In mid-July 2026, with over 240 sanctions imposed on the Cuban regime since January and an island that daily teeters on the brink of energy collapse, the question lingering in the Cuban community remains unanswered: why doesn’t Trump take the definitive step? Three experts debated this issue in a discussion hosted by Tania Costa on CiberCuba, reaching conclusions that range from strategic patience to frustration.
The starting point was the statement by the head of mission of the U.S. Embassy in Havana, Mike Hammer, who stated in February of this year in an interview with ABC in Spain, that "in 2026 we will see a historic change in Cuba" and that "the dictatorship will come to an end." Five months later, that promised change has not arrived, and there are doubts about whether it will come in the hoped-for manner.
For historian Omar Sixto we are not witnessing a change of heart from the U.S. "No, no, Trump has not changed his mind. In fact, even if it doesn't seem like it, there are many signs that indicate otherwise. The problem is that he doesn't take the step or press the button, but the signs are there. The issue is the hesitations, and we do not know for what reasons. There must be some."
The researcher from the Autonomous University of Mexico, Alejandro González Acosta provided a geopolitical explanation. “I wouldn’t want to be in President Trump’s shoes right now, because everyone is demanding—not only from Cuba, but from Ukraine, Iran, and so on—and he is just one person, and the United States is just one entity.”
To illustrate the complexity of expectations regarding Cuba, González Acosta referred to a historical image. "There is an old Cuban cartoon from the late 19th century that features Uncle Sam, and from the island, several Cubans appear, with one saying annexation, another saying non-intervention, another saying independence, and another saying Spanish autonomy, and the cartoon is titled 'What do Cubans want?' I believe that 100 years later, the situation is very similar."
For his part, historian Jorge León introduced a factor that, according to him, is often underestimated: the ego of the American president. "There is an element that is rarely taken into account, which is Trump's ego. He knows that solving the problem of Cuba will be a monumental achievement, one that will place him on a pedestal in history," he noted, adding that the American president "also has the historical knowledge of what Reagan accomplished, and he is on that path."
León also pointed out that the war with Iran has Trump "somewhat paralyzed" regarding Cuba, but suggested that the accumulated pressure might not require direct intervention. "All this negotiation revolves around an internal fracture, a collapse, an accumulation of factors with international pressure, which could bring down the tyranny without the United States needing to make a direct intervention."
Within Trump's own administration, there are differing opinions. Secretary of State Marco Rubio advocates for maximum pressure, although he expressed skepticism about the regime's willingness. "Honestly, I don't see much progress," he admitted.
Vice President JD Vance, for his part, revealed in June active diplomatic contacts between Washington and Havana to explore potential bilateral changes.
The backdrop is a devastated Cuba: blackouts lasting up to 25 hours and 30 consecutive hours, a projected contraction of GDP between -6.5% and -7.2%, and a reduction of between 80% and 90% in fuel imports. The midterm elections in November 2026 mark the political horizon that analysts identify as the opportunity for Trump to demonstrate results.
León, who declared in April that Cuba will experience a democratic transition in November, summarized the collective mood with a phrase: “I believe that silence can also be heard. I believe that yes, there are elements that are under the rug.”
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