March 27, 2026
Will U.S. pressure lead to regime collapse in Cuba?
While the international community’s attention is focused on the Iran war, the Trump administration has ratcheted up pressure on Cuba’s communist regime in a bid to install leadership it believes would better align with U.S. interests.
In this DEFP Q&A, Fellow Dan DePetris evaluates whether a Venezuela-style approach to Cuba could advance U.S. interests and what a more effective U.S. policy toward Cuba would look like. (This interview has been lightly edited for clarity.)
What is the state of play regarding the U.S. pressure campaign on Cuba?
DePetris: The Trump administration has spent the last several months enacting a significant pressure campaign on the island, and they’ve done this mainly through economic coercion. The U.S. has essentially decided to place a de facto oil embargo on Cuba to make it more difficult for third parties, whether it be Mexico or Venezuela, to send oil to the country.
The administration has also cracked down very hard on Cuba’s doctor program. Cuba exports many of its healthcare professionals worldwide. There are about 40,000 to 50,000 Cuban doctors working in other countries, generating about $4 billion in annual revenue, which is not insignificant for a country like Cuba.
By cracking down on these programs, the administration is trying to starve the Cuban government into coming to the table with the United States in a weakened position.
Is a Venezuela-style approach in Cuba likely to work?
DePetris: Essentially, what the administration did in Venezuela was to take out Nicolás Maduro, who was the president at the top of the Venezuelan political system, and throw the dice with his deputy, Delcy Rodriguez. She is proving to be far more pragmatic and willing to cooperate with the United States on things like oil access and kicking out Cuban intelligence operatives that had operated on Venezuelan soil for decades.
I think the administration is ultimately trying to recreate that in Cuba. But the Cuban regime does not operate as the Venezuelan regime did under Maduro. In Venezuela, you had competing factions within an overarching system, and Maduro was really a power broker balancing competing priorities. In Cuba, you have a much more top-down system that has developed over the past six decades. The political systems of the two countries are not identical; I would argue they are not even similar.
So the administration’s bid to replay the Venezuela playbook inside Cuba will be tougher to execute because the regime in Havana knows how to survive. It’s going to be very hard to divide them from within. We’ll see if the plan works—I’m betting it doesn’t.
What would a better Cuba policy look like?
DePetris: The policy that Trump is enacting now is completely unneeded and unnecessary. There’s been a perception within the U.S. body politic, ever since Fidel Castro rose to power in 1959, that Cuba is a direct, dire security threat to the United States.
Cuba undermined U.S. foreign policy not only in the Western Hemisphere but also in places like Africa, the Middle East, and parts of Asia. That view was very prominent during the Cold War and, in some ways, understandable. Cuba is a small country, but it punched above its weight. You can’t make that argument today though. The Cuban economy is just a disaster, and that’s probably putting it charitably. The Cuban military is a shell of what it was 30 to 40 years ago.
The notion that Cuba presents some sort of imminent threat to the United States no longer passes the laugh test. What I have been arguing is that all the United States really needs to do is to normalize relations with Cuba. It’s an argument that’s been made repeatedly over the last 20 years. But for some reason—whether it’s domestic U.S. politics or it’s just a completely inaccurate perception of the threat Cuba poses to the United States and the Western Hemisphere—that very simple policy has been undermined.
The one exception was when the Obama administration negotiated with Cuba and granted sanctions exemptions and temporary waivers on certain banking activities, among other things. The embargo was still on the books, but it was not enforced to the fullest extent.
Besides that brief period, Cuba policy has essentially looked the same over the last 60 years. You could draw a straight line from the 2026 policy to what it was in 1961, when the trade embargo was first enacted. The United States should normalize relations with Cuba. It doesn’t have to worry about it as some sort of security threat.
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