US imposed 2-week deadline during secret Cuba meeting

WASHINGTON − The United States has given Cuba a two-week deadline to release high-profile political prisoners as a gesture of good faith as part of the Trump administration’s broader demands for economic and political reforms on the island.

The demand was presented during a secret meeting April 10 in Cuba, according to a source familiar with the discussion.

Some of the names floated for release included Luis Manuel Otero Alcántara and Maykel Osorbo, dissident artists from the San Isidro movement who were sentenced in 2022.

In a statement to USA TODAY, a State Department spokesperson said the Trump administration remains committed to the release of 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 underway. 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 a U.S. government plane had landed in Cuba since 2016. Axios was the first news outlet to report the meetings took place.

The officials told the Cuban government that the island's economy is in free fall and that its ruling elites had a narrow window to make changes before circumstances irreversibly worsen, the State Department official said. The person said 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 United States proposed bringing Starlink's high-speed internet services to Cuba. But the officials said Havana needs to enact changes 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.

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 Washington and Havana for weeks as Trump warned a hostile takeover was possible. After capturing Venezuela's leader in January, the Trump administration tightened long-standing sanctions and oil shipments to Cuba as part of a broader campaign to force sweeping political changes on the Communist-run island. The country is already mired in a severe economic crisis, and the near-total blockade is pushing it toward collapse.

In recent weeks, Trump has said he believed that he would have the "honor of taking Cuba" and that the United States "may stop by Cuba" after it finishes with Iran.

The United States has signaled in recent days that Trump is still weighing his options. USA TODAY reported April 15 that military planning for a possible Pentagon-led operation in Cuba was quietly ramping up in case Trump gives the order to intervene. A U.S. military surveillance drone was later spotted flying near Cuba.

Asked about the Pentagon planning on Air Force One on April 17, Trump cryptically told a reporter: "Well, it depends on what your definition of military action is."