, and the National Revolutionary Police.
Unlike the thawing in 2015—when then-CIA director John Brennan also visited Havana secretly following negotiations mediated by the Vatican, a visit that Washington never officially acknowledged—this time both governments publicly confirmed the meeting immediately, underscoring the nature of the operation: it is not a discreet opening, but rather an explicit and calculated pressure.
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