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Fortune | FORTUNE

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4 ways Trump is following the Venezuela playbook with Cuba, and one where he isn't | Fortune
Ben Finley, · 2026-05-23 · via Fortune | FORTUNE

The Trump administration’s strategy against Cuba is looking a lot like the playbook for Venezuela: An oil blockade, a growing U.S. military presence, federal charges and repeated threats of intervention.

But similar pressure campaigns do not equal similar results, experts say, even if President Donald Trump has often warned that “Cuba is next.”

“President Trump viewed the Venezuelan intervention as a fantastic success,” said Brian Finucane, a senior adviser with the International Crisis Group and a former State Department lawyer. “And he’s sought to replicate the Venezuela model elsewhere, including in Iran. But obviously, Cuba, like Iran, is a very different country than Venezuela.”

If the U.S. were to depose Cuba’s leadership, there is no obvious successor who would work with the Trump administration, Finucane said. That is unlike Venezuela, where the U.S. captured leader Nicolás Maduro in January and his second in command, Delcy Rodríguez, stepped in with U.S. approval and remains in power.

Cuban officials, who were not authorized to comment publicly and spoke on condition of anonymity, say “there is no Delcy in Cuba.”

The number of American forces in the Caribbean Sea now is also smaller and far less foreboding than the massive military buildup off Venezuela’s coast in the months ahead of Maduro’s ouster, Finucane said. Plus, an indictment against a 94-year-old former Cuban leader — Raúl Castro — is less impactful than charging Venezuela’s sitting president with drug trafficking and using that to justify his capture.

Here are some of the similarities and differences between the U.S. pressure campaigns against Venezuela and Cuba:

Trump has threatened military action

Like other conflicts, Trump began to lay the groundwork for U.S. intervention in Venezuela — and the possibility for Cuba — with escalating threats months before military action took place.

He has warned the leaders of the Caribbean countries to either get in line or face American might. Weeks before the audacious military operation that plucked Maduro from power, Trump stood with his top national security advisers in Florida and made what would be one of his last public threats to the autocratic leader.

“If he wants to do something, if he plays tough, it’ll be the last time he’ll ever be able to play tough,” Trump said in December. Just after Maduro was whisked to the U.S. to face trial, Trump shifted his focus to other countries in the region, namely Cuba, as being next on his list.

“Cuba is ready to fall. Cuba looks like it’s ready to fall. I don’t know if they’re going to hold out,” he told reporters on Jan. 5.

He went on to threaten tariffs on any country that sells or supplies oil to Cuba and said the U.S. might have “the honor of taking Cuba” following military operations in Venezuela and Iran.

On Thursday, he repeated his threats, calling Cuba “a failed country.”

“Other presidents have looked at this for 50, 60 years, doing something,” Trump said. “And, it looks like I’ll be the one that does it.”

US squeezes countries with oil embargoes

U.S. oil embargoes on Cuba and Venezuela have been designed to have the same impact: Putting intense pressure on ruling elites — but push diametrically opposite means to achieve those goals.

With Venezuela, the Trump administration was targeting the country’s oil exports, aiming to starve the Maduro government of revenue. After Maduro’s ouster, the focus shifted to denying Venezuela the ability to export oil to certain countries — primarily Cuba, from which it did not receive cash payments — and forcing it to agree to U.S. conditions for such shipments.

Much of Venezuela’s crude is now or will soon be sent through U.S. refineries.

With Cuba, the embargo is aimed at starving the energy-strapped country of oil imports, although the U.S. has allowed some limited shipments to arrive on the island, which recently declared it had run out of reserves. The oil embargo, an extension of the broader U.S. blockade on Cuba in place for decades, has made it far more difficult for the government to provide electricity and gasoline to its citizens.

The measures could go too far, Finucane said, and prompt many Cubans to head 90 miles north for Florida in makeshift boats as many did in the 1990s.

“President Trump especially cares about immigration. And if they push too hard on Cuba and destabilize the island, there’s the possibility of some kind of a refugee crisis,” he said.

US brings charges against figures in power

The Justice Department had charged Maduro with narco-terrorism conspiracy and other counts during Trump’s first term in 2020.

The case was used to justify capturing Maduro, who is now in New York awaiting trial and has pleaded not guilty. The move changed Venezuela’s relationship with the United States, which has allowed the sale of previously sanctioned Venezuelan oil to U.S. companies and on global markets, a massive shift after largely blocking dealings with Venezuela’s government and its oil sector for years.

The immediate aim of the indictment against Castro over the 1996 shootdown of civilian planes flown by Miami-based exiles is to take another step up the ladder of escalation in the Trump administration’s pressure campaign, said William LeoGrande, a professor specializing in Latin American politics at American University in Washington.

But he said that capturing Castro following charges that include murder and destruction of an airplane would not change the operations of the Cuban government.

Castro “still has influence and the leadership seeks his opinion on major decisions, but he is not running the government on a day-to-day basis,” LeoGrande said.

Building up a US military footprint in the region

In the months before Maduro was captured, the U.S. dispatched a fleet of warships to the waters near Venezuela in what became its largest military buildup in Latin America in generations.

The nation’s most advanced warship, the USS Gerald R. Ford aircraft carrier, was notably rerouted from Europe to join in the operation. Three amphibious assault ships carried around 2,000 Marines as well as helicopters and Osprey aircraft.

U.S. forces spent months attacking small boats accused of smuggling drugs in the Caribbean and eastern Pacific Ocean — and still are carrying out those strikes — while fighter jets flew over the Gulf of Venezuela.

The actual mission to capture Maduro involved more than 150 aircraft launched across the Western Hemisphere.

The U.S. military now has a smaller force in the Caribbean Sea, which still includes two amphibious assault ships with Marines onboard. It touted the arrival of the USS Nimitz aircraft carrier and accompanying warships on the same day the charges against Castro were announced this week.

But the Nimitz is on its last ever tour, taking part in maritime exercises in the region, before being decommissioned.

“They’re very different situations, and it’s very difficult to see similar outcomes,” Finucane said. “A snatch-and-grab raid against Raúl Castro or someone who’s actually in a leadership position doesn’t seem like it’s going to have the same outcome in Cuba as in Venezuela.”

___

Associated Press writer Andrea Rodríguez in Havana contributed to this report.