Trump’s Cuba Policy: Why Decapitation Won’t Work | Andrés Velasco

by mark.thompson business editor

The decades-long effort to destabilize Cuba, a strategy rooted in the belief that removing its leadership will resolve deep-seated economic and political issues, continues. As Andrés Velasco points out, this approach – exemplified by past CIA schemes and now, arguably, by the current U.S. Administration’s policies – fundamentally misunderstands the nature of the Cuban state and the resilience of its system. The focus on “decapitation” tactics ignores the underlying factors driving Cuba’s challenges and offers no viable path toward meaningful change. Understanding the history of these attempts, and their consistent failure, is crucial to evaluating current strategies and considering alternative approaches to U.S.-Cuba relations.

Velasco’s argument, published March 25, 2026, draws a direct line from the outlandish plots of the 1960s – poisoned cigars, exploding seashells – to the more subtle, yet equally aimed, efforts of today. While the methods have evolved, the core assumption remains the same: that eliminating the figurehead will dismantle the entire structure. This perspective, he contends, is not only historically inaccurate but also strategically flawed. The enduring challenge in Cuba isn’t simply a matter of leadership; it’s a complex interplay of economic constraints, political ideology, and a deeply ingrained national identity.

A History of Failed Interventions

The CIA’s attempts to overthrow Fidel Castro, documented extensively in declassified files, were remarkably ambitious and ultimately unsuccessful. The CIA’s own records detail a series of plots, ranging from the bizarre to the genuinely dangerous, all predicated on the idea that Castro’s removal would trigger a collapse of the Cuban revolution. These included attempts to sabotage sugar crops, disrupt communications, and, of course, assassinate the leader himself. The agency even explored the possibility of spreading a disease that would cause Castro’s beard to fall out, hoping to damage his public image. None of these efforts achieved their intended outcome.

These early failures weren’t simply due to poor execution. They underestimated Castro’s popular support, the Cuban government’s ability to adapt, and the broader geopolitical context of the Cold War. The Cuban revolution, fueled by widespread discontent with the Batista regime and a desire for social justice, had tapped into a deep well of national sentiment. Removing Castro wouldn’t erase those underlying conditions.

The Current Approach and Its Limitations

While the methods employed by the Trump administration, as Velasco suggests, are less flamboyant than exploding seashells, the underlying strategy remains remarkably similar. The focus has been on tightening economic sanctions, restricting travel, and increasing pressure on the Cuban government through diplomatic isolation. These measures, proponents argue, aim to weaken the regime and create conditions for a transition to democracy. Yet, the impact of these sanctions has been largely to exacerbate the economic hardships faced by ordinary Cubans, rather than to destabilize the government.

According to a Reuters report from June 2021, the tightening of sanctions coincided with a period of increased social unrest in Cuba, fueled by shortages of food, medicine, and other essential goods. While the protests were significant, they did not lead to the collapse of the government, and the Cuban authorities responded with a crackdown on dissent. This illustrates a key point: economic pressure, while causing hardship, can also strengthen the government’s resolve and provide a justification for increased repression.

The Role of Miguel Díaz-Canel

Velasco specifically points to the futility of targeting Cuban President Miguel Díaz-Canel. While Díaz-Canel represents the continuity of the communist regime, he is not the sole source of its power. He inherited a system built over decades, with deep roots in Cuban society and a robust security apparatus. Removing him would likely be followed by the swift appointment of a successor, and the underlying problems facing Cuba would remain unresolved.

Díaz-Canel assumed the presidency in 2018, succeeding Raúl Castro, who had taken over from his brother Fidel in 2006. Britannica’s profile of Díaz-Canel details his rise through the ranks of the Communist Party and his commitment to maintaining the socialist system. He represents a generational shift in Cuban leadership, but not a fundamental change in ideology or policy.

Beyond “Decapitation”: A More Constructive Path

Velasco’s critique implicitly calls for a reassessment of U.S. Policy toward Cuba. Instead of focusing on regime change, a more constructive approach would involve engagement, dialogue, and a willingness to address the legitimate concerns of both sides. This could include easing travel restrictions, promoting economic cooperation, and supporting civil society initiatives that promote human rights and democratic values. It would also require acknowledging the historical grievances that have fueled mistrust and animosity between the two countries.

Such an approach wouldn’t guarantee a swift or easy resolution to Cuba’s challenges. But it would offer a more realistic and sustainable path toward positive change than the failed strategies of the past. The lesson of the poisoned cigars and exploding seashells – and the more subtle tactics of today – is clear: simply removing the leader won’t fix what ails Cuba. A more nuanced and comprehensive approach is needed, one that recognizes the complexity of the situation and prioritizes the well-being of the Cuban people.

Looking ahead, the Biden administration’s approach to Cuba will be a key indicator of whether the U.S. Is willing to learn from past mistakes. The next significant development to watch will be the outcome of the ongoing review of U.S. Policy toward Cuba, expected to conclude in the coming months. The results of this review will likely shape the trajectory of U.S.-Cuba relations for years to come.

What are your thoughts on the future of U.S.-Cuba relations? Share your perspective in the comments below.

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