The U.S.–Cuba Had a Deal — But Trump Tore It Apart

March 10, 2026

This March marks 10 years since Barack Obama landed in Havana and opened a new era in U.S.-Cuba relations. Then came Donald Trump — and he didn't just walk away from the table, he flipped it over.

Peter Kornbluh, Director of the Cuba Documentation Project at the National Security Archive, breaks down how the most significant diplomatic breakthrough in decades was deliberately dismantled by the Trump administration — and how millions of Cubans have felt the consequences through blackouts, shortages and mass migration.

Now, in his second term, Trump has unleashed a new wave of sanctions and economic pressure against the island, leaving Cuba in its worst crisis in decades and pushing U.S.-Cuba relations back to Cold War lows. 

Kornbluh examines what was lost, who is paying the price and whether any path forward still exists.

TRANSCRIPT

“Donald Trump, in so many ways, is just not your typical political figure, and his ability to understand and act politically in the best interests of the United States of America are compromised by his desire to act in his own best interests, which usually are transactional and financial,” said Peter Kornbluh, U.S.–Cuba relations expert and director of the Cuba Documentation Project at the National Security Archive.

“You have Marco Rubio as Secretary of State,” Kornbluh added.

“You have one of the leading voices for regime change in Cuba now controlling the levers of U.S. foreign policy power,” he said. “[He] tries to just twist and press and squeeze and wreak havoc in Cuba.”

“The more the United States tries to destabilize Cuba, the more Cubans are going to leave,” Kornbluh explained.

“For me, it's really difficult to think, even imagine that there are Cubans who are trying to make the life of other Cubans more difficult,” said Liz Oliva Fernández, journalist with Belly of the Beast.

“I haven't seen other migrant groups in the United States with such strong feelings,” she added. “What is your perspective on that?”

“There is a true humanitarian crisis in Cuba,” Kornbluh responded.

“And it's just cruel and malicious for the Trump administration to not respond to that crisis, simply on humanitarian grounds,” he said.

“I do hope that, you know, other countries step up,” Kornbluh added.

“In the past, just to bring history into it, Henry Kissinger himself heard a lot of complaints about U.S. policy towards Cuba in the mid 1970s,” he explained.

“And he eventually decided that he should respond to those complaints by reaching out to Fidel Castro to try and normalize relations,” Kornbluh said.

“He decided that, pragmatically speaking, U.S. interests would be served by normal, peaceful coexistence with Cuba,” he added.

“Every president since Eisenhower engaged in some form of secret dialogue with the Cubans to try and improve, if not overall relations, specific parts of our bilateral relationship,” Kornbluh explained.

“And it's not out of the question that the Trump administration could also pursue some type of dialogue on very specific elements, whether it's counter narcotics or migration, which is the most obvious one,” he said.

“Did Obama's announcement of new relations with Cuba in 2014 surprise you?” Oliva asked.

“It was so incredible. It was just about everything that we had worked for,” Kornbluh recalled.

“The United States deciding it was going to acknowledge the failure of its policy of aggression towards Cuba over the last half century and adopt an approach of positive engagement, of coexistence with the Cuban revolution in a way that would advance both U.S. interests, security interests, humanitarian interests, economic interests, political interests, regional interests, as well as the interests of the Cuban people,” he explained.

“I was actually in Cuba that day at a conference on U.S.-Cuban relations,” Kornbluh said.

“Raúl Castro and Barack Obama were on television at the same time, saying we have come to an agreement that we're going to normalize diplomatic relations,” he added.

“There's more to be done. The embargo has to be lifted,” Kornbluh noted.

“And then Barack Obama basically saying we're going to start a new chapter in U.S.-Cuban relations,” he said.

“Since you were in Havana, could you describe to me a little bit more how the environment was in Havana that day?” Oliva asked.

“It was incredible. I can't describe it to you,” Kornbluh said.

“The car horns started to honk in the streets. People poured into the streets,” he recalled.

“And I remember getting into a taxi in front of the Hotel Nacional and the taxi driver saying: ‘Gosh, you know, this is so great. I'm finally going to get a Ford van,’” Kornbluh said.

“There was such a euphoria at that moment. And the future seemed so very promising,” he added.

“A lot of changes took place very quickly,” Kornbluh explained.

“Obama normalized U.S. travel to Cuba,” he said.

“American Airlines, Delta, Southwest, JetBlue, to actually fly to Cuba for the first time,” Kornbluh continued.

“Hundreds of thousands of U.S. citizens flocked to Cuba,” he said.

