We Need To Talk About Cuba

The Trump administration really, really wants to foment regime change in Havana. I'm sure this will end well.

Photo by JF Martin on Unsplash

It has been a very busy 2026 in the world of international relations. And for most of this year, the hard-working staff here at Drezner’s World has had a Post-It note saying, “write something about Cuba.” That is because I am genuinely baffled by what the Trump administration thinks is going to happen.

You see, back in January the U.S. imposed an oil embargo on Cuba soon after the Trump administration successfully grabbed Venezuela’s Nicholas Maduro. With their Venezuelan energy lifeline eliminated, the Trump administration clearly believed that Cuba’s communist regime was on its last legs and close to collapsing. This seemed like a debatable proposition; after all, Cuba’s regime has weathered previous periods of extreme economic distress without collapsing. Still, coasting on the momentum from the Venezuela operation, the administration opted for a maximum pressure campaign against Cuba.

A few months later, in mid-March, Trump expressed confidence that a “friendly takeover” of Cuba was just a matter of time. A few days later in the Oval Office he told reporters:

I think Cuba sees the end. All my life I’ve been hearing about the United States and Cuba. When will the United States do it? I do believe I’ll be the honor of — having the honor of taking Cuba….. Whether I free it, take it — I think I can do anything I want with it, you want to know the truth. They’re a very weakened nation right now.

It’s worth pausing here for a moment to note how extraordinary it is that the United States has been able to impose this embargo without much in the way of negative blowback from the rest of the world. An embargo is an act of war, but no other country has raised much of a stink about U.S. actions in the Caribbean. That could be because there are a whole bunch of other U.S. actions that have raised hackles and Cuba is literally in America’s neighborhood.

More than two months after Trump’s statement, the administration’s policy towards Cuba reminds me of a strategy that Jason Mendoza frequently advocated for in The Good Place:

The Trump administration might be floundering in the Persian Gulf, but it seems perfectly willing to throw a Molotov cocktail in the Caribbean. The indictment of former Cuban leader Raúl Castro last week certainly adds to the U.S. coercive pressure.

Would forcible U.S. regime change work? No doubt, the communist Cuban regime has long a distinguished history of repressing its citizenry and running the Cuban economy into ground. Peaceful regime change is a delicate, intricate task — but it would benefit both American foreign policy and the Cuban people in the long run.

And Cuba is definitely suffering right now. Earlier this month Cuba’s energy minister said the island nation had run out of diesel and fuel oil, triggering protests in Havana. According to the New York Times’ Ed Augustin and Lisette Poole González, the embargo, combined with the Cuban government’s longtime mismanagement of its economy, is imposing severe hardships across the island:

Today, some people can’t even afford charcoal, and resort to chopping firewood to cook in their homes.

Life here and across much of Cuba, already difficult because of an economy that has been in shambles for years, has become even worse since the Trump administration mounted its escalating pressure campaign against the country’s communist government….

The Cuban government says its oil reserves have run out and that its aging electric grid is becoming increasingly unreliable. The country produces some oil but far from enough to meet its needs.

Outside Havana, the capital, power outages now last 20 hours a day. The lack of energy has set off an enormous humanitarian crisis that has become deadly….

Residents are sleep-deprived. Because nobody knows when the power will come on, people leave lights and fans on. If the electricity kicks on, the sudden glare or cool breeze will wake them so they can do their chores before another outage.

So this seems like a fair amount of economic and mental distress.

At the same time, Cuba’s ability to defend itself against a U.S. attack also seems to be compromised. The Wall Street Journal’s José de Córdoba and Ian Lovett report that Cuba’s military — which was a formidable fighting force back in the days of Red Dawn the Cold War, is now a husk of its former self:

Cuba’s armed forces once fielded tens of thousands of well-trained soldiers during the height of the Cold War, deploying to conflicts from Angola to Syria.

Today, as the U.S. sends an aircraft carrier to the Caribbean in a pressure campaign to change the island’s Communist government, Cuba’s military is a ghost of its former self.

