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Regime Change in Cuba Appeals to Trump but Carries Risks

February 27, 2026
in News
Regime Change in Cuba Appeals to Trump but Carries Risks

With a U.S. chokehold pushing Cuba’s economy toward potential collapse, President Trump is hoping to reach a deal with the island’s communist government to avoid chaos even if it means the leadership change long sought by many of his close allies has to wait.

Instead, Mr. Trump appears to be pursuing a version of his approach to Venezuela, whose leftist government remained in power after U.S. troops captured its president, Nicolás Maduro, in January.

On Wednesday, Cuban border guards shot and killed four Cuban nationals who departed from the United States as they approached the island’s coast in a boat. It is unclear whether the episode will affect the Trump administration’s plans.

After years of calling for Venezuela’s opposition leaders to take power, Mr. Trump has cooperated with Mr. Maduro’s successor to gain American access to the country’s oil, leaving questions about a political transition for later.

Similarly, Mr. Trump does not want a sudden power vacuum in Havana, according to a senior administration official and an associate of Secretary of State Marco Rubio, as well as Mr. Rubio’s own public remarks in recent weeks. Mr. Rubio has spoken about a potential deal with Raúl Guillermo Rodríguez Castro, the grandson of Fidel Castro’s brother, Raúl, according to two people familiar with the matter.

Mr. Rubio, who steers Mr. Trump’s Latin America policy, is a son of Cuban immigrants who has long called for the government’s downfall. But after a meeting with Caribbean leaders on Wednesday, Mr. Rubio sounded willing to wait.

“Cuba needs to change,” Mr. Rubio said. But, he 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,” he added.

Arguing that the island’s socialist economic model is unsustainable, Mr. Rubio signaled that the United States might settle for initial change in that area. “If they want to make those dramatic reforms that open the space for both economic — and eventually, political — freedom for the people of Cuba, obviously the United States would love to see that,” he said.

That approach might stand a better chance of success than U.S. demands for Cuba’s sudden political transformation. Cuba’s government says it is willing to negotiate with Mr. Trump on a range of issues. But Havana insists it will not discuss Cuba’s Constitution or matters of “sovereignty.”

In contrast to his approach to Venezuela, however, Mr. Trump has not threatened Cuba with military action. And while few predicted the nighttime raid that captured Mr. Maduro, repeating such a daring operation would be extremely difficult.

“They’re not looking for overnight regime change,” said Ryan Berg, the director of the Americas Program at the Center for Strategic and International Studies. The administration’s goal, he added, appears to be “a slow transition” from Cuba’s authoritarian dictatorship to democracy.

As Mr. Trump considered options for Venezuela, U.S. officials feared that abruptly installing an opposition government could trigger violence, chaos and a humanitarian crisis, as predicted by U.S. war games.

The same worries apply to Cuba, where economic collapse or a political vacuum could lead to violent anarchy and perhaps unleash a flood of seaborne refugees toward Florida. Past waves of Cuban refugees, in 1980 and the mid-1990s, caused political crises for Presidents Jimmy Carter and Bill Clinton.

Asked on Wednesday about the potential for a humanitarian crisis and a new migration wave, Mr. Rubio acknowledged the concern. “As far as spillover effect, they’re not more concerned than we are,” he said. “We’re 90 miles away, and the U.S. has experienced mass migration from Cuba in the past.”

In an apparent effort to blunt the growing toll of U.S. pressure, the Trump administration said on Wednesday that it would allow the resale of Venezuelan oil to Cuba, so long as the transactions were made with Cuba’s private sector and did not benefit the island’s government.

Mr. Trump has thrown Cuba’s economy into a spiral by cutting off the island’s access to foreign oil. First, after capturing Mr. Maduro, Mr. Trump forced Venezuela — which had long been Cuba’s primary source of oil — to stop shipping crude to Havana.

Then, Mr. Trump issued an executive order on Jan. 29, threatening to impose tariffs on any country that sold or provided oil to the island, citing Cuba’s ties to Russia and China, links to terrorist groups and political repression. Mexico, Cuba’s last major supplier, has not sent any more oil.

Cuba has since reduced its work and school weeks and says it can no longer refuel foreign airliners. The crisis, analysts say, may be the gravest threat to the Cuban government’s survival since Fidel Castro’s communist revolution prevailed in 1959.

In Washington and South Florida, many Cuba hawks are eagerly anticipating the island’s long-awaited liberation. “Cuba’s day of freedom is closer than ever,” Representative María Elvira Salazar, a Miami-area Republican, recently wrote on social media. Her post featured an image of a bald eagle swooping toward a Cuban flag.

Mr. Rubio’s more measured rhetoric has surprised some analysts, after his many years of calling for an end to Cuba’s “brutal dictatorship.” So has his focus on economic reform, given his response when President Barack Obama relaxed U.S. trade sanctions on the island in 2015 as part of a larger effort to repair relations with Havana.

