The Trump administration has been dancing around the question of whether it will carry out military strikes against Cuba. I am told it is increasingly willing to take such a step.
That’s a significant escalation from a few months ago, when officials were primarily focused on using economic and diplomatic pressure to squeeze the communist regime in Havana.
A U.S. official and a person familiar with the administration’s discussions on Cuba told me that President Donald Trump and his aides have grown frustrated that the U.S. pressure campaign, which includes starving the island of fuel, has not led Cuba’s leaders to agree to significant economic and political reforms. So they’re taking the military option more seriously than previously.
“The mood has definitely changed,” said the person familiar with discussions, whom, like others, I granted anonymity to discuss a sensitive issue. “The initial idea on Cuba was that the leadership was weak and that the combination of stepped-up sanctions enforcement, really an oil blockade, and clear U.S. military wins in Venezuela and Iran would scare the Cubans into making a deal. Now Iran has gone sideways, and the Cubans are proving much tougher than originally thought. So now military action is on the table in a way that it wasn’t before.”
Last week, news broke that the U.S. is moving toward indicting former Cuban President Raul Castro, the 94-year-old brother of late Cuban dictator Fidel Castro. This has led to some speculation that the U.S. could carry out a military extraction operation against Castro, the same way it did against Venezuelan leader Nicolas Maduro in January.
But U.S. military planners are weighing an array of options beyond grabbing one or two individuals, I’m told. The military action could range from a single airstrike meant to scare the regime into concessions to a ground invasion meant to uproot it.
U.S. Southern Command has in the past few weeks “convened a planning series” — in other words, started drafting plans for potential military action — the U.S. official and the person familiar with the talks told me.
No action is imminent. The Pentagon has plenty of firepower in the region. Cuba, a nation of 10 million, is just 90 miles off Florida’s coast.
One highly unlikely scenario is the use of Cuban exiles in any mission. “They have determined that the exiles have no role here except as cheerleaders and gadflies. This won’t be Bay of Pigs 2.0,” the person said.
A White House official reiterated to me Trump’s claims that Cuba will soon “fall” and “we will be there to help them out.” The official added: “It’s the job of the Pentagon to make preparations in order to give the commander-in-chief maximum optionality. It does not mean the president has made a decision.”
Administration officials already are laying the public relations groundwork for military moves.
Secretary of State Marco Rubio hinted at something ominous in an interview with Fox News last week. “We’ll give them a chance,” said Rubio, who also serves as national security adviser. “But I don’t think it’s going to happen. I don’t think we’re going to be able to change the trajectory of Cuba as long as these people are in charge.”
Over the weekend, Axios reported that Cuba had acquired hundreds of military drones and had discussed ways to use them in case hostilities erupt between Washington and Havana. Many national security analysts took that report to be a leak aimed at making a case for a U.S. military strike on Cuba.
The Cuban Embassy in Washington did not reply to my requests for comment.
It’s always unwise to predict what the capricious Trump will do, so maybe don’t rush to Kalshi just yet.
Trump also has to consider the politics given his sinking poll ratings as gas prices leap due to the Iran war. The size of a Cuba operation, if there is one, could come down to what he feels his MAGA backers will tolerate.
“They could try to do a pretty small operation, but if that’s what they’re thinking they may be overestimating again what they could accomplish,” said Brian Latell, a former senior CIA official who dealt with Cuba.
But there’s no question the administration’s position on Cuba has grown increasingly harsh, especially in the last few weeks, and I hear from people close to the administration and in it that the U.S. maneuvering, including targeted media leaks, is due to sincere exasperation with the Cuban leadership.
Cuban officials don’t seem to fully grasp how economically dysfunctional their country has become, the U.S. official said. They respond to U.S. pressure by offering ideas such as allowing outside investment in hotels when their real problems are structural, including with their dilapidated power grid.
It’s also not always clear who is truly in charge in Havana or how much power the Castro family retains, the official added.
“The system is so calcified and consensus-based. They are living in another reality, and they literally do not care about the Cuban people at all,” the U.S. official said.
Cuban officials have been asking Russia for more help, the U.S. official said. Moscow already sent one tanker of fuel that the U.S. allowed to reach the island in late March, offering a temporary reprieve.
Cuban President Miguel Díaz-Canel wrote on X on Monday that U.S. military aggression against Cuba “would provoke a bloodbath of incalculable consequences.”
He appeared to be responding to a rash of recent actions that have made the Trump administration’s impatience increasingly obvious.
Aside from the report about the drones and the potential Raul Castro indictment, they include: an expansion of U.S. sanctions against Cuba; the publicizing of CIA Director John Ratcliffe’s visit to the island last week, during which he made several demands of Havana; reports that the U.S. is increasing surveillance flights over the island; and the U.S. and Cuba sparring over conditions attached to a U.S. offer of $100 million in aid.
Defense Department officials did not reply to my requests for comment, but a State Department spokesperson repeated administration allegations that Cuba is a haven for terrorists and U.S. adversaries.
Rubio’s public messaging has shifted as the administration’s internal calculus has changed.
Rubio is a U.S.-born child of Cuban immigrants and he has long loathed the oppressive, corrupt Havana regime. But in the initial days after the Venezuela operation, which led to the cutoff of Venezuelan oil exports to Cuba, Rubio emphasized the importance of economic change in Cuba more than political change.
Such messaging suggested that, at the time, Rubio wanted to move deliberately and methodically in Cuba — to limit the chaos of a potential sudden political collapse. (Or perhaps this is what Trump wanted, and Rubio went along with it; spokespeople for the administration would not tell me either way.)
The idea was to convince the existing Cuban leadership to make serious economic reforms. Such reforms include privatizing many state assets; giving Cuban citizens more internet access; and allowing more foreign investment.
But, according to people familiar with the discussions, the regime saw such moves as threats to its survival. The regime’s view — and it’s not entirely unfounded — is that many of Cuba’s economic problems are due to the decades-old U.S. embargo on the Caribbean country and other U.S. pressure. There’s also certainly precedent for the idea that allowing economic change could undermine an authoritarian’s power.
As the months went on, Rubio’s message changed. He began to stress political change alongside economic change. More recently, he’s spoken of the need to toss out the “people in charge” without getting too specific.
I’m told that this isn’t a political move to appease Cuban-American activists in his home state of Florida. Rather, Rubio has become increasingly convinced that the regime in Havana is incorrigible.
Perhaps most intriguingly in recent weeks, Rubio has played up the idea that Cuba poses a national security threat to the U.S. — allegations backed up with suggestive photos from Southcom.
This is a message echoed by others in the administration, who say Havana’s links to Moscow and Beijing make it a special danger and note that Cuba is listed on the U.S. list of state sponsors of terrorism. (Plenty of analysts say the notion of a Cuban threat to the U.S. is wildly overstated).
According to a CIA official who shared background information about Ratclife’s recent visit, the spy chief “made clear that Cuba can no longer serve as a platform for adversaries to advance hostile agendas in our hemisphere.”
What I would warn Cuba watchers against is believing that Trump’s struggles in Iran will hold him back from carrying out a military operation against Cuba.
The mess in Iran could leave the president impatient to score another win. He may see Cuba as an easy victory.
That could prove a miscalculation, former U.S. officials and analysts warned. “There are true believers there,” a former State Department official who dealt with Cuba said.
Of course it won’t be simple. It never is. But that rarely stops Trump.