Wednesday’s U.S. indictment of former Cuban President Raúl Castro is the latest step in a Trump administration campaign that has combined heightened rhetoric about Cuba with expanded sanctions, even as the two governments have at times signaled possible dialogue. Federal prosecutors announced the grand jury indictment on May 20, charging Castro for his alleged role in the 1996 shootdown of two planes operated by the Miami-based exile group Brothers to the Rescue, according to the Associated Press timeline.
The AP timeline shows the pressure campaign building across the early months of the Trump administration’s second term. A day after the operation in Venezuela that captured President Nicolás Maduro, Secretary of State Marco Rubio said Cuba’s government was “in a lot of trouble,” while President Donald Trump renewed calls for an American takeover of Greenland. In mid-January, Trump warned Cuba’s government to “make a deal BEFORE IT IS TOO LATE,” as Díaz-Canel responded by saying those who turn “everything into a business, even human lives” lacked moral authority to point at Cuba.
As the administration’s approach tightened, Trump signed an executive order on Jan. 30 imposing a tariff on goods from countries that sell or provide oil to Cuba, a step described as potentially crippling for the island. On Feb. 27, as the U.S. prepared for its war against Iran, Trump said the U.S. was in talks with Havana and raised the possibility of a “friendly takeover of Cuba,” without offering details, and said Rubio was in discussions with Cuban leaders “at a very high level.”
The timeline also documents meetings between U.S. officials and Raúl Guillermo Rodríguez Castro, known as “Raúlito,” as Cuba and the United States moved along a parallel track of backchannel diplomacy. The AP reported that “Raúlito” secretly met with Rubio in February on the sidelines of a Caribbean Community summit in St. Kitts, and that Cuba’s President Miguel Díaz-Canel later confirmed talks with the U.S. on March 13, saying the discussions were aimed at finding solutions through dialogue. In April, an AP report said two senior State Department officials — Jeremy Lewin, who is in charge of all U.S. foreign assistance, and Michael Kozak, the top U.S. diplomat for Latin America — met with Rodríguez Castro in Havana, citing a U.S. official familiar with the meetings.
During that same period, Cuban leaders rejected certain U.S. conditions. On April 23, Cuban Ambassador to the United Nations Ernesto Soberón Guzmán told The Associated Press that internal issues regarding detainees “are not on the negotiating table,” describing those matters as not being part of the negotiation agenda. Cuba’s stance came as U.S. talks were reported as involving a key demand for the release of political prisoners, according to the timeline.
As the dialogue signals and public pressure overlapped, the Trump administration continued adding sanctions. On May 18, the State Department imposed a new layer of sanctions on several Cuban government agencies, including the Interior Ministry and National Police and Intelligence Directorate, as the campaign against the island continued to intensify. At the same time, U.S. officials continued high-level contact: the AP said CIA Director John Ratcliffe met with Cuban officials during a high-level visit on May 14, including Rodríguez Castro, Interior Minister Lázaro Álvarez Casas, and the head of Cuban intelligence services, and that a CIA official confirmed the meetings.
The indictment announcement on May 20 followed a report that prosecutors were preparing to seek charges against Castro. The AP timeline says the Justice Department was preparing to seek an indictment, with three people familiar with the matter speaking to the AP on May 15 on condition of anonymity. It also notes that the investigation connected to Castro’s alleged role in the 1996 shootdown of two planes, and that the Cuban government did not respond to a request for comment on the potential indictment, which the timeline says was earlier reported by CBS.
As this legal pressure has escalated, the broader geopolitical context has continued to shape U.S. attention. The AP timeline says the tensions between the Trump administration and Cuba’s government have risen alongside an uneasy ceasefire in the U.S. war against Iran. While officials continued probing possible diplomatic engagement with Havana and negotiating signals appeared in public comments and interviews, the May 20 indictment underscores that the administration’s strategy has also relied on expanding pressure through sanctions and legal action.
The timeline concluded with a correction: it says the 1996 shootdown involved two planes, not four. It is against that updated detail that the U.S. indictment was announced on May 20.