Summary

The U.S. announced a grand jury indictment of former Cuban President Raúl Castro on May 20, adding to a months-long campaign of pressure and legal action against the Cuba’s socialist-controlled government during President Donald Trump’s second term. The indictment was described as tied to Raúl Castro’s alleged role in a 1996 incident involving the shootdown of two planes run by the Miami-based exile group Brothers to the Rescue, when Castro was defense minister, according to the Associated Press timeline.

The developments also unfolded alongside heightened rhetoric from Washington and public responses from Havana, as well as repeated contacts between U.S. officials and Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro, amid Cuba’s energy and economic strain. The U.S. push came while the Trump administration faced a separate, uneasy ceasefire in its war against Iran, the Associated Press said.

In early January, the timeline described Secretary of State Marco Rubio declaring Cuba’s government was “in a lot of trouble” in comments made a day after Venezuela’s leader Nicolás Maduro was captured in a military operation earlier in the year. It said Trump then warned Cuba in mid-January, calling for the government “to make a deal BEFORE IT IS TOO LATE,” and that Díaz-Canel responded that people who turn “everything into a business, even human lives” had “no moral authority” to point at Cuba.

As the year progressed, the Associated Press timeline also described steps aimed at squeezing Cuba’s economy. It said Trump signed an executive order on Jan. 30 to impose a tariff on goods from countries that sell or provide oil to Cuba, and it described an economic blockade that had led to blackouts, food shortages and economic collapse. In late February, it said Trump raised the possibility of a “friendly takeover of Cuba” and said Rubio was in discussions with Cuban leaders “at a very high level.”

While the pressure intensified, Cuba and the U.S. also explored channels of communication. The timeline said Díaz-Canel confirmed in March that Cuba and the U.S. held talks for the first time in years, describing them as aimed at “finding solutions through dialogue” to bilateral differences. It also said that at least one U.S. official met with Rodríguez Castro earlier in April and that two senior State Department officials—Jeremy Lewin and Michael Kozak—led a delegation to Havana and met Rodríguez Castro, according to a U.S. official familiar with the meetings.

The Associated Press timeline also detailed how Cuba’s leadership publicly rejected the possibility of U.S. coercion. It said Díaz-Canel told NBC’s “Meet the Press” on April 12 that he would not step down and that the U.S. had no valid reason to carry out a military attack or attempt to depose him, with the president adding that an invasion would be costly and affect regional security. During a rally marking the 65th anniversary of the Cuban Revolution’s socialist essence, the timeline said Díaz-Canel warned the country was facing “serious threats, including military aggression” and said Cuba was duty-bound to prepare.

On April 17, the timeline said news emerged that an American delegation recently met with Cuban officials, described as the third meeting with Rodríguez Castro. It said a senior State Department official met earlier in the month and that Rubio was not part of the Havana delegation, with one U.S. official speaking on condition of anonymity.

Alongside those diplomatic contacts, Cuba also rejected key U.S. demands tied to political prisoners. The timeline said a Cuban diplomat speaking at the United Nations said Havana would not abide by U.S. “ultimatums” to release political prisoners as part of new talks, citing comments by Cuban Ambassador to the U.N. Ernesto Soberón Guzmán in an Associated Press interview that detainees’ internal issues “are not on the negotiating table.”

The Associated Press timeline then described how U.S. officials simultaneously advanced pressure through sanctions and intelligence cooperation. It said a Senate vote showed Republicans rejecting Democratic legislation requiring congressional approval for Trump to end the U.S. energy blockade on Cuba. It also said that on May 14, CIA Director John Ratcliffe met Cuban officials including Rodríguez Castro, Interior Minister Lázaro Álvarez Casas and the head of Cuban intelligence services, and that CIA officials confirmed the meetings to the Associated Press.

The legal shift that followed was described as the latest step. It said the Justice Department was preparing to seek an indictment against Castro, with three people familiar with the matter telling the AP that the potential indictment related to Castro’s alleged role in the 1996 shootdown of two Brothers to the Rescue planes. On May 20, it said federal prosecutors announced a grand jury indictment, and the Associated Press timeline noted that it had been corrected to reflect that two planes, not four, were shot down in 1996.