Ninety miles off Florida, Cuba is wobbling, and President Donald Trump faces a choice: push the island toward crisis or try to steady it before everything slips out of U.S. control.
Cuba is enduring its worst economic collapse in decades. Power grids fail for hours. Fuel is scarce. Food is hard to find. Work and school weeks have been reduced. There are fears of a surge in migration toward the U.S. The state feels brittle and close to breaking.
In Washington, the debate isn’t whether U.S. pressure is hurting Havana — it clearly is — but whether America can control what happens next.
Since returning to office, Trump has tightened sanctions, reinforced travel bans and targeted oil supplies to squeeze the Cuban government. The measures echo his broader “America First” foreign policy and play well with hard-line Cuban-American voters in Florida. The strategy appears to be that if Havana is pressured hard enough, its leaders will be forced to change or forced out.
But pressure is not the same as control. That is Trump’s conundrum.
There’s a clear Venezuela comparison. Earlier this year, Trump launched an operation that led to the removal of Venezuela’s President Nicolás Maduro — a dramatic demonstration of U.S. power in the region. But what followed in Venezuela showed the limits of such tactics: Maduro’s ouster did not quickly produce stable governance or a successful democratic transition. Instead, it left a messy political vacuum that has been filled by a Maduro acolyte, whose commitment to changing Venezuela is uncertain.
That lesson looms over Cuba. At a Caribbean summit in St. Kitts and Nevis earlier this week, U.S. Secretary of State Marco Rubio insisted that Cuba’s humanitarian crisis has been caused by the island’s own government policies, not by a U.S. oil blockade on Venezuela.
“Cuba needs to change,” he said, but added, “it doesn’t have to change all at once. It doesn’t have to change from one day to the next. Everyone is mature and realistic here.”
“We’re seeing that process play out, for example, in Venezuela.”
The U.S. intervention in Caracas dramatically cut off Venezuela’s oil exports, a crucial lifeline for Cuba’s fragile economy, and deepened Havana’s energy crisis.
The oil situation in Cuba has become a central part of the Trump administration’s pressure campaign. Cuba relies heavily on imported fuel for electricity, transportation and basic services, and decades of U.S. sanctions have already weakened its ability to meet energy needs on its own. In early 2026, after the U.S. intervention in Venezuela and the removal of Maduro, shipments of Venezuelan oil stopped, contributing to widespread blackouts and deepening the island’s economic crisis.
In a recent shift, the U.S. Treasury said it will allow licensed companies to resell Venezuelan oil to Cuba only if it benefits the Cuban private sector, not the state or military, signaling an attempt to ease civilian hardship without strengthening the communist government.
The policy seeks to ease hardship for ordinary Cubans while keeping up the squeeze on the government in Havana, but it will be hard to separate the two.
The risk is that Cuba’s growing pressures — economic decline, blackouts and public anger — could spiral into chaos. If protests spread or the security forces lose control, unrest could escalate quickly. That could mean mass migration toward Florida or dangerous incidents at sea that Washington would have to respond to fast. Once events start moving, the U.S. might struggle to shape the outcome.
That danger was highlighted on Wednesday when Cuban forces killed four armed exiles and injured six more on a Florida-registered speedboat, sharply raising tensions.
Rubio has pushed back on claims that American policy is to blame. “What the Cuban people should know is this: that if they are hungry and they are suffering, it’s not because we’re not prepared to help them. We are. It’s that the people standing in the way of us helping them is the regime, the Communist Party,” he said.
The question for Washington is whether it should act decisively now to force political change, and try to control the outcome, or risk being overtaken by events.
Restraint in U.S. policy carries dangers. If Washington waits too long to act or sends mixed signals about its goals in Havana, rivals such as China and Russia could step in to stabilize Cuba on their own terms.
Moscow has publicly condemned U.S. pressure on Cuba and reaffirmed its political and material support for the island, calling American tactics unacceptable and pledging continued assistance.
At a meeting with Cuban Foreign Minister Bruno Rodriguez in Moscow earlier this month, Putin said of the restrictions: “You know how we feel about this. We don’t accept anything of the sort.”
“We have always been on Cuba’s side in its struggle for independence, for the right to chart its own path of development, and we have always supported the Cuban people,” he said.
Beijing has also voiced its backing, saying it will “do what it can” to support Cuba and opposing external interference in its affairs, even as it stops short of announcing specific fuel deliveries.
Both countries have longstanding ties with Havana and strategic reasons to counter U.S. pressure. Their involvement could reshape regional dynamics if Cuba’s crisis deepens.
In Venezuela, U.S. intervention did not deliver fully controllable results. Removing Maduro was dramatic, but it did not create stability or a smooth democratic transition. The aftermath is uncertain.
Cuba could prove even more complicated. It has had a tightly controlled Communist system since the 1950s, its economy is fragile and its society is already under strain. If sudden change comes, it could lead to major turmoil.
That is Trump’s dilemma: push hard and risk unleashing chaos or hold back and risk losing influence.
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