Wednesday’s U.S. indictment of former Cuban President Raúl Castro, announced by federal prosecutors, landed amid months of intensified pressure and shifting diplomacy between President Donald Trump’s administration and Cuba’s socialist government. The case ties back to a 1996 incident involving Brothers to the Rescue, a Miami-based exile group, when two planes were shot down and Castro, then Cuba’s defense minister, allegedly played a role.
The indictment also reflects a broader campaign the AP described as part of Trump’s months-long effort to increase pressure on Cuba, including sanctions and economic measures that have worsened conditions on the island. AP said the administration escalated its rhetoric about regime change in Cuba after military action in Venezuela earlier this year ended with the capture of President Nicolás Maduro.
Trump’s approach toward Cuba unfolded alongside other major U.S. foreign-policy challenges, including an uneasy ceasefire in the U.S. war against Iran. Within that wider environment, the administration’s strategy toward Cuba relied on both legal action and intensified coercive pressure, while senior Cuban officials continued to publicly resist U.S. demands and threats.
In the months leading into the indictment, the tone between Washington and Havana sharpened. On Jan. 4, a day after the Venezuela operation that led to Maduro’s capture, U.S. Secretary of State Marco Rubio said Cuba’s government was “in a lot of trouble,” according to AP. On Jan. 11, Trump warned Cuba’s government as Venezuela’s close ally faced uncertainty, telling it “to make a deal BEFORE IT IS TOO LATE,” and Díaz-Canel responded that those “who turn everything into a business, even human lives, have no moral authority to point the finger at Cuba in any way, absolutely in any way.”
The administration’s policy moves were paired with new escalations in coercion. On Jan. 30, Trump signed an executive order to impose a tariff on goods from countries that sell or provide oil to Cuba, a step AP said could further cripple the island. AP also described a White House-ordered economic blockade that contributed to blackouts, food shortages and a collapse in Cuba’s economic activity.
Diplomatic signals continued to appear even as pressure mounted. AP reported that in March, Díaz-Canel said Cuba and the U.S. held talks, which he described as aimed at finding solutions through dialogue to bilateral differences, marking the first time Cuba confirmed widespread speculation about discussions with the Trump administration amid an energy crisis. Later in April, Reuters—via AP’s timeline—reported multiple senior contacts, including meetings in Havana that AP said involved U.S. officials with Raúl Guillermo Rodríguez Castro, the grandson of Raúl Castro and a central figure in Cuba’s political orbit despite not holding an official post.
The Cuban side also pressed back on the premises of U.S. engagement. On April 12, Díaz-Canel said in an interview he would not step down and that the U.S. had no valid reason to carry out a military attack against the island or attempt to depose him, according to AP’s account of his remarks on NBC’s “Meet the Press.” Later, at the United Nations, Cuban Ambassador Ernesto Soberón Guzmán told the AP in an interview that internal issues regarding detainees were “not on the negotiating table,” rejecting U.S. demands that included the release of political prisoners.
AP’s timeline also described how U.S. officials discussed humanitarian and economic offers while saying they were not looking at imminent military action. On May 7, U.S. officials told AP they were not seeking an imminent military operation against Havana despite Trump’s repeated threats that “Cuba is next” and discussions about potential U.S. warship deployments tied to Iran. Those officials also said they were not optimistic Cuba would accept an offer that included tens of millions of dollars in humanitarian aid, agricultural assistance and infrastructure support, along with two years of free Starlink internet access for all Cubans.
In the lead-up to the indictment, AP reported that the Justice Department was preparing to seek charges related to Raúl Castro’s alleged role in the 1996 shootdown, drawing attention to Brothers to the Rescue and Castro’s role as defense minister at the time. That reporting foreshadowed the formal charges announced by federal prosecutors on May 20, a timeline AP later corrected to reflect that two planes were shot down in 1996—not four.
By the end of the period described in AP’s account, the legal case had become the latest front in a widening contest between the U.S. and Cuba—one that has combined pressure and sanctions with intermittent diplomatic contacts, while both sides publicly laid out nonnegotiable positions ahead of the indictment.