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Why is Trump talking about action on Cuba and what could that look like?
2026-05-15 · via Home - CBSNews.com

By

Caitlin Yilek

Politics Reporter

Caitlin Yilek is a politics reporter at CBSNews.com, based in Washington, D.C. She previously worked for the Washington Examiner and The Hill, and was a member of the 2022 Paul Miller Washington Reporting Fellowship with the National Press Foundation.

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Washington — President Trump has continued to dangle the possibility of military action against Cuba, appearing to be emboldened by his administration's intervention in Venezuela. He suggested earlier this month that "on the way back from Iran," an aircraft carrier could "come in, stop about 100 yards offshore, and they'll say, 'thank you very much, we give up.'"

After the U.S. military captured Venezuelan President Nicolás Maduro in January, Mr. Trump warned that he had his sights set on Cuba. Secretary of State Marco Rubio, standing alongside Mr. Trump at a news conference about the raid on Jan. 3, said the regime should be "concerned." 

And since Iranian Supreme Leader Ali Khamenei was assassinated in U.S. strikes on Iran in February, Mr. Trump's rhetoric against Cuba has escalated. On March 16, Mr. Trump told reporters in the Oval Office that he believed he would have "the honor of taking Cuba." 

"Taking Cuba in some form, yeah," he said. "Taking Cuba. I mean, whether I free it, take it — I think I could do anything I want with it, if you want to know the truth."

"Cuba's going to be next," Mr. Trump said later that month. 

Rubio, the son of Cuban immigrants, has been more direct about the administration's possible goals in Cuba, testifying to Congress in January, "we would love to see the regime there change," and saying it would be of "great benefit" to the U.S. Weeks later, Rubio said Cuba has to "change dramatically." 

"I mean Cuba has an economy that doesn't work and a political and governmental system that can't fix it," Rubio said on March 17 in the Oval Office. "The people in charge, they don't know how to fix it. So, they have to get new people in charge." 

Rubio reiterated the need for economic reform and political reforms and predicted the administration would "have more news on that fairly soon," he said on Fox News. 

"You cannot fix their economy if you don't change the system of government," he said. 

For now, experts on the region view the threats of military action in Cuba as bluster, saying it would involve much more effort than in Venezuela because of the political structure. Forcing gradual economic change, along with the resignation of Cuban President Miguel Díaz-Canel, through the threat of economic collapse and other sanctions is a more likely scenario, they said. 

"I think there are a number of factions within the administration where some would be happy to do a deal with most of the existing Cuban government if it gave greater access to businesses, and particularly to Cuban Americans to come back and invest," Paul Hare, who served as the British ambassador to Cuba from 2001 to 2004, told CBS News. "The other faction, I think, is insisting on a complete regime change." 

The Trump administration has been trying to choke Cuba's economy by imposing an oil blockade that experts say has pushed the Communist-ruled island to its most dire state since the collapse of the Soviet Union, which heavily subsidized Cuba's economy. In mid-May, the energy minister said that Cuba has run out of fuel, largely as a result of the blockade.

Still, the U.S. and Cuba have been talking, and on Thursday, May 14, CIA Director John Ratcliffe traveled to Havana, Cuba, for a rare meeting with senior Cuban officials, an agency official told CBS News, using the visit to deliver a message that the U.S. was prepared to expand economic and security engagement with Cuba if Havana "makes fundamental changes."

The deputy foreign minister of Cuba, Carlos Fernández de Cossío, said in an interview in March with NBC News that his nation does not see U.S. military action as "probable," but their military is "prepared" for any U.S. aggression. Cossío added that regime change is "absolutely" off the table.

What regime change could look like is another question. 

Christopher Hernandez-Roy, a senior fellow and deputy director of the Americas Program at the Center for Strategic and International Studies, said "regime management" is the "only realistic option." 

"Regime change is probably harder to accomplish than in Venezuela. Regime management, I would also argue, is probably harder to accomplish than in Venezuela because you have a power structure that's been in place for almost 70 years and is expert at repression and expert at sniffing out dissent. So is there a pressure point at which certain elements in Cuba think that it's better to change course? I think it's possible. But is it as easy as it is in Venezuela? I don't think so. I think it's probably harder," he told CBS News. 

"A purely diplomatic solution that doesn't rest on any sort of coercion, I don't think is possible," he added. 

Raúl Castro handed the presidency to Díaz-Canel in 2018, marking the first time since 1959 that a Castro was not formally leading the country. But Díaz-Canel is widely considered a figurehead and the Castros still have considerable influence. 

"He's not the person that actually wields the power in the country, but it would be seen as a symbolic win by the United States," Hernandez-Roy said. 

It's also unclear who would step in to run the country. 

One scenario could be a Delcy Rodríguez figure who would lead the island "very much in concert with and under the pressure of the United States," according to Lawrence Gumbiner, a career diplomat who led the U.S. Embassy in Havana during Mr. Trump's first term. 

"The first steps would be economic openings," Gumbiner said of how the U.S. could exert pressure over a regime-aligned leader. "I think the clear message will be like it is with Ms. Rodriguez — that you will do as we say, or else." 

Gumbiner said the "or else" carries the threat of military action, although he believes such a threat is minimal, and potential indictments. The top federal prosecutor in Miami has been exploring potential charges against Communist Party leadership, including economic crimes, drugs, violent crimes and immigration-related violations. And CBS News first reported on May 14 that the Trump administration is taking steps to indict former leader Raúl Castro.

A more ambitious move would involve bringing in someone from outside the regime who would push for constitutional changes, Hare said.

Gumbiner said that Mr. Trump is less concerned about political change, instead seeing the nation as a big opportunity for U.S. businesses. 

"Whether it's shipping, whether it's transportation, whether it's tourism, whether it's construction, I think Trump sees Cuba as kind of virgin territory, where it's been been kind of dormant for six decades, and where the U.S. business community can come in and really dominate the scene," he said. 

Gumbiner said Rubio likely wants to see broader change in Cuba than Mr. Trump, but he added that "there are a number of reasons why that's going to be complicated." The former diplomat said an upheaval to the nation's political structure "would involve tremendous U.S. effort." 

"It's important to realize that Trump, he does not want to do nation building," he said. "Rebuilding Cuba would be a nation building exercise if you want to redo it in a democratic, pluralist model. Whereas, making economic changes piecemeal is easier." 

Facing increasing pressure from the Trump administration, the Cuban government announced that it would allow Cuban nationals living abroad to invest in companies on the island. It marked a notable shift for the country, which had heavily restricted residents from starting private businesses until recent years. 

In late March, the U.S. allowed a Russian oil tanker to reach Cuba. Mr. Trump indicated it was a humanitarian gesture. 

"They have to survive," he said. 

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