What Does Trump Mean When He Says He Wants a Deal With Cuba?

January 24, 2026

Donald Trump is threatening Cuba: “Make a deal or else…” But in December 2014, the Cuban government already made a deal with another U.S. president, Barack Obama. Obama loosened sanctions and the two countries started normalizing relations. U.S. companies and movie stars flocked to Havana. 

Even Donald Trump thought the opening was a good idea. That was no shocker. Back then, Trump and Marco Rubio weren't exactly friends. 

So what changed? Trump made a deal. Not with Cuba, but with Rubio.

Belly of the Beast journalist Liz Oliva Fernández looks at how Trump reversed course once in office, and how U.S. politics, driven by Marco Rubio, reshaped Cuba policy. 

TRANSCRIPT

“Donald Trump is threatening Cuba, saying ‘make a deal or else,’” explained Liz Oliva Fernández, journalist with Belly of the Beast.

“What kind of deal are you looking for from Cuba?” asked a reporter. “What kind of deal are you looking for from Cuba?”

“You’re gonna find out pretty soon,” replied Donald Trump, President of the United States.

“Wait, what?” Oliva reacted. “Is he talking about a deal like this one?”

“Today, the United States of America is changing its relationship with the people of Cuba in the most significant change in our policy in more than 50 years,” said Barack Obama, then President of the United States. “We will end an outdated approach that for decades has failed to advance our interests.”

“In December 2014, Barack Obama made a deal with Cuba,” Oliva explained. “He started normalizing relations and loosening sanctions, and U.S. companies and visitors flooded Havana.”

“Havana was overcrowded,” recalled Idania del Río, Cuban entrepreneur. “Celebrities, musicians, politicians, everybody. It was insane. Chanel runway, Fast and the Furious shooting, Rolling Stones concert. The mood was that anything was possible.”

“Even Donald Trump thought the opening with Cuba was a good idea,” Oliva noted.

“I don’t agree with President Obama,” Trump said in 2015. “I do agree that something should take place after 50 years. It’s enough time, folks.”

“That was no shocker,” Oliva explained. “Trump had been trying to do business in Cuba for years.”

“In 2008, Trump registered his brand at the Cuban Office of Industrial Property,” she continued. “It’s where foreign companies apply to do business in Cuba.”

“Then in 2015, Trump’s executives came to Cuba to smoke cigars, play golf, and scope out investment opportunities,” she added.

“That was at a time when Trump and Marco Rubio were not exactly friends,” Oliva recalled.

“We have a con artist as the front runner in the Republican Party,” Trump said during the campaign. “Thank God he has really large ears, the biggest ears I’ve ever seen. And you know what they say about men with small hands. Rubio, total lightweight.”

“Then Trump made a deal,” Oliva explained. “Not with Cuba, but with Rubio.”

“I am canceling the previous administration’s completely one-sided deal with Cuba,” Trump declared after taking office.

“Rubio gave Trump his support in Florida and the Senate,” Oliva said. “Trump gave Rubio Cuba policy.”

“Trump’s Cuba policy was directly designed by me, and it’s still in effect,” stated Marco Rubio, U.S. Senator.

“Trump says Cuba’s economy is a disaster,” Oliva noted. “And it is.”

“Cuba’s in bad shape,” Trump said. “They’re doing very poorly. Really third world all the way.”

“But it’s a disaster that he helped to create,” Oliva added.

“Trump’s not just gaslighting Cuba,” she continued. “He’s doing it to Venezuela too.”

“We are the largest American oilfield services company,” said Jeff Miller, CEO of Halliburton. “We’ve been in Venezuela a long time, and I just couldn’t express more gratitude for the opportunity to return.”

“When did you leave? When did you leave Venezuela?” Trump asked.

“As a company, we left under the sanctions in 2019,” Miller explained. “We had intended to stay, but when the sanctions went into place, we were required to leave.”

“So let’s get this straight,” Oliva said. “Trump destroys Venezuela’s economy, then blames them for it, and tells them they have to open the doors to U.S. companies that he himself kicked out in the first place.”

“I mean, the irony,” she added.

“Now Trump says he wants a deal with Cuba too,” Oliva continued.

“In Venezuela, Trump seemed happy to leave the government in place, without Maduro,” she explained. “But in Cuba, he might be looking for more than that.”

“One of the things I want taken care of are the people that came from Cuba, that were forced out or left under duress,” Trump said. “They’re great citizens of the United States right now.”

“Trump is not talking to Cubans who live in Cuba,” Oliva explained. “And he’s not talking about Marco Rubio.”

“Rubio has never stepped foot in Cuba,” she added. “His parents left Cuba years before the Revolution. They fled the U.S.-backed Batista dictatorship, not communism.”

“Trump is talking about the Cuban Americans behind Marco Rubio,” Oliva concluded. “The powerful families in Florida who think Cuba still belongs to them.”

“Wealthy Cubans in this country donate heavily to senators and congressmen who will maintain the embargo,” explained Ramón Díaz, Cuban-American businessman. “The more the embargo failed, the more resentful and hateful some Cubans became, and that fueled the money that kept these politicians in power.”

“The United States has never had a problem playing judge and executioner in Latin America,” Oliva said. “Trump may be more open about it, but he’s not the exception. He’s the rule.”

“But Cuba has refused to bow to U.S. aggression,” she continued. “It has resisted a U.S.-funded invasion, acts of sabotage, and the longest-running sanctions in modern history.”

“Rubio and Trump may want to recolonize Cuba,” Oliva concluded, “but history suggests that such ambitions have never been easily imposed on the island.”