Trump Gives Cuba Two-Week Ultimatum to Free Political Prisoners

The Trump administration has given Cuba a two-week ultimatum to release high-profile political prisoners, including dissident artists Luis Manuel Otero Alcántara and Maykel Osorbo, as part of secret negotiations held in Havana on April 10. The demand was delivered during the first visit by a U.S. delegation to the island since the normalization of relations under former President Barack Obama in 2016, according to reports by USA Today and Axios, citing sources close to the discussions. Otero Alcántara, who led the San Isidro Movement alongside Osorbo, was sentenced to five years in prison, while Osorbo received nine years for their roles in organizing the massive antigvernment protests of July 11, 2021, which gave rise to the dissident anthem "Patria y Vida." A State Department spokesperson confirmed to USA Today that President Trump remains committed to the release of all political prisoners and called the Cuban regime's attention to Trump's recent promise of a "new dawn for Cuba." The spokesperson stated that Cuba has "a small opportunity to reach a deal" and should cease what was described as "playing games" during negotiations. Axios reported that U.S. officials also met separately with Raúl Guillermo Rodríguez Castro, the grandson and trusted confidant of former dictator Raúl Castro, underscoring Washington's view that genuine negotiations must include figures within the regime. Beyond prisoner releases, discussions reportedly covered potential U.S. cooperation on Starlink satellite internet connectivity, possible dismantling of the six-decade-old economic embargo, and the need for greater political freedoms including free and fair elections. The ultimatum comes amid escalating pressure on Havana, which announced the pardon of 2,010 prisoners in early April and 52 more the previous month, though human rights organizations noted few consciousness prisoners among those freed. Cuba has maintained that such releases are routine rather than part of any deal with Washington. USA Today reported on April 15 that the Pentagon was quietly preparing military intervention options should Trump order action against the island located 90 miles from Florida. When questioned aboard Air Force One about the possibility of military action, Trump responded ambiguously, saying it "depends on how you define military action." U.S. officials have warned that Cuba's economy is "in free fall" and that the island's ruling elites have a narrow window to implement reforms before circumstances become irreversible, though the Cuban government has maintained a public stance emphasizing sovereignty while quietly engaging in the shadow negotiations.