
With ousted Venezuelan President Nicolás Maduro in custody in New York, and his decapitated regime in Caracas quietly cooperating with the United States, President Donald Trump has shifted his hostile refrain to Cuba.
“Cuba is a failing nation,” Mr. Trump has been saying recently. “It is down for the count.”
And with the Trump administration’s severing of Cuba’s Venezuelan oil lifeline – and a Jan. 29 executive order threatening stiff tariffs on any country supplying the island nation with oil – that assessment looks increasingly accurate.
Why We Wrote This
Deteriorating conditions in Cuba, amid the Trump administration’s aggressive posture toward the Western Hemisphere, are feeding a debate in Washington: Regime change or a deal? Experts say the latter is more likely, while a bigger strategic goal might be to curb China’s presence on the island.
The oil blockade has quickly led Cuba to enact harsh measures, including a halt to all public transportation, the declaration of a four-day work week, the closure of the tourist hotels that provided much-needed revenue, and mounting blackouts.
Families already enduring harsh living conditions are turning to wood and coal for cooking. Some international airlines have canceled their flights to the island.
The rapidly deteriorating conditions in Cuba are feeding an intensifying debate in Washington: deal or regime change? Should Mr. Trump go for a Venezuela-type bargain that leaves a cooperative segment of the existing government in place? Or should he squeeze until he brings down a communist regime that has been a U.S. bête noire since 1959?
The president’s rhetoric might suggest he favors the latter. Accordingly, some Cuban Americans have become suddenly rhapsodic over the prospects of an imminent return to rebuild a democratic and capitalist homeland, and perhaps reclaim properties they left behind some seven decades ago.
Gradual change vs. chaos
Yet anyone hoping for quick regime change in Havana is likely in for disappointment, many regional experts say.
Instead, most expect to see unrelenting U.S. economic pressure leading to some kind of agreement between the Trump administration and Cuban power brokers that favors gradual change on the island over sudden collapse and chaos.
Such a deal might be negotiated with the Cuban government. But for some former U.S. officials and experts, it’s more likely that meaningful talks would be – and if swirling rumors are correct, already are – held with other powerful circles. Among the candidates: senior military leaders, who have long held a tight grip on the economy, or “retired” decision-makers, including Raúl Castro, the former president and the late revolutionary leader Fidel Castro’s nonagenarian brother.
“Trump says we are talking to ‘the highest people in Cuba’ to get a deal, and that may or may not be true,” says Michael Rubin, a senior fellow in foreign policy at the American Enterprise Institute in Washington.
“But what we do know is that if we are talking to any real decision-makers, then it is not with the current president, [Miguel] Díaz-Canel, who is a mere figurehead,” he adds. “It would have to be with someone or a group that matters.”
Dr. Rubin says that could be with what he calls the “troika” – three aging former leaders led by Mr. Castro – or government officials who accept that a deal with the United States is inevitable. Or, with powerful military leaders willing to compromise with the U.S. to keep their share of the economy.
The real focus is China
Still, any discussion of a “deal” raises the question: In the case of Cuba, what is President Trump looking for?
Whereas the major strategic U.S. “get” in Venezuela was access to the country’s oil (and cutting it off from adversaries), what the Trump administration might be going for in Cuba is ouster not of the regime, some experts say, but of China.
“The more strategic goal here … is getting China but also Russia away from using Cuba as a forward operating base for their intelligence and even military activities,” says Christopher Hernandez-Roy, deputy director of the Americas Program at the Center for Strategic and International Studies in Washington. That goal, he notes, “is 100% in line with the recent National Security Strategy that zeroes in on removing China from strategic locations in the Western Hemisphere.”
“Trump is talking a lot about Greenland, and earlier about the Panama Canal and other places in the hemisphere,” he adds, “but there is no more strategic location than 90 miles off the Florida Keys.”
The Cuban government insists that China has no intelligence-gathering infrastructure on the island. But numerous U.S. government and national security think-tank reports over recent years have asserted that such spy bases indeed exist, as they do in other Latin American countries with close ties to China.
In the debate over deal vs. regime change, many experts and some officials willing to speak under condition of anonymity say the wild card in deciding which option will prevail is Secretary of State Marco Rubio, who was born in Miami to Cuban parents.
Mr. Rubio’s standing with President Trump has vaulted ever higher in recent months. And he has long advocated – as a Florida senator and as a political darling of the South Florida Cuban exile community – a policy aimed at ridding Cuba of the revolution that prompted so many Cubans to leave their homeland.
For its part, the Cuban government says that, while it is open to talks with the U.S. that are “respectful of Cuba’s sovereignty,” none are currently underway.
The Venezuela model
Yet some experts caution that, as much as the exile community and some of the president’s close associates could be pressing for regime change, Mr. Trump might be better served by considering the potential ramifications of moving in that direction – and by hewing closer to a Venezuela model of action.
“Bringing about regime change in Cuba has been the great white whale for many conservatives for a very long time,” says Rosemary Kelanic, an expert in energy security and U.S. grand strategy at Defense Priorities, a Washington think tank advocating a realist foreign policy. “This seems especially true in the South Florida Cuban community and in Trump’s circle of friends at Mar-a-Lago.”
“But while Trump is using oil to increase the pressure on the Cuban regime,” she adds, “I think the Venezuela model and Trump’s talk of a ‘deal’ suggests he could have something other than full regime change in mind.”
Dr. Kelanic says unrelenting pressure on Cuba risks destabilizing it and causing a humanitarian disaster just 90 miles off the Florida coast. “The consequences could include refugee outflows from Cuba into Florida,” she adds, “so there’s a real risk of blowback affecting an issue this administration cares about deeply.”
Forcing regime change would “require deploying the Marines to Cuba’s beaches, and that just isn’t in the cards for a president who is not in favor of boots-on-the-ground options,” says Mr. Hernandez-Roy. Instead, he foresees what he calls “regime management” that employs economic pressure to nudge gradual political change.
“Unlike Venezuela, Cuba has no democratic muscle memory to assist with quick political change,” he says.
As for who the Trump administration might turn to for meaningful talks, Mr. Hernandez-Roy says to keep an eye on Raúl Castro’s son, Alejandro Castro Espín, who was the Obama administration’s behind-the-scenes interlocutor on normalization of U.S.-Cuba relations.
Dr. Rubin notes that more than 2 million Cubans have fled the island in recent years, many of them professionals and members of the middle class, driven out by economic collapse. He says that group might be encouraged to return and participate in Cuba’s political and economic restructuring.
In terms of what Mr. Trump might want from any negotiations with Cuba, Dr. Rubin advises keeping in mind that the president is a real estate dealmaker who relishes the idea of accomplishing what other presidents couldn’t.
Especially appealing to Mr. Trump, he says, would be “putting hotels carrying his name on Cuba’s beaches.”
Those signs would be a constant reminder that while Cuba’s communist government stymied 12 U.S. presidents, it was President Trump who finally defeated it.