“And they came to Cuba to see for themselves what Cuba's realities were,” Kornbluh explained.

“But as more and more of them came, the Cuban economy responded and the private sector expanded and Obama authorized companies like Airbnb to go into Cuba,” he added.

“At one point, Cuba was Airbnb's fastest growing market,” Kornbluh noted.

“It really was a win-win situation for both sides,” he said.

“A common narrative among hardliners about the Obama opening is that nothing good came of it and even made things worse for Cubans,” Oliva said.

“They allege there was an increase in human rights abuses. Is that accurate?” she asked.

“Countries that are under the threat of aggression from other countries tend to be far more rigid and far more repressive,” Kornbluh responded.

“And so the less of the threat of the United States, the more open,” he said.

“It was an evolution of change that simply the restoration of normal political, economic, cultural and security relations brought between the United States and Cuba,” Kornbluh explained.

“How was Obama's secret negotiations process with the Cuban government different from previous administrations?” Oliva asked.

“President Obama really did want to change the relationship,” Kornbluh said.

“He didn't really demand any specific actions on Cuba's part, any concessions as some of his predecessors had during secret negotiations with Fidel,” he explained.

“He took unilateral actions to improve relations,” Kornbluh added.

“His negotiators treated the Cuban negotiators with the utmost personal respect,” he said.

“And so there was a new tone from President Obama in the U.S. approach to Cuba,” Kornbluh noted.

“And there was clearly an effort to advance the cause of normalization, to make normalization, as Obama officials put it, irreversible,” he said.

“But it wasn't. When Obama left office, did you realize that the normalization was as fragile as it turned out to be?” Oliva asked.

“You know, there was a will at that point and there was a way at that point,” Kornbluh responded.

“The amount of effort and the courage it took for President Obama to actually go to Cuba and spend two days there and bring an entourage of cultural figures, business figures, political figures and others, senators, congressmen, etc., in an attempt to create a momentum and a very, very positive energy for going forward,” he explained.

“He also started to authorize pretty significant U.S. companies to do business in Cuba,” Kornbluh said.

“But on the Cuban side, there was a reluctance to see U.S. corporations return to Cuba and invest in Cuba,” he added.

“The time was very short. It was only really two years left of Obama,” Kornbluh noted.

“Donald Trump hated everything that Obama had done,” he said.

“And Trump, just for spite, set out to reverse methodically everything Obama had done,” Kornbluh added.

“He basically let Marco Rubio start to direct the show, to control an aggressive U.S. policy towards Cuba,” he said.

“He not only stopped Obama's process of normalization, he fully reversed it and put forth a slew, a new generation of punitive sanctions,” Kornbluh explained.

“There was over 200 new punitive regulations and restrictions that hampered Cuba's ability to import oil, to transport goods to Cuba,” he said.

“They put Cuba back on the terrorism list falsely, maliciously, malevolently,” Kornbluh added.

“He cut off the ability of Cuban Americans to send remittances to their loved ones in the middle of the pandemic,” he said.

“And Trump did this on the argument that somehow the Cuban state and the Cuban military were gaining funds out of these remittances,” Kornbluh explained.

“Every company that does financial transactions around the world take a small percentage for exchanges. That's just the way international commerce works,” he said.

“And what about Biden? Is there some difference between the first Trump administration and Biden's?” Oliva asked.

“Well, I feel there certainly was a difference,” Kornbluh said.

“There was a difference in tone, but there was no real initiative to improve the situation,” he explained.

“President Biden and his administration did not really step forward and change the policy back to that significant positive engagement,” Kornbluh said.

“And yet, for whatever political reasons, they did not take significant steps to return to that policy and try to use their four years to consolidate better relations with Cuba,” he added.

“So now you have a situation where Trump doesn't have to do a lot more to continue to turn the screws on Cuba,” Kornbluh said.

“The real issue here is the incredible contrast between the success and the promise of 10 years ago and the dire catastrophic situation and the prospect of further deterioration in U.S.-Cuban relations today,” he concluded.

“Do you think Cuba matters, U.S.-Cuban relations matters for the rest of the world, Europe, for example?” Oliva asked.

“There are a number of other countries who have interests in Cuba, but many countries have interest in stability in Cuba and Latin America,” Kornbluh said.

“And the United States has a real interest in stability in Cuba and Latin America,” he explained.

“We have geopolitical interests. We have humanitarian interests,” Kornbluh added.

“We have interests because we would like to see less migration from Latin America to the United States,” he said.

“Those are all issues that can be helped by a positive policy towards Cuba rather than a punitive policy towards Cuba,” Kornbluh concluded.