Cuba Braces as Trump Doubles Down Despite Iran War Woes

As President Donald Trump intensifies pressure against Cuba, Havana’s hopes that the White House’s Iran war stalemate may deter the administration from coming through with promises of further action are fading.

Rather than postpone the heightened coercion campaign that began in January with an oil blockade shortly after the U.S. seized Venezuelan President Nicolás Maduro, a key ally and energy provider for Cuba, the Trump administration has upped the ante by dispatching the chief of the CIA to Havana. Washington is also reportedly preparing an indictment of former President Raúl Castro, brother of iconic Cuban leader Fidel Castro, who led the nation’s revolution in 1959.

Now, the communist-led island state just 90 miles off the coast of Florida is preparing for the worst.

“This has become a very strong interest to the White House, and it doesn’t appear to be going away or wavering,” Michael Bustamante, associate professor and director of Cuban Studies at the University of Florida, told Newsweek.

“If the Cuban authorities thought that they could sort of simply run out the clock, or that the midterm elections would come, or the Iran quagmire would distract them, the last even 48 hours have seemed to prove that wrong,” he said.

One Battle After Another

Cuba has long been in Trump’s sights. During his first administration, Trump reversed former President Barack Obama’s efforts to seek a thaw with the Cold War-era adversary and instead hardened a U.S. sanctions campaign in place for six decades.

Upon returning to office early last year, Trump continued his hard-line rhetoric on Havana. His decision to appoint former Florida Senator Marco Rubio as secretary of state-and later, national security adviser as well-signaled to many a tough track given the centrality of the issue to the prominent Cuban American conservative’s rise in the Republican Party.

Trump’s second term indeed turned out to be more interventionist than his first, though Cuba-at least initially-took a backseat to other foreign policy confrontations. The daring U.S. Delta Force raid in Venezuela first demonstrated Trump’s willingness to use force against rival heads of state, a commitment put on even deadlier display when the U.S. launched a joint war with Israel against another top rival, Iran, killing its supreme leader in the first day of the conflict.

And while the Middle East campaign remains volatile and far from settled, with neither Washington nor Tehran coming to terms despite global economic chaos due to the disruption of energy flow through the Strait of Hormuz, Trump has not lifted his focus on Cuba. The U.S. leader has openly teased that the country would be “next.”

Peter Kornbluh, senior analyst at the National Security Archive and director of the Cuban Documentation Project, predicted that Trump always intended to take on Cuba during his second administration.

“I think Cuba was a target that was planned even before the assault on Venezuela, and then Venezuela was seen as a steppingstone to Cuba, eventually, and I think once the United States was successful in Venezuela, it was a foregone conclusion that they would go after Cuba,” Kornbluh told Newsweek. “I thought Cuba would be next. It turns out Iran was next, but certainly I think they always planned to.”

How exactly Trump, who often balks at the idea of broadcasting his intentions, plans to pursue the issue remains opaque. The oil embargo has already wreaked havoc on the island, leading to regular, extended blackouts, shortages of crucial goods and services and debilitating transportation problems.

“There’s still quite a few steps of pain and destruction that the United States has left if it was to increase the pressure even more. Those range from isolating Cuba by cutting off U.S. air flights to an actual military attack,” Kornbluh said. “And what’s frightening I think about the pending indictment of Raúl Castro is that it sets a stage as it did in Venezuela for Maduro of kind of a legal fig leaf for some type of attack or operation against Cuba.”

A Not-So-Easy Target

When asked about the prospect of facing a U.S. military intervention, Cuban President Miguel Díaz-Canel told Newsweek last month his nation would “fight back,” channeling a guerrilla-style “war of all the people” doctrine to account for Washington’s vast military superiority.

Díaz-Canel also argued that the Cuban Communist Party’s ideological resilience and collective approach to leadership would serve to thwart plans to undermine the government through decapitation or subversion from within.

There is some merit to his boast. The Cuban defense and intelligence apparatuses have a formidable history of rooting out dissent that make it difficult for many to imagine a similar scenario emerging as in Venezuela, where Vice President Delcy Rodríguez swiftly took Maduro’s place and adopted a conciliatory approach to the Trump administration.

