The Justice Department is preparing to seek an indictment of former Cuban leader Raúl Castro, a move that would escalate already heightened tensions between Washington and Havana as the island nation grapples with an energy crisis and the Trump administration's renewed pressure campaign. The potential indictment, which would require grand jury approval, is connected to Castro's alleged role in the 1996 shootdown of four planes operated by the Miami-based exile group Brothers to the Rescue, according to three people familiar with the matter who spoke on the condition of anonymity because they were not authorized to discuss an ongoing investigation.
The developments come as the United States has stepped up pressure on communist-controlled Cuba following military action in Venezuela early this year that resulted in the capture of President Nicolás Maduro. Castro was defense minister at the time of the 1996 incident. The Cuban government did not respond to a request for comment on the potential indictment, which was reported earlier by CBS.
Escalating Diplomatic and Economic Pressure
The timeline of recent U.S.-Cuba relations reveals a pattern of intensifying pressure tactics. 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 President Donald Trump renewed calls for an American takeover of the Danish territory of Greenland. On Jan. 11, Trump warned 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 already suffering from an energy crisis.
Behind-the-Scenes Negotiations
Despite the public hostility, back-channel talks have been underway. On Feb. 27, a day before the war in Iran began, 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 any details. Trump said Rubio was in discussions with Cuban leaders "at a very high level." 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.
Cuba Rejects Ultimatums
On April 9, Diaz-Canel said he would not resign. 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 in the interview on NBC's "Meet the Press," the president said an invasion of Cuba would be costly and affect regional security.
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.
Congressional Oversight Rejected
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.
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.
Intelligence-Level Engagement
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 are not optimistic the communist government will 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 has not yet outright refused the offer, which comes 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.
Why This Matters:
The escalating pressure on Cuba, including the potential indictment of a former leader and the energy blockade, directly impacts the lives of ordinary Cubans already struggling with fuel shortages and economic hardship. The rejection by Senate Republicans of legislation requiring congressional approval for the energy blockade demonstrates how unilateral executive action can bypass democratic oversight, allowing the administration to impose punitive measures that affect an entire population. The insistence on political prisoner releases as a precondition for talks, while humanitarian aid remains conditional, raises questions about whether U.S. policy prioritizes human rights or regime change. The involvement of intelligence agencies and the specter of military threats underscore how geopolitical maneuvering can overshadow the humanitarian needs of Cuban citizens, who bear the burden of both their government's policies and external sanctions.