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By David Averre
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Time travel doesn’t exist as far as we know, but take a visit to Cuba and you’ll certainly feel like you’re stepping into history.
The U.S. has maintained an economic embargo on the island just 90 miles off its coastline for 64 years, hoping to force Havana’s communist leaders to capitulate. For 64 years, it hasn’t worked. Cuba’s rulers haven’t budged, but life for ordinary Cubans has become increasingly difficult as the world around them slowly crumbles.
Then in January, Venezuela’s President Nicolás Maduro and his wife were plucked from their compound in the dead of night and whisked away in a brazen, likely illegal—and highly successful—U. S. military operation. Decades of antagonism between Washington and Caracas evaporated in a matter of weeks, and before long Maduro’s deputy had granted Washington sweeping control over some of Venezuela's richest oil fields.
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For weeks after Maduro’s capture, the rhetoric pouring out of the White House suggested Cuba was but the next domino to fall in Donald Trump’s Donroe Doctrine master plan. But in late February, American forces went to war in a different part of the world, and Havana all but disappeared from Trump’s agenda.
Now, the U.S. president says he’ll take care of Cuba on the way back from Iran, as if the United States can simply stop by and collect another victory. Reality begs to differ: nearly 10 months after Maduro’s capture, Cuba’s government remains firmly in power, its diplomats are squaring up to American representatives at the United Nations, and Washington appears no closer to achieving its original ambitions.
The Long Game
Cuba may have slipped down Trump’s list of talking points, but the White House’s pressure campaign against Havana has quietly churned along in the background.
Since January, Washington has systematically tightened economic restrictions on the island. First came the cutoff of Venezuelan oil supplies and threats of tariffs against other countries providing fuel. Then came an expanding campaign of sanctions against Cuban officials, state enterprises and foreign companies doing business with Havana.
The consequences have been devastating. Cuba’s national electricity grid suffered at least six partial or complete collapses between January and September, with rolling blackouts sometimes lasting more than 24 hours. Politically, however, Washington has little to show for it.
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"I do think the war in Iran fundamentally altered the calculation around Cuba, because military assets which had been deployed in the Caribbean to address Maduro were needed elsewhere, and because the highly unpopular nature of the Iran war would make military action in Cuba more politically risky if it were not an immediate success like in Venezuela," Christopher Hernandez-Roy, acting director of the Americas Program at the Center for Strategic and International Studies (CSIS), told Newsweek.
Still, the president is promising another spectacular triumph. At a pre-midterm rally in Florida on October 23, Trump suggested American warships returning from Iran would stop just off Cuba’s coastline, forcing Havana’s leaders to surrender before Marco Rubio sails in to finalize the deal.
The secretary of state is operating on a different timetable, however. In August, Rubio said Washington was systematically closing off Havana’s economic escape routes, declared the Trump administration was in no rush for a quick victory, and insisted the White House was setting Cuba on an irreversible path to transformation by 2028.
"Rubio has been concerned about Cuba his entire political life and understands the island and the US-Cuba dynamic intimately. For him, moving Cuba from dictatorship to freedom and eventually democracy, it’s deeply personal," Hernandez-Roy said.
Rubio certainly has a strong incentive to take his time. With Trump constitutionally barred from seeking another term, Rubio is among the Republicans touted as potential successors in 2028.
"Certainly, some real tangible change in Cuba ahead of the next presidential elections could boost Rubio’s electoral appeal—though I’ll repeat that the issue is deeply personal first and foremost," Hernandez-Roy added. "I definitely think he is playing a longer game than President Trump, where gradual economic opening and more freedom for the private sector to turn the economy around in tandem with political opening will bring change."
But this strategic patience has not been universally welcomed.
"It has left some of his supporters in Miami and the Cuban-American community a little bit unnerved and rattled," said Michael Bustamante, a historian and director of the Cuban Studies Program at the University of Miami. "They have been calling for more dramatic, military action. Rubio has called for strategic patience."
Sebastián Arcos, director of the Institute for Cuban Studies at Florida International University, told Newsweek that Trump’s bombast and Rubio’s pragmatism are not necessarily at odds. "I see the dual approach as part of the same plan: intimidate and strangulate. I believe part of the plan is to stimulate cracks within the regime and erode confidence in its survivability."
Different Beasts
Whether Washington’s approach to Cuba is a carefully coordinated strategy or a clash between two men with different priorities, the underlying problem remains the same: Havana is a much tougher nut to crack than Caracas.
