Trump’s Expansionist Dreams of Cuba Is a ‘Demolition Buy’

Mar 17, 2026 03:05 PM EDT, Tue

Cuba, to put it in real estate terms, is a demolition buy. You want the property, but the buildings are ramshackle. The only alternative is to tear down and rebuild.

  • The electric grid is kaput. It is off more than it is on. It is beyond bailing wire and duct repair.
  • The healthcare is in shambles with decaying buildings, insufficient medications and medical supplies.
  • The land is encumbered with property ownership from the pre-Communist period. Cuba took over private property as it’s a trait of Communism. Their constitution approved private ownership of property, so there are legal problems with who owns what.

Trump’s Cuba strategy is straightforward. The outcome will be anything but.

Trump seems confident he can do to Cuba what he did to Venezuela just over two months ago. He shouldn’t be.

Mar. 15, 2026, 6:00 AM EDT By Daniel R. DePetris

Even as the war in Iran remains in full swing, Trump is already eying his next target: Cuba.

Washington’s oldest adversary in the Western hemisphere is in the midst of an economic and social crisis the likes of which the Cuban Communist Party hasn’t confronted since the 1990s. That’s when the collapse of its former patron, the Soviet Union, forced the island to make do with a lot less. The Trump administration’s Cuba policy is only exacerbating those fissures.

The strategy is straightforward: place so much financial pressure on the Cuban government that it has no option but to meet Trump’s demands, like opening up the country to a multi-party democracy. Trump’s Jan. 29 executive order slapping any country that transports or exports fuel to Cuba with tariffs, combined with a new U.S. Justice Department initiative that seeks to indict senior Cuban officials, is meant to provide Trump with even more leverage in the ongoing talks with Havana.

If the White House is looking to emulate its success in Venezuela, it’s likely kicking on a locked door.

Trump seems confident he can do to Cuba what he did to Venezuela more than two months ago — decapitate the senior leadership, work with more pragmatic underlings and bring a former U.S. adversary into Washington’s orbit.

“As we achieve a historic transformation in Venezuela, we’re also looking forward to the great change that will soon be coming to Cuba,” Trump said at a White House event on March 7. His top diplomat in Cuba, Mike Hammer, even hinted there could be a Cuban-like equivalent to Delcy Rodríguez, who took over for former Venezuelan dictator Nicolás Maduro after his capture by U.S. forces in Caracas and is now cooperating with the Trump administration on everything from deportations to oil exports.

But if the White House is looking to emulate its success in Venezuela, it’s likely kicking on a locked door.

First, it should be noted that this is hardly the first time in U.S. history that an American president has tried to squeeze the island into submission. From the moment Fidel Castro ousted the U.S.-backed regime of Fulgencio Batista in 1959, the U.S. has sought to overthrow the Cuban Communist Party in its entirety or at least weaken it to the point where a negotiated transition to democracy is possible. John F. Kennedy instituted a comprehensive trade embargo on the island and approved the infamous Bay of Pigs operation to oust Castro. Lyndon Johnson green-lit sabotage operations against Cuba. Jimmy Carter sought to negotiate with Castro, only to pull out of talks. George W. Bush increased travel restrictions to the island and strengthened U.S. support for anti-regime opponents. Trump, meanwhile, overturned Barack Obama’s diplomatic normalization and replaced it with caps on remittances and more financial sanctions.

None of those efforts worked to change the Cuban regime from within, let alone topple it. Fidel Castro, Raul Castro and now Miguel Díaz-Canel have all used the U.S. embargo and subsequent pressure tactics as a convenient excuse to explain away their own failed economic policies. The only people who have been negatively impacted by U.S. policy over the last six decades are the Cuban people themselves, whose lives are a constant struggle for basic necessities and who are effectively penalized for their own rulers’ incompetence. Is more of the same really going to bring different results?

Second, the Cuban Communist Party is more unified and durable than Maduro’s regime ever was, which means attempts by the Trump administration to crack it by searching for a more pliable successor will prove more difficult. While Maduro fancied himself as Venezuela’s decisive autocrat, the fact is his position depended on the ability to manage multiple factions and personalities within the Venezuelan government, including Delcy Rodríguez, his interior minister, Diosdado Cabello and his defense minister, Vladimir Padrino López. Maduro did this in large part by allowing these figures to run their own fiefdoms and earn money through illegal activity. Venezuela’s government, in other words, was less a solid structure than a constellation of competing ministers, some of whom had different interests and prerogatives. One of those figures, Rodríguez, already showed that she was amenable to working with Washington economically when she negotiated with U.S. officials last year over Chevron’s access to Venezuelan oil fields.

Any dissent within the Cuban Communist Party or the Cuban military’s ranks is dealt with harshly, which deters officials in the bureaucracy from engaging in similar activity.

If there is a figure like this in Cuba, Cuba’s security services will know the answer. The regime might be awful at governance but it’s quite capable at snuffing out the smallest signs of discontent and disloyalty. There is no organized democratic opposition on the island, and those brave enough to protest on the streets are rapidly arrested, thrown in prison and in some cases sentenced for 30-year terms. Any dissent within the Cuban Communist Party or the Cuban military’s ranks is dealt with harshly, which deters officials in the bureaucracy from engaging in similar activity.

Cuba isn’t powerless to resist U.S. demands either. Unlike Venezuela, the island is only 90 miles off Florida, and if the regime’s back is against the wall, it will do what it can to complicate U.S. plans. Chief among the levers Havana can pull is irregular migration into the U.S. Some might view such a scheme as reckless or unlikely, but the regime has done it several times before.

The 1980 Mariel boat lift, which resulted in an influx of 125,000 Cubans to U.S. shores, was deliberately stoked by Fidel Castro at a time when U.S.-Cuba relations were at a low point. Fourteen years later, as Castro was getting frustrated with the Clinton administration and dealing with an economic collapse, Castro instigated yet another migration outflow (known as the “Balsero Crisis”), which eventually forced Washington to negotiate an immigration accord with Havana to stem the tide.

The Trump administration is currently in discrete talks with Cuba. Raul Guillermo Rodríguez Castro, Raul Castro’s grandson, is taking the lead on the Cuban side. Whether those negotiations succeed will be determined in part on whether Trump is willing to be realistic with his demands.

But if one of his goals happens to be a Cuban government doing his bidding, Trump is setting himself up for disappointment.

Daniel R. DePetris is a fellow at Defense Priorities and a syndicated foreign affairs columnist at the Chicago Tribune.

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