Cuba Is Next. But Does Anyone Have a Plan?

Nobody asked. Trump said it anyway: "Cuba is going to fall pretty soon."

It was an offhand remark to a reporter last week, but in the context of 2026, nothing about it feels offhand. In January, the Trump administration successfully removed Venezuelan President Nicolás Maduro. Late last month, the US went to war with Iran. Now, less than three months into the year, Cuba has emerged as the next entry on what White House advisers are privately calling a winning streak. The president, according to people close to him, feels like he's on a roll.

The question isn't just whether Trump will move on Cuba. It's whether anyone—inside or outside the administration—has fully reckoned with what happens next.

Ninety Miles and Seventy Years

The geography hasn't changed. Cuba sits 90 miles from Key West, Florida—a fact that has haunted seven consecutive US presidencies, Democrat and Republican alike. John F. Kennedy learned this the hard way in 1961, when the Bay of Pigs invasion collapsed into one of the Cold War's most embarrassing foreign policy failures. Every president since has inherited the same unresolved tension: a communist government, close enough to see on a clear day, that Washington has never been able to dislodge.

Trump's focus on Cuba isn't improvised. It's embedded in his national security strategy and amplified by the man sitting beside him. Secretary of State Marco Rubio—grandson of Cuban exiles, political product of South Florida's Cuban-American community—has described ending the post-Castro regime as a lifelong mission. For Rubio, this isn't just geopolitics. It's personal history.

But the Cuba push also fits a broader pattern that the administration has been building since Trump's second inauguration: a doctrine of Western Hemisphere dominance. Annexing Greenland. Reclaiming the Panama Canal. Floating the idea of Canada as the 51st state. Each of these has been floated, in varying degrees of seriousness, as part of a single strategic vision—American supremacy in its own backyard. Cuba, in this framing, is the last major piece that doesn't fit.

The Plan (Such As It Is)

Here's the honest answer about what the Trump administration plans to do: nobody is entirely sure, possibly including the administration itself.

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What's clear is the end goal—the removal of Cuba's ruling government. What's murky is the method. Vivian Salama of The Atlantic, who has spoken with administration advisers extensively, describes a strategy built around attrition. The primary move so far has been cutting off Cuba's lifelines—starting with Venezuela. With Maduro gone, the oil and economic support that Havana depended on has been severed. The theory is that the Cuban regime is now being slowly suffocated.

From there, the White House sees three possible outcomes: the regime collapses on its own, its leaders choose to leave voluntarily with no other options remaining, or the US moves in directly in what advisers are describing as a "low-risk operation." The confidence in that last scenario is notable—and, to outside observers, somewhat striking given recent history.

The political timeline matters here too. Advisers are candid that the president's overseas operations carry electoral risk for Republicans on the ballot this November. The internal logic, as Salama reports it, is essentially: rip off the Band-Aid fast. Get the hard stuff done early, let the memory of conflict fade by summer, and campaign on victory. Whether that calculus holds is a different question.

What Could Go Wrong

Iran is already offering a preview. The US went in expecting a contained operation. What followed was missiles across the region, a destabilized Middle Eastern order, and a conflict that is still unfolding. Iran is a regional power with deep proxy networks—Cuba is not. But the lesson isn't about scale. It's about unintended consequences.

The most concrete risk in Cuba's case is a refugee crisis. A sudden collapse of the Cuban government could send tens of thousands of people toward Florida by boat. This creates a direct contradiction at the heart of Trump's own agenda: the administration has made hardline immigration enforcement its signature domestic policy. A wave of Cuban refugees would stress the very systems it has spent two years trying to tighten. The border crisis the president has repeatedly called "dire" could get significantly worse—as a direct result of his own foreign policy success.

There's also the question of what comes after. Regime change is the easy part to name. Post-regime stability is the part that tends to resist planning. Venezuela, even after Maduro's removal, remains politically fragile. Cuba's government has controlled the island's institutions for decades. When those structures go, what fills the space? History suggests the answer is rarely what the architects of regime change intended.

The Bigger Board

For readers tracking the broader geopolitical picture: Cuba is not just about Cuba. China has maintained economic and security ties with Havana for years. A decisive US move to flip Cuba into its orbit would be read in Beijing as a direct challenge—not just in the Caribbean, but as a signal about American appetite for confrontation in other contested spaces. How China responds, and where, is a variable the White House's Cuba calculus may be underweighting.

There's also the question of precedent. If the Trump administration successfully notches Venezuela, Iran, and Cuba in a single year, what does that model look like to other governments watching from the outside? And what does it signal to US allies—and adversaries—about the rules of engagement going forward?