Mr. Rubio, then a Florida Republican senator, slammed what he called “the lie and the illusion that more commerce and access to money and goods will translate to political freedom for the Cuban people.” Mr. Rubio has since claimed vindication, noting that Mr. Obama’s outreach did little to change the nature of Cuban government or society. (Mr. Trump reversed Mr. Obama’s policies during his first term as president.)

In his recent conversation with an associate, Mr. Rubio also said the U.S. had struggled to identify a Cuban equivalent to Delcy Rodríguez of Venezuela, the former vice president who succeeded Mr. Maduro and has been cooperating with the Trump administration’s moves to control the country’s oil.

It is unclear whether he believes he has since found that person in Mr. Rodríguez Castro, a high-ranking state security official in his early 40s who goes by the nickname of “El Cangrejo,” or “The Crab.” Mr. Rubio’s conversations with Mr. Rodríguez Castro were reported earlier by Axios.

Mr. Rodríguez Castro’s grandfather, Raúl, officially assumed power in 2008 from his brother Fidel, who died in 2016. The country has been governed by President Miguel Díaz-Canel since 2018.

“The point is that within the Cuban system there are individuals who realize that the project is already ending and who may be interested in making a change that they see as necessary,” Mike Hammer, the top U.S. diplomat in Havana, was quoted telling the Spanish newspaper ABC on Feb. 22.

Cuba’s government did not respond to requests for comment about its contacts with the Trump administration.

Mr. Díaz-Canel has said he is open to dialogue with the United States “without pressure or preconditions.” But he is also a Castro family protégé who has vowed to defend their communist system. “Cuba does not kneel,” he told the state-run newspaper Granma earlier this month.

Several Cuba analysts doubted that Mr. Trump could find a willing partner in Havana similar to Ms. Rodríguez. After nearly 70 years in power, Cuba’s communist leadership has deeper, more hardened roots than Mr. Maduro’s regime, which traces its origins to the late 1990s.

“The search for a Cuban Delcy Rodríguez is a fool’s game,” said William LeoGrande, a professor at American University who specializes in Latin America. “If there’s going to be a deal it’s going to have to be between the United States and the current Cuban government — not some rump of the current government.”

Unlike Venezuela, Cuba’s repressive one-party dictatorship has left the country with no political opposition. “Everyone is in jail or in exile,” said María José Espinosa, a Cuban-born senior fellow at the progressive Center for International Policy.

Still, some Trump officials believe that Cuba’s leaders will be forced to make concessions to Mr. Trump. The alternative — an economic collapse and potential violent uprising — would be worse for them.

At a Feb. 18 press briefing, Karoline Leavitt, the White House press secretary, was asked whether Mr. Trump would settle for anything less than regime change in Cuba. Ms. Leavitt said that it was in America’s “best interest to have Cuba be a truly free and prosperous democracy.”

“They are a regime that is falling,” she added. “Their country is collapsing and that’s why we believe it’s in their best interest to make very dramatic changes very soon.”

Jason Marczak, a Latin America expert at the Atlantic Council in Washington, agreed that engineering a transition away from Cuba’s communist government would be very difficult. “Most Cubans have never lived under anything other than a communist regime,” he said.

But he said that Mr. Trump and Mr. Rubio might be more willing to accept the risk of a chaotic transition in Cuba than they were in Venezuela. Whereas Mr. Trump wants a stable environment to protect Venezuela’s future oil production, from which he hopes the U.S. can profit, Cuba has an isolated economy with few exports; unrest there would have little economic impact beyond its shores.

Mass migration, Mr. Marczak added, can be mitigated with humanitarian aid — which the Trump administration has already begun sending to the island, working with the local Catholic church to circumvent Cuba’s government.

Such concerns are not new. At an earlier moment of economic crisis in Cuba, a U.S. National Intelligence Estimate warned about the potential fallout from a government collapse.

“U.S. interests will be challenged in complex and possibly unprecedented ways,” the since-declassified document said.

Any change in power would likely mean “substantial and possibly protracted instability,” including violent retribution, it added, while predicting “large-scale emigration to the United States” and “demands for U.S. involvement” to clean up the mess.

The document is also a reminder that Cuba has defied countless predictions of its imminent collapse.

“There is a better than even chance Fidel Castro’s government will fall within the next few years,” the intelligence document concluded. That was in 1993.

Julian E. Barnes, Frances Robles and Anton Troianovski contributed reporting.

Michael Crowley covers the State Department and U.S. foreign policy for The Times. He has reported from nearly three dozen countries and often travels with the secretary of state.

The post Regime Change in Cuba Appeals to Trump but Carries Risks appeared first on New York Times.

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