Timeline of recent US-Cuba relations amid heightened tensions in Trump’s second term

The U.S. has intensified its stance toward Cuba following the January 2024 military operation in Venezuela that led to the capture of President Nicolás Maduro. The Justice Department is preparing to seek an indictment against former Cuban leader Raúl Castro, a move requiring grand jury approval and likely to heighten tensions with Havana. Trump’s administration has also imposed tariffs on goods from countries supplying oil to Cuba, further straining the island’s economy. In January, Secretary of State Marco Rubio warned Cuba’s government was 'in a lot of trouble' after Maduro’s removal, while Trump urged Havana to 'make a deal before it is too late.' Cuban President Miguel Díaz-Canel rejected U.S. moral authority, calling its actions hypocritical. By late January, Trump signed an executive order targeting oil shipments to Cuba, exacerbating economic pressures. In late February, Trump hinted at a potential 'friendly takeover' of Cuba, claiming high-level talks were underway with Cuban leaders through Rubio. Around the same time, Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro, met secretly with Rubio during a Caribbean summit in St. Kitts. These discussions marked the first confirmed diplomatic exchanges between the two nations amid Cuba’s energy crisis. By mid-March, Díaz-Canel confirmed that Cuba and the U.S. had engaged in talks, acknowledging speculation about negotiations. The exchanges occurred as Trump’s administration maintained a hardline approach, balancing Cuba relations with ongoing tensions in Iran and Venezuela. The evolving situation reflects a critical juncture in U.S.-Cuba relations under Trump’s second term.