Trump's maximum pressure strategy on Cuba: a repetition of historical failure or a real turning point?



Donald TrumpPhoto © The White House

Related videos:

The Republican senator Ted Cruz stated this Sunday that there is a greater likelihood than at any time in our lives of seeing new governments in Venezuela, Cuba, and Iran in the next six months.

Cruz's statements summarize the Trump administration's stance on Havana and reopen the debate on whether U.S. pressure can this time achieve what it has never succeeded in doing over 67 years of dictatorship.

Cruz's assertion is not empty rhetoric. It is based on a convergence of external pressure and internal implosion that distinguishes the current moment from all previous episodes of confrontation between Washington and Havana, from the Bay of Pigs in 1961 to the embargo, including the thaw during Obama's administration and the hardening of Trump's first term.

The strategy operates on three simultaneous vectors. The first was the capture of Nicolás Maduro by the Delta Force unit on January 3, 2026, which abruptly eliminated Venezuelan oil supplies of between 26,000 and 35,000 barrels per day, accounting for 80-90% of Cuba's oil imports.

The second, the Executive Order 14380, signed by Trump on January 29, which declared a national emergency and imposed tariffs on any country supplying crude oil to Cuba, forced Mexico to suspend shipments and the Coast Guard to intercept at least seven tankers. The New York Times described it as the first effective blockade since the Missile Crisis of 1962.

The third is Secretary of State Marco Rubio, who demands a complete change of the government system as a sine qua non condition for any normalization, anchoring himself in the Helms-Burton Act of 1996.

What structurally sets this episode apart from previous crises is the combination of internal collapse without an external safety net. The Cuban GDP has fallen by a cumulative 23% since 2019, with projections of an additional decline of 7.2% in 2026 according to The Economist Intelligence Unit. The effective population has dropped from 11.3 million to between 8.6 and 8.8 million due to mass exodus: over one million emigrants since 2021, equivalent to 10% of the population. The electrical system suffered at least two total collapses in March, with blackouts lasting up to 20-25 continuous hours in Havana and generation deficits exceeding 2,000 MW. Díaz-Canel even suggested cooking with firewood.

The historical pattern shows that whenever Cuba lost an external sponsor —the USSR in 1991, Venezuela partially in 2019— the regime sought new allies or made minimal concessions without yielding power. Today, Russia and China have symbolically reinforced their support: Putin promised to send oil, and the Russian Interior Minister visited Havana in January to advance surveillance technologies. However, a Russian tanker turned back due to warnings from Washington, highlighting the real limits of Moscow's support. For both powers, losing an intelligence node and a symbol of anti-Western resistance in the hemisphere would represent a significant strategic blow.

Díaz-Canel confirmed on March 25 that both he and Raúl Castro are participating in negotiations with representatives from Washington. Cuba released 51 political prisoners, compared to the 1,214 documented by Prisoners Defenders. The U.S. demands Díaz-Canel's resignation as a prerequisite for any agreement. The gap between both positions remains vast.

Cruz acknowledged the uncertainty of the moment: "I admit that there are a thousand ways this could go wrong. But this is what happens when you see the strength of United States." The question that history has yet to answer is whether that strength is enough this time to bend a dictatorship that has been resisting for almost seven decades.

Filed under:

CiberCuba Editorial Team

A team of journalists committed to reporting on Cuban current affairs and topics of global interest. At CiberCuba, we work to deliver truthful news and critical analysis.