Federal prosecutors announced a grand jury indictment against former Cuban President Raúl Castro in connection with the 1996 shootdown of two planes operated by the Miami-based exile group Brothers to the Rescue, marking a significant escalation in the Trump administration's pressure campaign against Cuba's socialist-controlled government. Castro, who served as defense minister at the time of the attack 30 years ago, now faces U.S. criminal charges for his alleged role in the incident.
The indictment represents the latest development in months of intensifying economic and diplomatic pressure following the capture of Venezuelan President Nicolás Maduro early this year. A White House-ordered economic blockade has led to blackouts, food shortages and a collapse in economic activity across Cuba.
Escalating Diplomatic Pressure
On Jan. 4, a day after the operation in Venezuela that captured Maduro, Secretary of State Marco Rubio declared Cuba's government was "in a lot of trouble," as the president renewed calls for an American takeover of the Danish territory of Greenland. On Jan. 11, Trump fired off a warning to the government of Cuba as the close ally of Venezuela braced for potential unrest after Maduro was deposed. Trump called for the Cuban government "to make a deal BEFORE IT IS TOO LATE."
Cuba's president, Miguel Díaz-Canel, responded, "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."
On Jan. 30, Trump signed an executive order to impose a tariff on any goods from countries that sell or provide oil to Cuba, a move that could further cripple the island. On Feb. 27, Trump said the U.S. was in talks with Havana and raised the possibility of a "friendly takeover of Cuba," though he did not offer details. Trump said Rubio was in discussions with Cuban leaders "at a very high level."
Secret Diplomatic Channels
Sometime in February, Raúl Guillermo Rodríguez Castro, the grandson of Castro known as "Raúlito," secretly met with Rubio on the sidelines of a Caribbean Community summit in St. Kitts. On March 13, Díaz-Canel said Cuba and the U.S. held talks, marking the first time the Caribbean country confirmed widespread speculation about discussions with the Trump administration amid an energy crisis. He said the talks "were aimed at finding solutions through dialogue to the bilateral differences between our two nations. International factors facilitated these exchanges."
On March 31, a sanctioned Russian oil tanker arrived in Cuba, the first time in three months fuel reached the island. On April 9, Díaz-Canel said he would not resign. On April 10, 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 — led a delegation to Havana and met with Rodríguez Castro, according to one U.S. official familiar with the meetings.
On April 12, Díaz-Canel said in an interview he would not step down and that the U.S. has no valid reason to carry out a military attack against the island or to attempt to depose him. Speaking on NBC's "Meet the Press," he said an invasion of Cuba would be costly and affect regional security.
Cuban Resistance to U.S. Demands
On April 16, Díaz-Canel spoke during a rally that drew hundreds of people to commemorate the 65th anniversary of the declaration of the Cuban Revolution's socialist essence. "The moment is extremely challenging and calls upon us once again, as on April 16, 1961, to be ready to confront serious threats, including military aggression. We do not want it, but it is our duty to prepare to avoid it and, if it becomes inevitable, to defeat it," Díaz-Canel said.
On April 17, news emerged that an American delegation recently met with Cuban government officials, marking a renewed diplomatic push. This was at least the third meeting with Rodríguez Castro. A senior State Department official met with Rodríguez Castro earlier in the month, according to a department official, who was not authorized to comment publicly and spoke on condition of anonymity to discuss the sensitive matter. The official did not say who from the U.S. met with Rodríguez Castro, whose grandfather is believed to play an influential role in the Cuban government despite not holding an official post. A second U.S. official said Rubio was not part of the delegation that visited Havana.
On April 23, a Cuban diplomat speaking at the United Nations said Havana will not abide by any American "ultimatums" to release political prisoners as part of new talks. In an interview with The Associated Press, Cuban Ambassador to the U.N. Ernesto Soberón Guzmán said internal issues regarding detainees "are not on the negotiating table." The release of political prisoners was a key U.S. demand as the longtime adversaries held discussions in Cuba for the first time in a decade.
Congressional and Intelligence Developments
On April 28, Senate Republicans rejected legislation from Democrats that would have required Trump to end the U.S. energy blockade on Cuba unless he receives approval from Congress. The vote on the war powers resolution showed how Republicans continue to stand behind Trump as he acts unilaterally to exert American force in a range of global conflicts, including Venezuela, Iran and Cuba — one of the U.S.'s closest neighbors.
On May 7, U.S. officials said the United States was not looking at imminent military action against Havana despite Trump's repeated threats that "Cuba is next" and that American warships deployed in the Middle East for the Iran conflict could return by way of the island. The officials involved in preliminary discussions with Cuban authorities also said they were not optimistic the communist government would accept an offer for tens of millions of dollars in humanitarian aid, two years of free Starlink internet access for all Cubans, agricultural assistance and infrastructure support. But they said Cuba had not yet outright refused the offer, which came with conditions that the government has long resisted, even after the Trump administration imposed new sanctions on Havana.
On May 14, U.S. and Cuban officials said CIA Director John Ratcliffe met with Cuban officials including Raúl Castro's grandson during a high-level visit to the island. Ratcliffe met with Rodríguez Castro, Interior Minister Lázaro Álvarez Casas and the head of Cuban intelligence services, and discussed intelligence cooperation, economic stability and security issues. A CIA official confirmed the meetings to the AP.
Path to Indictment
On May 15, the Justice Department was preparing to seek an indictment against Castro, three people familiar with the matter told the AP. One of the people said the potential indictment was connected to Castro's alleged role in the 1996 shootdown of two planes operated by the Miami-based exile group Brothers to the Rescue. Castro was defense minister at the time. All three people spoke on the condition of anonymity because they were not authorized to discuss an ongoing investigation. The Cuban government did not respond to a request for comment on the potential indictment, which was reported earlier by CBS.
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 Trump administration continued to ratchet up pressure against the island.
Why This Matters:
The indictment of a former head of state for actions taken 30 years ago demonstrates the administration's commitment to holding authoritarian regimes accountable for attacks on American citizens and allies. The timing—amid ongoing diplomatic engagement and economic pressure—signals that negotiations proceed from a position of strength, not accommodation. Cuba's refusal to release political prisoners despite offers of substantial economic assistance reveals the limits of diplomacy with authoritarian governments that prioritize regime survival over citizen welfare. The economic blockade's effectiveness in generating internal pressure, evidenced by widespread shortages and the regime's desperate outreach to Russia for fuel, underscores the utility of targeted economic measures as alternatives to military intervention. Senate Republicans' rejection of restrictions on executive authority preserves presidential flexibility in responding to threats in America's hemisphere, where Cuban influence has long destabilized democratic neighbors.