Cuba’s regime is now in Donald Trump’s sights

IT IS TRADITIONAL at the turn of the year for Cuban-Americans in Miami to gather around a pig roast and toast “Next year in Havana”. This started in 1959 after Fidel Castro, a communist revolutionary, seized power in Cuba and drove many of its people into exile. Then, the toast reflected recent emigrants’ earnest desire to return, and their belief that Castro would soon fall, allowing them to do so. As time proved Castro’s regime to be incredibly resilient, the toast’s hope decayed into wistfulness.

This year is different. As Miami’s other large group of exiles, Venezuelans, took to the streets to celebrate the capture of their country’s dictator, Nicolás Maduro, by American forces during an extraordinary nighttime raid on January 3rd, the Cuban diaspora was cheering, too. They hope that the men who have made their country miserable, prompting the recent emigration of a quarter of the country’s population, may be next on Donald Trump’s list of problems in his hemisphere that he is willing to solve by force. “We are overwhelmed with emotion and hope,” Carlos Gimenez, a Cuban-American Republican congressman, wrote on X, a social-media platform. The most excitable exiles compare Mr Maduro’s departure to the fall of the Berlin Wall in 1989, presaging a toppling of leftist regimes across Latin America.

The excitement is fuelled not just by the fact of Mr Maduro’s capture, but by strong suggestions from the Trump administration that Cuba could be next. “If I lived in Havana and was in the government, I’d be concerned,” Marco Rubio, the secretary of state, said at the press conference in Mar-a-Lago after Mr Maduro’s capture. A second-generation Cuban-American from Miami, Mr Rubio has been a tireless advocate for ending Communist rule in Cuba. Cuba, Mr Trump said, is “going to be something we’ll end up talking about”.

It is more vulnerable to external pressures for regime change today than at any time since the early 1990s, when its benefactor, the Soviet Union, collapsed and the island fell into a “Special Period” of belt-tightening. For a while, oil-rich Venezuela helped keep Cuba afloat. But in recent years mismanagement of Venezuela’s petroleum industry and international sanctions caused shipments to Cuba to fall by almost three-quarters, from more than 100,000 barrels per day (b/d) in 2021—about 80% of its domestic needs—to 16,000 b/d in 2025.

Cuba was already struggling when covid-19 set back its tourism industry, which had begun to boom after Barack Obama normalised the United States’ relations with Cuba in 2015. The sudden loss of foreign earnings led to a collapse of basic services. Food production fell sharply due to lack of cash for fertiliser and farm equipment, exacerbated by price controls that left farmers with no incentive to produce. Rubbish collection has become the biggest popular complaint as mountains of waste rot in the streets. Daily power outages, a result of worn-out Soviet-era diesel generators and scant oil imports, make life on the island a misery. An independent Cuban journalist, Yoani Sánchez, reported this week that top officials were warned in high-level meetings at the end of 2025 that “the State can no longer provide many entities with even the minimum resources they need to continue operating”.

Cuban officials have called for international condemnation of the “criminal” American operation to snatch the Maduros. But, as more details of the attack come out, it’s hard to say which regime has more to mourn. The operation was a stunning failure by Cuba’s vaunted military-intelligence and security apparatus, which was said to be shielding the Venezuelan leader. Cuba says 32 of its soldiers and security agents died “combating” the American attack. While the US Special Forces met some resistance, they reported no fatalities.

The consequences are likely to reshape Venezuelan-Cuban relations, including the still-vital oil shipments. “If Venezuela’s relations with the United States are reconfigured, Venezuela’s relationship with Cuba could become a bargaining chip,” says Pavel Vidal, a Cuban economist at the Pontifical Xavierian University in Colombia. “Without Venezuela as an ally, the country risks being left in a kind of geopolitical vacuum, much more isolated financially, with unimaginable social consequences.”

In return for fuel, Havana for decades sent medical brigades to Venezuela, as well as military and intelligence officers who had honed their craft over decades of spying on their own people. If, as Mr Trump says, he plans to “run” Venezuela during a transition period (though it is by no means clear what he means by “running” Venezuela), Mr Maduro’s replacement, the acting president Delcy Rodríguez (who is due to be sworn in on January 5th), may well have to send the remaining Cuban military advisers packing. Despite their failure to protect Mr Maduro, they may be missed, leaving Ms Rodríguez more exposed to domestic in-fighting and to Mr Trump’s threats of a fate “worse than Maduro” if she does not co-operate.

Cuba’s main concern is oil. Ms Rodríguez is also Venezuela’s energy minister. Although she is ostensibly ideologically aligned with Cuba, diplomats say she was running out of patience with Cuba’s lack of gratitude—and inability to pay—for its cheap fuel. If Venezuela cuts off its supply of oil to Cuba, “it is difficult to imagine a foreign ally filling that void,” said Ricardo Torres, a Cuban-born economist at American University in Washington.

“I imagine the [Cuban] Communist party is extremely worried,” says Scott Hamilton, deputy head of the United States embassy in Havana from 2015 to 2018. Cuba also receives oil from Mexico and Russia. But with Venezuela under Mr Trump’s thumb, “the apparent quarantine surrounding Venezuela and likely pressure on Mexico suggests that Cuba may have finally run out of oil and fairy godfathers,” added Mr Hamilton.

Neither Russia nor Iran seems likely to fill the oil gap. Russia, though, is probably Cuba’s best hope for a lifeline more generally. The two countries have been stepping up military and economic co-operation in recent years; they have signed defence agreements and Russian warships have docked in Havana. In 2024, two years after Russia invaded Ukraine, Cuba’s president, Miguel Díaz-Canel, wished Russia “success in carrying out the special military operation”. The pair have signed trade agreements, and Russian investment in oil extraction and agriculture in Cuba has expanded. Russia’s entanglement with Cuba, more than anything else, might keep Mr Trump at bay. That, presumably, is what the regime now hopes.

Despite all Cuba’s woes, and Mr Trump’s menacing new aspect, expectations among its exile population in Miami are dampened by six decades of disappointment. “Sure, Cuba is in crisis,” says Yenier Romero, a 42-year-old barber who left the island in 2022, as he snips clients’ hair in Miami’s Little Havana district. “But all they ever taught us was how to survive on nothing.”

But hope, it seems, never died. “Here we swim in this very thick soup of nostalgia,” said Joe Garcia, a Miami-born Cuban-American former member of the United States Congress. “We carry the idea of some kind of justice in the end, that communism didn’t triumph, that we never gave up the fight, that people are still trying to figure out a way to bring freedom back to Cuba.” ■