Trump aides, allies portray military force in Cuba as last resort

May 19, 2026, 5:07am EDT
Politics
A vintage car in Cuba
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The News

As the Trump administration ramps up economic and diplomatic pressure on Cuba, it’s also sending a signal: Military action may be possible, but only if the current approach fails outright.

President Donald Trump has lobbed threats at Cuba’s communist government for months, saying recently that the US would be “taking over almost immediately” on its “way back from Iran.” But even as he and advisers grow impatient with the Cuban government over its ties to China, Russia, and Iran, Trump is still struggling to resolve his war with Tehran — making another military entanglement more challenging to take on.

For the moment, the administration is hitting Cuba with new sanctions and expanding a blockade that has recently left the country with no oil or diesel, part of a broader bid to force its leaders to the table. The US has increased surveillance flights in recent months as CIA Director John Ratcliffe made an unannounced trip to Havana to speak with Cuban officials.

The latest pressure campaign includes a coming indictment — expected to be announced on Wednesday, to coincide with Cuba’s independence day — against Raúl Castro, Cuba’s 94-year-old former president, who still holds significant sway over its government.

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“I don’t think they’re going to have to” use the military, said Sen. Rick Scott, R-Fla., who’s been in touch with the White House about Cuba. But he added a Trumpian caveat: “I don’t think you take anything off the table.”

Trump has shown this year, by ordering the ouster of the Venezuelan president followed by his conflict with Iran, that he’s never willing to rule out using military force. That posture adds a healthy dose of doubt to the belief among some people close to him that he would prefer a diplomatic solution, as does Secretary of State Marco Rubio’s skepticism that Cuba can succeed under its current government.

Aides close to Trump are sending somewhat conflicting messages. One White House official indicated confidence that the current effort can pay off with steep concessions, if not outright regime change: “Cuba is asking for help, and we are going to talk,” this official said, while pointing to Trump’s recent comments that the US “will be there to help them out” once the current leaders “fall.”

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Yet another US official pointed to grounds for so-called kinetic action if Trump chooses to take it. Asked about next steps should the administration tire of trying to negotiate, this official emphasized that Cuba remains on the list of state sponsors of terrorism — a designation the Trump administration reapplied after the Biden administration removed Cuba from the list — that could be used to justify further actions, military or otherwise.

“Clearly the main instrument of coercion that the Trump administration is using is economic,” said William LeoGrande, a professor of government at American University. “But there’s certainly the threat of military action in the background. They keep hinting at it.”

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Top Republicans have downplayed the possibility of military action in Cuba. Speaker Mike Johnson told reporters in March there wasn’t an “appetite” for ground troops and that the country was in the process of changing regimes anyway. “If it happens there is a regime change, I don’t believe we need American troops there,” he said.

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And while Trump was emboldened by his success in Venezuela, where the US captured then-President Nicolás Maduro and is now working closely with the country’s interim leader, sustained military action in Cuba could prove tougher. LeoGrande suggested it would be “difficult” to achieve the administration’s goals with military force in part because — as the conflict with Iran is proving — it can be hard to “change a regime with an air war.”

Any prolonged conflict could also result in a humanitarian crisis, he suggested.

Unlike in Venezuela, it’s also unclear whether there is any successor that the US could work with if it takes out top leadership in Cuba. The Castro indictment still leaves a host of other officials who would not necessarily be amenable to a change in relations with Washington the way that Delcy Rodriguez has been in Venezuela.

Cuban President Miguel Díaz-Canel warned on Monday that a US military operation would result in a “bloodbath.”

Still, Trump is likely to get plaudits from South Florida Republicans, who represent areas with a substantial Cuban American population, for squeezing the island nation’s government. Some of those lawmakers are expected to attend the Wednesday unsealing of charges against Castro.

“It’s not coming fast enough to get rid of the Castro family in Cuba, they destroyed the island for 65 years,” said Rep. Maria Elvira Salazar, R-Fla., of the potential indictment. “Thanks to President Trump, Cubans will see freedom, liberty, democracy, and a free market economy. We could be Taiwan in 10 years.”

Although the charges haven’t yet been unveiled, reports suggest they will be connected to Castro’s alleged role in the 1996 downing of planes operated by an exile group.

“If it happens, certainly about time. [Castro] murdered three American citizens, an American resident. They were humanitarian flights,” said Rep. Carlos Giménez, R-Fla.

The issue is clearly very personal to Rubio, himself a Cuban American from South Florida.

“When you go back to even the first trip he did as secretary, it was in the Western Hemisphere,” said one Rubio ally. “If I’m him, like, this goes far beyond the current job he has. … He sees the regime there as a threat to the freedom of the people in Cuba, and also not something that helps American interests.”

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Room for Disagreement

Plenty of other signals point to military action against Cuba as on the minds of Trump’s advisers: Rubio was photographed meeting with the leader of US Southern Command in front of a map of Cuba, stoking speculation about plans for military action.

And as Axios reported this weekend, the administration has accused Cuba of planning to attack US bases and ships using drones — another potential pretext for force.

The Cuban Embassy in Washington did not return a request for comment.

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Shelby and Nick’s View

Trump is certainly viewing Cuba through a similar lens to Venezuela, but the prolonged war with Iran has taken a political toll that will affect his decision on whether to use force.

It’s also not totally clear yet whether the administration is seeking complete regime change or whether it would be comfortable with a more US-friendly posture from the Cuban government. Despite Trump’s occasional allergy to transparency, we expect to hear more about his objectives before any military move.

And as Iran rattles Hill Republicans, it’s important to remember how much risk — including that of potential refugees — would come from starting a conflict with a country that’s famously just 90 miles from Key West, Florida.

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Notable

  • Cuba’s top diplomat in the US told The Hill that the country was preparing for an invasion and was not budging on its red lines.
  • The US is said to be increasingly willing to use military action, Politico reported.

Burgess Everett contributed.

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