Fresh off the successful US mission to capture Venezuelan strongman Nicolás Maduro earlier this month, US President Donald Trump quickly turned his attention to another Communist-led country in Latin America.
“THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA - ZERO!” Trump posted on his social media platform. “I strongly suggest they make a deal, BEFORE IT IS TOO LATE.”
But what exactly would a deal look like?
The White House is exploring whether Cuban government insiders can help it cut a deal to squeeze out the ruling Communist regime by the end of the year, according to a Wall Street Journal report.
This still leaves an open question of what exactly the United States would want from Cuba if it strikes a deal. Unlike Venezuela, the island nation has much less oil. Its exports are limited – it has even started having to import sugar, a good it was once famed for producing. What about democracy? There is no meaningful opposition in Havana – another contrast with Caracas – complicating efforts to remove the country’s leader, Miguel Díaz-Canel.
“Who do you even do a deal with? Are they going to try to identify someone below the current head of state that they can negotiate with?” Michael Bustamante, a Cuba expert at the University of Miami, questioned during an interview with GZERO. The US and Cuba do have a history of backchannel talks, but it’s less clear what avenue exists between the Trump administration and Díaz-Canel’s team.
While there’s nothing that the US has explicitly stated it wants from Cuba, there is something they’d want to avoid: a rush of Cuban immigrants.
“The Cuban government could unleash a mass migration on US shores as a way to coax Washington to the table for sanctions [relief],” said Bustamante. Havana has used this tactic several times before, he noted, including in the late 1960s when hundreds of thousands took “Freedom Flights” to Miami, in 1980 during the Mariel boatlift – popularized by the film “Scarface” – and again in 1994 in what became known as the “Rafter Crisis.”
There’s been another exodus in recent years, one that eclipses the prior ones by some distance. Over a million people have left, causing the country’s population to drop more than 10% between 2020 and 2024. It wasn’t the Cuban government that induced or facilitated it, though, but rather the COVID-19 pandemic, which wiped out one of the last industries that Cuba could rely on: tourism. The collapse triggered further economic turmoil, pushing many Cubans to seek opportunities abroad. Nicaraguan President Daniel Ortega’s decision in 2021 to drop visa requirements for Cubans helped facilitate this emigration wave, allowing Cubans to migrate to the US without needing a boat.
The Trump administration has aggressively sought to reverse the trend, deporting Cubans in record numbers – a move that has stunned Cuban immigrants, who previously benefited from special treatment by US authorities. It has made the avenue for legal migration from Cuba virtually impossible, restricting access as part of a larger travel ban, ending a family reunification program, and pausing all Cuban immigration applications and asylum claims last month.
Still, the deportation numbers are relatively small: the Trump administration repatriated 1,600 Cubans last year. Yet, from the fiscal years 2022 to 2025, over 675,000 Cubans tried to enter the United States, per the US Customs and Border Patrol.
If someone is pushing Trump to intervene in Cuba in some fashion, it could be Secretary of State Marco Rubio. Even though Rubio’s parents fled Cuba when US-backed leader Fulgencio Batista was in charge in the 1950s, the former Florida senator has made hammering Havana a central part of his political identity – a stance that has long resonated with Cuban Americans, particularly in Florida. Following Maduro’s capture, Rubio also turned his attention to Cuba, telling NBC that the country was “in a lot of trouble.”
“If I lived in Havana and I was in the government,” Rubio said, “I’d be concerned.”
Even with Rubio’s influence on Trump – which appears to be growing – Bustamante doesn’t see how he’d convince the US president to repeat the tactic used in Caracas over in the Caribbean. It would be a “headache” for Trump, he explained.
“It also requires nation building, which is something that this White House remains averse to,” Bustamante added. A former US official, speaking to GZERO on the condition of anonymity, affirmed Bustamante’s belief that an imminent strike on Cuba looks unlikely, suggesting instead that the Trump administration’s tactic will be to let the island collapse of its own accord.
Strike or no strike, can the floundering regime stand? The regime has survived through several periods of economic hardship and mass migration before. The situation was far worse, in fact, following the fall of the Soviet regime in the early 1990s, when the country’s GDP dropped some 30% within four years, per Bustamante. This makes the 11% decline in recent years look mild in comparison.
However, the situation is different now, said Bustamente, because Cuba never really recovered from losing its principal ally.
“The Cuban people have now endured 30-plus years of post-Soviet limbo,” said Bustamante, “and the reserves of legitimacy of the state are about as dried up as one can imagine.”
Still, he doesn’t foresee the regime collapsing.
“I don’t think you get the Cuban government to fall on its own,” said Bustamante. “I think it would take some kind of force majeure.”