The operation to capture Maduro was an extraordinary demonstration of American military capability, but the achievement owed as much to Venezuela’s political circumstances as it did to the prowess of U.S. special forces.
His removal did not dismantle the Venezuelan government. Vice President Delcy Rodríguez assumed control, and much of the existing political and security apparatus remained intact; Washington simply needed those who inherited power to cooperate with its demands. Cuba offers no such convenient arrangement.
"I absolutely think President Trump was amazed at the ease with which Nicolás Maduro was removed from power, so much so that it was only a few days later that he announced that Cuba would be next. But Venezuela is not Cuba," Hernandez-Roy said. Bustamante added: "The Cuban government is a true one-party state. I would argue that the Venezuelan government never was."
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Even under Maduro, Venezuela maintained the remnants of a multiparty political system. Opposition parties could organize and contest elections, albeit under extraordinary restrictions and frequent repression. Cuba’s Communist Party has spent almost seven decades eliminating those opportunities.
Political authority in Cuba is concentrated within a deeply entrenched network of party officials, military commanders and intelligence chiefs. Independent opposition movements have no comparable institutional foothold, while the armed forces control substantial portions of the national economy.
"Despite the ideological intimacy between the two, Venezuela never became fully totalitarian. That allowed the Venezuelan opposition to organize and win an election in 2024 against all odds. That could never happen in Cuba," Arcos said.
Removing President Miguel Díaz-Canel, or even 95-year-old revolutionary leader Raúl Castro, would not necessarily produce a cooperative replacement. It could just as easily bring harder-line figures to power—a lesson Washington has endured following its killing of Iran’s Supreme Leader Ali Khamenei in February.
Talks with figures close to Raúl Castro, including his grandson, have failed to produce a diplomatic breakthrough. Havana has approved sweeping economic reforms under American pressure, but stopped well short of the political concessions Washington demands. Nor has the White House publicly offered a clear set of conditions under which Cuba’s existing leaders could make major concessions without risking their own survival.
"The priority of this regime has always been absolute power, even over the welfare of the Cuban people, and no alternative where they don’t have absolute power will be acceptable for them. They will never negotiate their own surrender. It’s the nature of the regime," Arcos concluded.
Cuba’s government has already survived the Soviet Union’s collapse, the devastating economic crisis that followed and more than six decades of U.S. sanctions and diplomatic hostility. Its leaders clearly believe they can survive one more American president—even if this one is a bit louder and more unpredictable than all who came before him.
The Waiting Game
While this protracted confrontation between Washington and Havana unfolds, ordinary Cubans are paying a steep price.
The island’s economy was already in serious trouble before Trump ratcheted up the pressure following years of economic mismanagement, chronic underinvestment and the fallout of the COVID-19 pandemic. Now, American fuel restrictions and sanctions have compounded shortages of food, medicine and electricity.
But Washington may soon be forced to pay a price, too.
"It is still possible that the U.S.’ increasing sanctions will create enough pressure on the regime for some negotiated changes," Hernandez-Roy said. "But the time that takes will need to be calibrated against the cost of Cuba’s deteriorating humanitarian situation, and as it deepens, at some point the United States will be blamed, rather than placing the blame on the disastrous policies of the Cuban regime."
Even if Havana eventually makes concessions, what exactly constitutes victory for Washington?
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Trump could conceivably declare success if Cuba installs a more cooperative leader and opens its economy to American investment. Rubio and many of his Cuban-American supporters, however, have spent decades campaigning for a fundamental transformation of Cuba’s political system.
"I think the question is ‘victory’ for whom in DC," Hernandez-Roy said. "Whether that change leads to sustained political change on the island I think might be secondary for President Trump, but of equal or greater importance to Secretary of State Rubio than an improved economic relationship."
For now, neither Washington nor Havana has much to celebrate. At the United Nations last week, Washington managed to erode some support for the resolution condemning America’s blockade of the island, securing 17 votes against and 25 abstentions. Still, it’s a long way off the 130 countries that voted in favor of lifting American sanctions.
And so the limbo continues. Cuba’s government remains firmly in power, but its economy is collapsing around it. Rubio is playing for a political transformation that could take years, while Trump seems convinced that a decisive victory is just around the corner.
Caught between a government that refuses to concede and a superpower that cannot compel its surrender are millions of Cubans, waiting for a future neither side seems able to deliver.
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