“I think it’s a lot harder to accomplish in Cuba because it’s a highly institutionalized communist political system with a collective leadership,” William LeoGrande, professor and Latin American specialist at American University, told Newsweek. “You could catch Miguel Díaz-Canel tomorrow and there’s a vice president that would step into his place and it’s not a Delcy Rodríguez. The vice presidents actually are all sort of long term, some of them going all the way back to the early days of the revolution.”

“It just works differently,” LeoGrande said. “I don’t think there is a single person who could command the loyalty of the armed forces, the security forces, the Communist Party bureaucracy, and the government bureaucracy in order to make the place run right, and I don’t think that there’s a person that the United States could sort of pluck out of obscurity, and install as the president of Cuba.”

The military option also has its pitfalls. While LeoGrande pointed out that the Cuban military is not likely to attempt to safeguard strategic points such as ports and airfields, an insurgency could raise the costs for the U.S. and complicate the goals of the mission in a way that obscures its success.

There is also the logistical hurdle. When the U.S. launched the operation to abduct Maduro, it did so with the backing of the largest build-up of naval power in the Caribbean since 1965, and much of these capabilities are currently devoted to the war in Iran.

An economic collapse, perhaps the most immediate threat to Cuba, would bring blowback as well.

“The regime itself is institutionally pretty strong, and I don’t see it collapsing as a political force, but social chaos will lead to one thing. It’s the one thing that it always leads to in Cuba. People get on boats and come north,” LeoGrande said. “And conceivably, if there’s real social violence, real chaos on the island, and the government can’t maintain social control, Cuban Americans are going to get out boats and go south to rescue their friends.”

“You’re going to have a combination of 1980 and 1994 together,” he added, referencing the Mariel boatlift and Balsero crisis that each saw tens of thousands of refugees flee the island to the U.S.

Fulton Armstrong, adjunct professorial lecturer and senior fellow at the Center for Latin American and Latino Studies also at American University, felt the risks may outweigh the benefits for the Trump administration.

“Its goal all along-to make Cuba a ‘failed state’ without triggering a humanitarian disaster-is simply unachievable,” Armstrong told Newsweek. “Its repeated flip-flops suggest awareness of that reality; we're getting different statements each day and, sometimes, every couple hours.”

“With Iran looking bad, the administration needs a victory, and some officials still seem to think-naively-that Cuba would go down as easily as Venezuela did. It won't,” Armstrong said. “Cuba is a very different country.”

Crisis on the Horizon

There is another date that looms large in Cuba’s collective memory of U.S. intervention. In April 1961, one year before the Cuban missile crisis put the island at the center of one of the most dramatic nuclear-charged standoffs between the U.S. and the Soviet Union, a CIA-backed invasion sought to topple Castro’s communist leadership in its nascent stages.

The so-called Bay of Pigs incident ended in failure. U.S. air support never arrived and counterrevolutionary fighters were soundly defeated, fueling Havana’s confidence in resisting U.S. intervention.

But much has changed in the past 65 years in ways that work in Washington’s favor.

“Modern technology plus Cuba’s proximity makes the situation today a world different than the Bay of Pigs era,” Evan Ellis, research professor of Latin American studies at the U.S. Army War College Strategic Studies Institute who previously served on the U.S. State Department’s Latin America planning staff, told Newsweek.

“Cuba is a relatively small country very close to the United States, and surrounded by U.S. military and surveillance assets,” Ellis said. “Even more than in Venezuela, through imaging, signals intelligence, and other capabilities, even before getting to operators on the ground, it is likely that the U.S. has enormous visibility over every person of interest, governmental organization and military or intelligence target of interest on the island.”

And unlike Iran, he said, Cuba’s location and size “means the president conceivably has options to capture or eliminate levels of leadership until they get to the people who will work with them.”

“As a compliment to President Trump, leaders such as Secretary of State Rubio have tremendous familiarity with, and resolve to address the Cuba situation,” Ellis said. “In calculating how far the U.S. will go with sanctions and potentially military action, I think the Cuban leadership understands that they stand directly between Iran and the November 2026 U.S. midterms.”

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This story was originally published May 16, 2026 at 1:00 AM.