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Cuban Regime's Long History of Deception: Will Trump Be Next?

Wednesday, June 24, 2026 by Ethan Navarro

For over sixty years, the Cuban dictatorship has honed a survival tactic that has outlasted 13 U.S. presidents. This strategy involves making concessions, creating openings, and buying time until a change in leadership or a weakening of authority allows them to revert to their original stance. Carlos Sánchez Berzaín, a Bolivian lawyer and political scientist who also serves as the director of the Interamerican Institute for Democracy, elaborated on this in an interview with Tania Costa for CiberCuba.

"The Cuban dictatorship has mastered the art of manipulating space and time to ensure its indefinite survival. They've managed, deceived, and maneuvered their way through 13 U.S. presidencies, from Eisenhower to Biden, including Trump 45," Sánchez Berzaín stated.

The most extreme instance of this approach, according to the analyst, occurred with Barack Obama. He reestablished diplomatic relations with Havana, provided economic support via Pope Francis, and initiated a normalization process which, ten years later, the U.S. government itself deemed a "missed opportunity."

"And what did it achieve? Did it only allow the regime to steal more, commit more state terrorism, increase the number of political prisoners, and strengthen its criminal system? It served no other purpose," Sánchez Berzaín concluded.

Trump's Approach: A New Perspective on Cuba

Given this history, Sánchez Berzaín argues that the Trump 47 administration has a different perspective, recognizing Cuba as "the head of the snake."

"If Cuba hadn't existed as a dictatorship, Chávez wouldn't have had a regime to nurture. The entire criminal methodology of transforming Venezuela, Bolivia, Nicaragua, and Ecuador into dictatorships, as well as the erosion of sovereignty and international interventionism, is rooted in Cuban Castroist methodology," he explained.

For this reason, Sánchez Berzaín believes Washington cannot afford to let the Cuban regime survive. "They cannot let this dictatorship persist because it will eventually regenerate. It needs to be ended soon, within days or weeks. It's in a terminal state, and the United States is aware of this."

Concrete Actions Against the Cuban Regime

This pressure is reflected in tangible actions. Since January 2025, the Trump administration has imposed over 240 sanctions on Cuba, intercepted at least seven oil tankers—reducing crude imports by 80% to 90%—and compelled hotel chains like Meliá to exit 15 hotels on the island before the June 5 deadline.

The question of whether Trump might negotiate with the regime on migration—given the massive Cuban emigration and Washington’s aim to curb it—elicits a firm response from Sánchez Berzaín.

"The only agreement with the dictatorship is for it to leave. If the United States agrees to anything else, it's not an agreement, it's a deception. It's buying time at the expense of yielding space," he warns.

The analyst acknowledges that this pattern has repeated over 13 consecutive presidencies and expresses hope that it won't recur with the current administration. "Trump 47 will not join the gallery of U.S. presidents whom Cuba has manipulated as the fourteenth."

"This has happened under 13 presidents, and I hope it doesn't occur with Trump 47," Sánchez Berzaín concludes, leaving open the critical question of whether the dictatorship will once again manage to buy enough time to endure.

Understanding U.S.-Cuba Relations

How has the Cuban regime survived through multiple U.S. presidencies?

The Cuban regime has employed a strategy of making temporary concessions, creating openings, and buying time. This allows them to revert to their original stance once the political climate changes, enabling them to outlast various U.S. administrations.

What was the result of Obama's policy towards Cuba?

Obama's policy of reestablishing diplomatic relations and economic support was later viewed by the U.S. government as a "missed opportunity," as it did not result in significant positive change within Cuba.

Why does Sánchez Berzaín believe the Cuban regime must end?

Sánchez Berzaín argues that allowing the Cuban dictatorship to persist will enable it to regenerate and continue its influence, which has historically contributed to the establishment of other authoritarian regimes in Latin America.

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