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4 ways Trump is following the Venezuela playbook with Cuba, and one where he isn’t
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4 ways Trump is following the Venezuela playbook with Cuba, and one where he isn’t

Fortune · May 23, 2026, 3:00 PM · Also reported by 2 other sources

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

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