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What’s the deal between Donald Trump and Cuba?

US is reportedly seeking to negotiate regime change in Cuba, but the country has no oil and exports little

Drivers wait in line to refuel in Havana, Cuba, on January 28th, 2026. Photograph: YAMIL LAGE/AFP via Getty Images
Drivers wait in line to refuel in Havana, Cuba, on January 28th, 2026. Photograph: YAMIL LAGE/AFP via Getty Images

Donald Trump has been sabre-rattling about Iran this week, warning the government there that it is running out of time to make a deal with him. He also has his sights on Cuba.

Tightening the screw

Immediately after the abduction by United States special forces of Venezuela’s president Nicolás Maduro and his wife Celia Flores on January 3rd, attention turned to Cuba as Donald Trump’s next likely target in the region. Secretary of state Marco Rubio said hours after the operation that if he was in the government in Havana, he would be worried, and a week later, Trump told the island what to expect.

“THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA - ZERO!” he posted on Truth Social.

“I strongly suggest they make a deal, BEFORE IT IS TOO LATE”

Cuba has relied on subsidised oil from Venezuela to keep the lights on since Hugo Chavez came to power in Caracas in 1999 but Washington now determines where Venezuelan oil goes. Mexico said this week that it had temporarily stopped oil shipments to Cuba, a move president Claudia Sheinbaum insisted was “a sovereign decision” that was not made under pressure from the US.

Bloomberg reported this month that European diplomats in Havana fear the energy shortage could close Cuba’s ports and spark a catastrophic food shortage. Trump appeared to welcome this deterioration when he spoke to reporters on Tuesday.

“Cuba will be failing pretty soon. Cuba is really a nation that’s very close to failing,” he said.

“You know, they got their money from Venezuela. They got the oil from Venezuela. They are not getting that anymore.”

Trump’s approach is consistent with US policy towards Cuba since 1960, a year after Fidel Castro’s revolution overthrew Washington-backed dictator Fulgencio Batista, when Lester Mallory, deputy assistant secretary of state for Inter-American affairs, wrote a memo calling for economic sanctions on the island. Mallory said that since most Cubans supported Castro, the only way to change public opinion was to generate disenchantment and disaffection based on economic hardship.

“It follows that every possible means should be undertaken promptly to weaken the economic life of Cuba. If such a policy is adopted, it should be the result of a positive decision which would call forth a line of action which while as adroit and inconspicuous as possible makes the greatest inroads in denying money and supplies to Cuba to decrease monetary and real wages to bring about hunger, desperation and overthrow of government,” he wrote.

The Wall Street Journal reported last week that the Trump administration is looking for people inside the government in Havana to negotiate a deal to end the Communist Party’s rule. The US believes that Cuba’s economy is close to collapse, with chronic shortages of basic goods and medicines and frequent blackouts.

What remains unclear is what kind of deal Trump wants from Cuba, which unlike Venezuela has no oil and exports little else. The US president displays no emotional attachment to democracy at home or abroad and there is in any case no significant, organised political opposition to the Communist Party in Cuba.

Although Cuba is small, poor and weak, there is one lever it has deployed against the US several times over the years: mass migration. At various points in the 1960s, the 1980s and the 1990s, the Cuban authorities facilitated large numbers of its citizens who wanted to emigrate to the US, sometimes on makeshift rafts.

Cuban immigrants traditionally received special treatment from the US authorities but the Trump administration has made legal immigration almost impossible and has started deporting Cubans. A chaotic collapse of the government in Havana could trigger a surge of migration to the US, which is just 145km from the coast of Florida.

As Trump tightens the screw on the Cuban government and its people, he should perhaps be careful what he wishes for.

Please let me know what you think and send your comments, thoughts or suggestions for topics you would like to see covered to denis.globalbriefing@irishtimes.com

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