Until the decline and fall of its benefactor, the Soviet Union, Cuba had an army of more than 200,000 soldiers. Now that force is down to some 40,000 to 45,000 active-duty soldiers divided in three parts to defend the country’s east, west and center….

Morale and motivation also are factors. Cuba’s military has been living through a yearslong economic crisis that has exhausted the population. And those troops have been unable to train or maintain their weapons, said Craig Deare, who served early in Trump’s first administration as senior director for Western Hemisphere affairs at the National Security Council.

“Maybe their rifles work and maybe they have bullets,” Deare said. “But when you’re going against the best in the world, you don’t have a chance.”

There is no indication that Cuba has any offensive capability, but it could fight a war for survival in the event of a U.S. invasion, said Evan Ellis, professor of Latin American studies at the U.S. Army War College.

“It would come down to how long they could hold out with guerrilla tactics,” Ellis said. “The core strategy of the Cuban Communist Party is survival.”

Ironically, the Trump administration has been busy hyping up the potency of the Cuban threat in order to justify the embargo and, quite possibly, an invasion. U.S. officials accuse Cuba of housing Russian and Chinese eavesdropping posts (likely true) and leaked to Axios that they might pose a drone threat to the U.S. mainland (likely BS). The point is that Cuba is not a serious national security threat but the Trump administration needs to claim it is in order to justify its actions.

The Cuban regime’s survival mode seems to be flummoxing Trump and his advisors. Negotiations have been ongoing, but as Politico’s Nahal Toosi explains, Trump is still not getting what he wants:

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.”….

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….

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.

Much as I would love to see democratic regime change come to Cuba, I have absolutely zero faith in this administration to pull off anything resembling “forcible and democratic regime change.” That the Trump administration does not comprehend what the current Cuban government is doing is certainly one tell. One would have hoped that the Iran fiasco would have injected some humility into the current administration, but no dice.

As Politico’s Toosi and Daniel Desrochers explain, any regime change in Cuba would necessitate a massive amount of public investment into Cuban infrastructure and social support — and the likelihood of private sector buy-in would be low:

“You’re talking about a country that absolutely, 100 percent needs to be redone,” said Horacio Garcia Jr., a Cuban-American business leader based in Miami who is involved with the Cuban Liberty Council, which pushes for democracy in Cuba. “There’s no infrastructure for anything, for water, electricity, nothing, nothing. There’s not really a fair banking system. Everything needs to be done from the ground up. You’re talking about a country that’s in ruins.”

Unlike Venezuela, whose oil sector is the main economic driver, there is no single, dominant industry for Trump to tap in Cuba….

And the long reign of Havana’s communist regime has led to a far more atrophied private sector, as well as decaying public utilities. Any effort to open Cuba comes with the heavy burden of history, ranging from an expatriate community looking to recoup seized property to layers of U.S. policy that would need to be unwound to promote business development.

That includes unraveling decades of U.S. sanctions, a process that would likely need some approvals from Congress….

“Cuba is a complex, nuanced place,” said Mark Entwistle, the former Canadian ambassador to Cuba. “So every aspect of it has whole backstories to it and rabbit holes all over the place.”

A Trump administration move on Cuba would likely be less successful than the Venezuela operation and would likely spur a wave of migration into the United States — a cruel irony given this administration’s attitude about migrants.

Consider this column something of a marker. The Trump administration is intent on either coercing or forcing the end of the current Cuban regime. No doubt Trump wants to do this because a communist Cuba has bedeviled U.S. presidents for the last 65 years — and he could slice this Gordian knot when no president before him did so.

The thing is, this administration’s track record is so utterly abysmal that it is impossible to expect forcible regime change in Cuba to end well. It is unlikely that Trump officials have game-planned this out in any detail. And I am left wondering just how much more foreign policy chaos this president will unleash while he occupied his office.

Hopefully I’m wrong. But I don’t think I am.