Why Hasn't Trump Pushed the Button on Cuba? Historians Weigh In

In mid-July 2026, despite imposing over 240 sanctions on the Cuban regime since January and facing an island teetering on the brink of an energy collapse, the Cuban community remains puzzled: Why hasn't Trump taken decisive action? This question was the focus of a discussion hosted by Tania Costa on CiberCuba, where three experts offered insights ranging from strategic patience to outright frustration.

The conversation began with a statement from Mike Hammer, the head of the U.S. mission in Havana. In a February interview with Spain's ABC newspaper, Hammer predicted, "2026 will witness a historic change in Cuba," and confidently declared, "the dictatorship will end." Yet, five months on, this anticipated transformation has not materialized, leaving many skeptical of its promised arrival.

Omar Sixto, a historian, dismissed the notion of second thoughts from the U.S. "No, no, Trump hasn't had a change of heart. In fact, despite appearances, there are numerous signs that the intention is there. The issue lies in the hesitation to take action, for reasons we don't fully understand. There must be some underlying cause," he speculated.

Geopolitical Challenges and Historical Parallels

Alejandro González Acosta, from Mexico's National Autonomous University, provided a geopolitical perspective. "I wouldn't want to be in President Trump's shoes right now, as demands are coming not just from Cuba, but also from Ukraine, Iran, among others, and he is but one man, and the United States is but one nation," he remarked.

To highlight the complex expectations surrounding Cuba, González Acosta invoked a historical cartoon from the late 19th century. The illustration depicted Uncle Sam surrounded by Cubans with conflicting aspirations—annexation, non-intervention, independence, and Spanish autonomy—and was aptly titled "What Do the Cubans Want?" He noted, "I believe the situation remains much the same, even after a century."

The Role of Trump's Ego and International Pressure

Meanwhile, historian Jorge León introduced an often-overlooked factor: the ego of the American president. "There's an element that is seldom considered, which is Trump's ego. He understands that resolving the Cuban issue would be a monumental achievement, placing him prominently in history," León observed, drawing parallels to the accomplishments of Reagan.

León also pointed out that the ongoing conflict with Iran has left Trump "somewhat paralyzed" concerning Cuba. However, he suggested that accumulated pressures might ultimately lead to significant change without direct U.S. intervention. "The entire negotiation revolves around an internal fracture, a collapse, and a buildup of international pressure that could topple the tyranny," he stated.

Within Trump’s administration, opinions differ. Secretary of State Marco Rubio advocates for maximum pressure, though he expressed doubt about the regime's willingness to change. "Frankly, I don't see much progress," he admitted.

Vice President JD Vance disclosed in June that there are ongoing diplomatic talks between Washington and Havana to explore potential bilateral changes.

A Nation in Crisis and Political Calculations

The backdrop to these discussions is a Cuba in crisis: enduring blackouts of up to 25 to 30 consecutive hours, a projected GDP contraction between -6.5% and -7.2%, and an 80% to 90% reduction in fuel imports. The upcoming midterm elections in November 2026 are seen by analysts as a critical timeframe for Trump to demonstrate tangible results.

León, who predicted in April that Cuba will undergo a democratic transition in November, captured the collective anticipation with a telling phrase: "I believe silence speaks volumes. Yes, there are elements hidden beneath the surface."