US imposed 2-week deadline during secret Cuba meeting

The U.S. has told Cuba that it has two weeks to let go of high-profile political prisoners as a sign of good faith.

A source who knows about the meeting said that the demand was made at a secret meeting in Cuba on April 10.

Luis Manuel Otero Alcántara and Maykel Osorbo, two dissident artists from the San Isidro movement who were sentenced in 2022, were among the names that were brought up for release.

A State Department spokesperson told USA TODAY that the Trump administration is still committed to freeing all political prisoners, including Alcántara and Osorbo.

The spokesperson pointed to Trump's remarks at an April 17 rally that a "new dawn for Cuba" is coming and said the regime should stop playing games as direct talks are occurring. The Cuban government has a small window to make a deal, the person said.

Regime change? A military takeover? Trump's thorny Cuba options

A senior State Department delegation traveled to Cuba on April 10 for talks with the government, a State Department official confirmed to USA TODAY. A senior State Department official also had a separate meeting with former Cuban leader Raul Castro's grandson during the visit, the person said.

It was the first time that a U.S. government plane had landed in Cuba since 2016. Axios was the first news outlet to report that the meetings took place.

The officials told the Cuban government that the island's economy is in free fall and its ruling elites had a narrow window to make reforms before circumstances irreversibly worsen, the State Department official said. The person said that Trump is committed to pursuing a diplomatic solution, if one is possible, but will not let allow the island to collapse into what he views as a major national security threat, if Cuba’s leaders are unwilling or unable to act.

At the meeting, the U.S. proposed to bring Starlink's high-speed internet services to Cuba. But the officials said Havana needs to enact reforms that will make Cuba's economy more competitive and attractive to foreign investment. They also pushed for compensation of Americans and American-owned businesses that had their property confiscated and a lifting of constraints on political freedoms.

Exclusive: Pentagon ramps up planning for possible military ops in Cuba
Released prisoner Roelvis Saname, 26, leaves La Lima penitentiary as part of the amnesty for more than 2,000 prisoners that the communist-run government has announced amid talks with the administration of U.S. President Donald Trump, Havana, Cuba, April 3, 2026. REUTERS/Norlys Perez TPX IMAGES OF THE DAY
It was after that meeting that Castro's grandson, Raúl Guillermo Rodríguez Castro, tapped a Cuban businessman to personally bring a letter to the White House, bypassing official channels.

The man, Roberto Carlos Chamizo González, was intercepted in Miami, as first reported by the Wall Street Journal.

Tensions have been escalating between the U.S. and Havana for weeks, with Trump warning of the potential for a hostile takeover. After capturing Venezuela's leader in January, the Trump administration tightened longstanding sanctions and oil shipments to Cuba as part of a broader campaign to force sweeping political changes on the communist-run island. Already mired in a severe economic crisis, the near-total blockade is pushing the country toward collapse.

In recent weeks, Trump has said he believed he'd have the "honor of taking Cuba" and the U.S. "may stop by Cuba" after it finishes with Iran.

The U.S. has said in the last few days that Trump is still thinking about his options. On April 15, USA TODAY said that the military was making plans for a possible If Trump decides to step in, the Pentagon-led operation in Cuba was quietly getting ready. Later, a U.S. military surveillance drone was seen flying close to Cuba.

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Asked about the Pentagon's plans for the Air Force On April 17, Trump told a reporter in a vague way, "Well, it depends on what your definition of military action is."