The Trump administration has been playing around with the question of whether to launch a military strike against Cuba. I am told that it is getting ready to take that step.
That’s a sharp increase from the past few months, when officials focused primarily on using economic and diplomatic pressure to clamp down on the communist regime in Havana.
A US official and a person familiar with the government’s discussions on Cuba told me that President Donald Trump and his aides are frustrated that the US pressure campaign, which includes starving the island of oil, has not made Cuban leaders agree to major economic and political reforms. So they are taking the military option more seriously than ever before.
“The situation has definitely changed,” said a person familiar with the conversation, who, like others, I did not name to discuss a sensitive issue. “The initial thinking about Cuba was that the leadership was weak and that a combination of increased sanctions enforcement, the oil embargo, and US military victories in Venezuela and Iran would scare the Cubans into making a deal. Now Iran has stepped aside, and the Cubans seem tougher than previously thought. So now military action is on the table in a way that wasn’t the case.”
last week,the news brokethat the United States is moving to indict former Cuban President Raul Castro, the 94-year-old brother of the late Cuban dictator Fidel Castro. This has led to speculation that the United States may launch a military operation against Castro, as it did against Venezuelan leader Nicolas Maduro in January.
But US military planners are weighing a range of options beyond grabbing one or two people, I’m told. The military action could start with a single air strike intended to intimidate the government into accepting a ground invasion intended to oust it.
The U.S. Southern Command has in the past few weeks “summoned a series of planning” — in other words, begun preparing plans for possible military action — a U.S. official and a person familiar with the talks told me.
No action is imminent. The Pentagon has plenty of firepower in the area. Cuba, a nation of 10 million people, is located just 90 miles off the coast of Florida.
One highly unlikely scenario is the use of Cuban exiles in any mission. “They have decided that the exiles have no role here except as cheerleaders and deaf people. This will not be Bay of Pigs 2.0,” the person said.
A White House official echoed Trump’s claim that Cuba would “fall” soon and “we will be there to help them.” The official added: “It’s the Pentagon’s job to make preparations to give the commander in chief the top choice. It doesn’t mean the president has made a decision.”
Administration officials are already laying the groundwork for public relations for military action.
Secretary of State Marco Rubio made an ominous point in theinterview with Fox Newslast week. “We’re going to give them a chance,” said Rubio, who also serves as national security adviser. “But I don’t think it will happen. I don’t think we will be able to change the direction of Cuba as long as these people are in power.”
Over the weekend, Axios reported that Cubathey had bought hundreds of military dronesand they had discussed ways to use them if hostilities broke out between Washington and Havana. Many national security analysts considered the report to be a leak aimed at making a case for a US military attack on Cuba.
The Cuban Embassy in Washington did not respond to my requests for comment.
It’s not always wise to predict what the brainless Trump will do, so maybe don’t rush Kalshi just yet.
Trump also has to focus on politics due to his sinking poll numbers as gas prices rise due to the Iran war. The scale of the Cuban operation, if it exists, may reach what he feels his MAGA supporters will tolerate.
“They may try to do a very small operation, but if that’s what they think they may be overestimating what they can accomplish,” said Brian Latell, a former senior CIA officer who dealt with Cuba.
But there’s no doubt that the administration’s stance on Cuba has become increasingly harsh, especially in the last few weeks, and I’m hearing from people close to the administration and within it that the American maneuvering, including the leaks to the media, is due to genuine anger with the Cuban leadership.
Cuban officials do not seem to fully understand how their country has fallen economically, the US official said. They are responding to US pressure by offering ideas such as allowing foreign investment in hotels when their real problems are structural, including a dilapidated electricity grid.
It’s also not always clear who leads Havana or how much power the Castro family retains, the official added.
“The system is calculated and based on consensus. They live in another reality, and they don’t really care about the Cuban people,” the US official said.
Cuban officials have been asking Russia for more help, the US official said. Moscow has already been sentone fuel tankwhich the United States allowed to reach the island at the end of March, providingtemporary relief.
Cuban President Miguel Díaz-Canelwrote on XMonday that a US military invasion of Cuba “will provoke bloodshed of incalculable consequences.”
He appeared to respond to the urgency of recent moves that have made the impatience of the Trump administration increasingly apparent.
In addition to reports about drones and the possible impeachment of Raul Castro, they include: athe expansion of US sanctionsagainst Cuba; announced by CIA Director JohnRatcliffe’s visitto the island last week, where he made several claims to Havana; notice that the United States isthe rise of observational aircrafton the island; and the US and Cuba squabbling over US termsoffer of 100 million dollarsin aid.
Defense Department officials did not respond to my requests for comment, but a State Department spokesman repeated the administration’s claim that Cuba is a haven for terrorists and enemies of the United States.
Rubio’s public messaging has changed as the administration’s internal calculations have changed.
Rubio is the American-born son of Cuban immigrants and has long resented Havana’s oppressive and corrupt regime. But in the early days after the Venezuelan operation, which led to the cutoff of Venezuelan oil exports to Cuba, Rubio emphasized the importance of economic change in Cuba over political change.
Such messages suggested that, at the time, Rubio wanted to move to Cuba deliberately and systematically – to reduce the chaos of a possible sudden political collapse. (Or maybe this is what Trump wanted, and Rubio went with it; administration spokespeople wouldn’t tell me either way.)
The idea was to convince the current Cuban leadership to make major economic reforms. The reforms include privatizing many government assets; giving Cuban citizens more access to the Internet; and allow more foreign investment.
But, according to people familiar with the discussions, the government saw such moves as threats to its existence. The government’s view – and it’s not entirely unfounded – is that many of Cuba’s economic problems stem from decades of US embargoes on the Caribbean country and other US pressures. There is alsocertainly an introduction to the ideathat allowing economic change can weaken authoritarian power.
As the months went by, Rubio’s message changed. He began to emphasize political change along with economic change. Recently, he has talked about the need to fire “the people in charge” without being specific.
I am told that this is not a political move to appease Cuban-American activists in his home state of Florida. Instead, Rubio is increasingly convinced that the government in Havana cannot be reformed.
Perhaps most interestingly in recent weeks, Rubio has played up the idea that Cuba bringsnational security threatfor the United States – claims supported byRecommend images from Southcom.
This is a message supported by others in the administration, who say Havana’s ties to Moscow and Beijing make it a special danger and note that Cuba is listed on the US list of countries that sponsor terrorism. (Many analysts say the concept of a Cuban threat to the United States is outdated).
According to a CIA official who shared background information on Ratclife’s recent visit, the intelligence chief “made it clear that Cuba can no longer be used as a platform for dissidents to advance hostile agendas in our world.”
I would caution Cuba watchers against believing that Trump’s struggle in Iran will prevent him from carrying out a military operation against Cuba.
Chaos in Iran could make the president impatient for another victory. He may see Cuba as an easy victory.
That could prove misleading, former US officials and analysts warned. “There are true believers there,” said a former State Department official who covered Cuba.
Of course it won’t be easy. It is never. But that rarely stops Trump.



