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[The Brink of Collapse: The Trump Administration's Escalating Pressure on Cuba]-[After Venezuela, Is Cuba Next?]

The Daily · B2 · 2026-02-17

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📋 Summary

The Brink of Collapse: The Trump Administration's Escalating Pressure on Cuba

For over six decades, the United States has maintained a persistent, albeit largely unsuccessful, quest to topple the communist regime in Cuba. However, current reporting suggests that the island is facing its most precarious moment in 67 years. Under the Trump administration, the U.S. has moved beyond traditional embargoes toward a strategy of systematic economic strangulation, aiming to force radical change on the island.

The Anatomy of an Unsustainable Crisis

Experts and economists have long jokingly referred to the "short index fingers" of Cubans, worn down from decades of tapping tables while waiting for the regime's collapse. Yet, the consensus among observers today is that the current situation is "unsustainable." The island, which produces only 40% of its domestic fuel, has been pushed to the edge by the loss of its primary energy lifelines. Following U.S. pressure, Venezuela—Cuba’s longtime benefactor—has ceased shipments, and recent tariffs imposed by the Trump administration have pressured Mexico to follow suit. The result is a looming humanitarian crisis: schools are reducing schedules, hospitals are struggling, and the transportation sector is effectively paralyzed.

Historical Context: From Bay of Pigs to the "Special Period"

Since the 1960s, the U.S. has viewed Cuba as the "antithesis" of its values, citing the confiscation of U.S. industries and the alignment with the Soviet Union as primary grievances. The U.S. history of intervention is vast, ranging from the failed Bay of Pigs invasion to the clandestine CIA attempts to assassinate Fidel Castro. Historically, the regime survived by using migration as an "escape valve," most notably during the 1980 Mariel Boatlift, and by relying on external subsidies—first from the Soviet Union, and later from Venezuela. Even during the post-Soviet "special period" of the 1990s, the regime managed to endure, leading many to believe that the U.S. strategy of internal pressure was insufficient.

The Marco Rubio Factor

Central to the current escalation is Secretary of State and National Security Advisor Marco Rubio. As a Cuban-American whose political identity is forged in the vituperatively anti-Castro exile community of South Florida, Rubio views the toppling of the Cuban regime as his ultimate "crowning legacy achievement." His strategy involves cutting off the "oil supplies to Havana" by neutralizing Venezuela, effectively starving the Cuban government of the resources needed to sustain its patronage system.

The Dilemma of Regime Change

Despite the administration's aggressive stance, the path forward remains fraught with danger. Analysts warn that Cuba’s political system is "monolithic" and "brittle," with no clear alternative leadership. A sudden collapse risks triggering "total chaos, violence, and mass migration" toward Florida. While the administration hopes for a "soft landing"—perhaps through internal reform—experts argue that expecting the regime to negotiate its own demise is a "fool’s errand." The Cuban leadership has mastered the art of "buying time" through empty promises, a pattern the Trump administration seems determined to break.

Conclusion: A Historic Triumph?

Ultimately, the Trump administration’s bet is that by applying unprecedented economic might, it can succeed where predecessors from Eisenhower to Obama failed. While most Americans do not prioritize Cuba in their daily concerns, a successful transition away from the communist government would be viewed as a historic foreign policy triumph. Whether this strategy leads to a democratic opening or descends into a humanitarian catastrophe remains the most significant question for the region's future.

🎯Key Sentences

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I actually looked it up today.
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Does that feel right to you?
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A hundred percent.
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Well, I don't know why.
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So what are people supposed to do?
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📝Key Phrases

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pushing the country to the brink
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playing out on the island
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cries uncle
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dead set on
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antithesis of
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📖 Transcript

From The New York Times, I'm Natalie Kittroff.
This is The Daily.
For more than six decades, the United States has tried and failed to topple the regime in Cuba.
But after ousting Cuba's closest ally, Nicolas Maduro, and pushing the country into dire economic crisis, the Trump administration is closer than ever to forcing radical change on the island.
Today my colleagues Francis Robles and Michael Crowley on how this latest escalation is pushing Cuba to the brink.
And whether this time, finally, the U.S. government will get what it wants.

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