What Does the Trump Administration Want With Cuba?

Feb 20, 2026

Andrés Pertierra, historian on post‑1959 Cuban regime durability, offers on‑the‑ground views of Cuba’s economic and humanitarian collapse. Michael Bustamante, University of Miami chair in Cuban and Cuban American studies, links U.S. policy shifts to sanctions, remittances, and regional politics. They discuss the oil embargo, financial isolation, effects on private entrepreneurs, diaspora divisions, and wider regional fallout.

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INSIGHT

Oil Embargo Is The Immediate Pressure Point

The novel and most harmful policy is the U.S.-led oil embargo that deters suppliers by threatening punitive measures.
That embargo, plus Title III Helms-Burton effects, has immediate economic and transport fallout for Cuba.

INSIGHT

Financial Isolation Multiplies Sanctions' Impact

U.S. sanctions have extraterritorial effects because global banks avoid transactions tied to Cuba.
That financial isolation limits Cuba's ability to trade even with countries not bound by the U.S. embargo.

INSIGHT

Policy Flip-Flop Harms Investment And Reform

Post-Cold War engagement was seen as the rational policy, but domestic U.S. politics keeps reverting to pressure.
Flip-flopping U.S. policy creates uncertainty that deters investment and complicates Cuban private-sector growth.

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Cuba is spiraling into a humanitarian crisis. The country’s long-standing economic and political turmoil reached new heights this week as the effects of the Trump administration’s oil blockade took hold.

The president’s targeting of Cuba is part of the administration’s broader attacks on the region, where the U.S. kidnapped Venezuelan President Nicolás Maduro and his wife Cilia Flores earlier this year and has executed more than 140 people in boat strikes.

As the U.S. hurtles toward war with Iran and further military action in the Middle East and continues to fund Israel’s genocide in Gaza, Cuba is just the latest foreign policy arena where the Trump administration has further ensnared the U.S. This week on The Intercept Briefing, senior politics reporter Akela Lacy speaks with fellow reporter Jonah Valdez about how U.S. foreign policy is impacting the upcoming midterm elections and Valdez’s recent reporting on how a new anti-Zionist PAC has associated with influencers that have made statements that are outright antisemitic.

Lacy also speaks to University of Miami history professor Michael Bustamante and Andrés Pertierra, a historian of Cuba specializing in post-1959 regime durability, about the crisis unfolding in Cuba.

Missing from mainstream news coverage of Trump’s attacks on Cuba and U.S. efforts to impose regime change in the region is a recognition of how Trump’s policies fit into his attacks on immigrants in the U.S., Bustamante says.

“One of the, I think, subtext of why this administration might be keen on government change in Cuba, like in Venezuela, it's not just about being able to plant the flag and say, ‘We buried communism in the Americas. Something that no other president could do,’” Bustamante says.

“It's also about, we can deport more people. And we can deport more people. And so how does the Cuban American community react to that? That, I think, is an open question. Something that I haven't seen linked yet to the conversation about regime change, per se.”

The Trump administration’s strategy is likely to backfire, Pertierra says.

“You don't get long-term cooperation stability through fear,” he says. “So I don't think it's actually going to solidify the U.S. position in Latin America. I think it's going to further weaken it.”

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