Trump Says He’ll Send Marco Rubio to “Finish Up the Deal” in Cuba After Iran

Breaking

President Donald Trump said Friday, Oct. 23, that the United States will turn its attention to Cuba once the conflict with Iran is settled, and that Secretary of State Marco Rubio will be the man to close the deal. Asked about Cuba by an audience member at a rally at Florida Gulf Coast University’s Alico Arena in Fort Myers, Trump said, “Don’t worry. We’ll take care of Cuba on our way back from Iran. We’ll do a little stopover.”

Trump described U.S. warships returning from the Middle East and passing the island. “We’ll have one of them stop about 50 yards off the coast,” he said. “They’ll raise up their hands, and then we’re going to send Marco Rubio in to finish up the deal.” Trump then suggested even a stop might not be needed. “We don’t even have to stop,” he said. “We could just put him in there and he’ll figure it out. He’s a great guy.” During the roughly 90-minute speech, Trump also said more military action against Iran may still come, according to Reuters.

Details & Background

Rubio, the son of Cuban immigrants and a former U.S. senator from Florida, has led much of the administration’s Cuba policy. Later on Friday, he posted a message on X aimed at people inside Cuba. “To those who seek to create positive change in Cuba – now is the time,” Rubio wrote, urging them “to create the change you desire through a discrete partnership with the CIA.” The post did not elaborate, according to Reuters.

Pressure on Havana has been building all year. A U.S.-imposed oil blockade has left Cuba short of fuel, with frequent blackouts worsened by failing infrastructure, Reuters reported. In September, the administration announced new sanctions targeting Cuban elites and financial channels, and the State Department said Cuba’s government threatens U.S. national security. That same month at the United Nations General Assembly, Trump called Cuba a “failed state” and declared, “Freedom will be coming to Cuba,” prompting the Cuban delegation to walk out. The push follows the ouster of Venezuela’s leader earlier this year.

Reactions

Florida Republicans welcomed the message. Rep. Carlos Gimenez, R-Fla., who was born in Cuba, praised Rubio’s post, saying, “President Trump is serious about taking decisive action.” Trump encouraged the crowd to chant Rubio’s first name after laying out the scenario, according to RedState. Cuban Americans are an influential voting bloc in Florida, and Trump won 68% of their votes in the state in 2024, according to Reuters.

Critics took a very different view. United Nations human rights experts have condemned the oil blockade as a violation of international law, and rights advocates have described the administration’s threats as an “imperialist approach,” Reuters reported. Reuters’ report did not include a response from the Cuban government to Trump’s remarks or Rubio’s post.

Why This Matters to You

Cuba sits roughly 90 miles from Key West, and for more than six decades its communist government has been a source of instability in the hemisphere, from waves of migration to its partnerships with America’s adversaries. Any change in Havana would directly affect border security, the flow of migrants toward Florida and the safety of the region.

The rally was held to support Rep. Byron Donalds, the Republican nominee for Florida governor, but the message reached far beyond the state. For the many Cuban American families who fled the regime, Trump and Rubio are signaling that the administration intends to see real change on the island. Rubio’s direct appeal to Cubans makes clear the administration views this moment as an opening, not a stalemate. The coming months will show whether that pressure produces a free Cuba.