CIA Director John Ratcliffe met with senior Cuban officials in Havana on Thursday, only the second known visit to the island by a sitting head of U.S. intelligence since the 1959 revolution, hours before U.S. media outlets reported that the Justice Department is preparing to indict former Cuban President Raul Castro and as the State Department publicly restated a $100 million humanitarian aid offer.
The three moves, executed within a 24-hour window, mark the most aggressive U.S. push on Havana since President Trump returned to office. Cuba's grid has collapsed under a Trump-imposed fuel blockade, with rolling blackouts of up to 22 hours a day and the energy minister conceding Wednesday that the island has no diesel or fuel oil in reserve. Washington is now testing whether pressure, prosecution and a conditional aid package can force what the administration calls "fundamental changes" in the communist government.
The Havana meeting
Ratcliffe sat down with Interior Minister Lazaro Alvarez Casas, the head of Cuba's intelligence services and Raulito Rodriguez Castro, the grandson of Raul Castro, according to a CIA official cited by NBC News and Fox News. The CIA posted photographs of Ratcliffe in the Cuban capital without further explanation. A Cuban government statement said both sides "underscored their interest in developing bilateral cooperation between law enforcement agencies."
The CIA official said Ratcliffe was there "to personally deliver President Trump's message that the United States is prepared to seriously engage on economic and security issues, but only if Cuba makes fundamental changes." Havana used the meeting to argue, as it has for years, that the country poses no threat to U.S. national security and does not belong on the State Department's list of state sponsors of terrorism, a designation the Biden administration lifted in January 2025 and Trump reinstated on his first day back in office.
The indictment track
While Ratcliffe was in Havana, Reuters and other outlets reported that federal prosecutors in the Southern District of Florida are moving toward charging the 94-year-old Castro over Cuba's 1996 shootdown of planes flown by the anti-Castro humanitarian group Brothers to the Rescue. Any indictment would require approval from a grand jury, Al Jazeera reported, and would mark a sharp escalation against a figure who remains, by Cuban and outside accounts, the country's most powerful man.
The aid carrot
The State Department said Wednesday it would deliver $100 million in direct humanitarian assistance, routed through the Catholic Church and other independent groups, if Havana accepts reforms. Secretary of State Marco Rubio told NBC's Tom Llamas the only condition is that the funds bypass the government: "This can't be humanitarian aid that the government steals for itself." Cuban President Miguel Diaz-Canel signaled Thursday on X that Cuba would not refuse aid "in full conformity with the universally recognized practices for humanitarian assistance," while calling the offer paradoxical from a country that "punishes" the Cuban people through the embargo. Foreign Minister Bruno Rodriguez said Havana wanted to hear the details.
Backdrop
The pressure campaign rests on the January U.S. military operation that removed Venezuelan President Nicolas Maduro, cutting off the oil supply that had kept Cuban power stations running. Trump has since threatened tariffs on any country that ships oil to the island, producing a de facto fuel blockade. CNN reported the U.S. military has flown dozens of intelligence-gathering missions near Cuba's largest cities since February.
The counterpoint
Fox News framed the Havana visit as a "rare chance" for Cuba to stabilize before Trump enforces redlines. Al Jazeera and NBC News reported the same events as collective punishment of an 11-million-person population already without fuel, food and medicine, and noted that the administration has privately pressed Diaz-Canel to step aside, a move that would still leave the communist leadership in place. Rodriguez told NBC the U.S. offer carried "the incongruity of this apparent generosity from a party that subjects the Cuban people to collective punishment through economic warfare."
A grand jury vote on the Castro indictment has not been scheduled publicly. Cuban officials said Thursday they were awaiting details on how the $100 million would be delivered.