The Press Junction.
The Press Junction.
18 May 2026

Trump administration steps up pressure on Cuba

© Alexander Kunze via Unsplash

The Trump administration is stepping up its pressure on Cuba, including reconnaissance flights, an energy embargo and a much-discussed visit by CIA Director John Ratcliffe to Havana.

Officials are also discussing a possible federal indictment of former Cuban President Raúl Castro, possibly for drug trafficking or his role as then Defense Minister in Cuba's 1996 shooting down of two civilian aircraft, killing four people.

The visit by John Ratcliffe, only the second intelligence director to visit Cuba since it became communist in 1959, mirrors the strategy employed against Nicolás Maduro of Venezuela. The latter was detained in January following a U.S. federal indictment during a U.S. military raid.

Although a similar military operation against the frail, 90-year-old Castro is considered unlikely, senior U.S. officials want to keep the option open. They believe the threat alone could pressure Havana to make concessions, particularly in terms of closing Chinese and Russian intelligence posts on the island.

Experts are skeptical about the chances of this approach succeeding. Political science professor William LeoGrande of American University describes the possible indictment to The New York Times as an additional means of pressure: Trump and Rubio are trying to force Cuba to make concessions at the negotiating table through the threat of military intervention. But, he warns, "Cubans are not particularly inclined to give in."

Others suggest that the indictment is mostly a symbolic gesture aimed at the influential Cuban-American community in Miami, rather than a real step toward regime change.

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