Inside Marco Rubio’s Cuba gamble as Trump pushes a ‘friendly takeover’

• Senator Marco Rubio, once a hardliner on Cuba, is now leading talks with the Cuban government at President Trump's request.
• Discussions have included talks with Raúl Castro's grandson and could involve economic reforms in exchange for lifting some U.S. sanctions.
• Many Cuban Americans in Florida express trust in Rubio to negotiate a deal that could lead to a free Cuba.

MIAMI − For Marco Rubio, disdain of the Cuban government was practically a birthright.

He was raised among Cuban exiles in Florida, and his political ascent from local politician to U.S. senator was propelled by an unwavering hard line toward Fidel Castro and his successors.

But the old guard was out. Donald Trump was on his way back in. And a Cuba deal reached by members of President Joe Biden’s administration – which called for the United States to remove Havana from its list of state sponsors of terror to win the freedom of 553 political prisoners – would rest in Rubio’s hands. 

As members of Biden’s team briefed the incoming secretary of state on the agreement, most expected the zealous Republican to squash the deal as too soft on Cuba’s authoritarian government, according to two people familiar with the meeting. 

Instead, a different Rubio emerged, one who appeared to see the world through the lens of America’s top diplomat rather than a politician winning votes through anti-Castro slogans. He listened carefully with Mike Waltz, the incoming national security adviser. (Cuba was placed back on the list within hours of Trump being sworn in last January.)

Now it’s Rubio himself, the hard-liner who disavowed rapprochement, conducting talks at Trump’s behest as the communist island teeters on the verge of collapse. The discussions with the Castro family have revolved around a possible agreement focused on economic reforms as a way to ease the Cuban peoples’ oppression. Trump’s administration has said the economic pressure Cuba is under will bring about the communist government’s demise.

“Cuba has an economy that doesn’t work and a political and governmental system that can’t fix it. So they have to change dramatically,” Rubio said March 17. “They’ve got some big decisions to make over there.”  

It’s a make-or-break moment for Rubio, 54, who carries the legacy of Cuban exiles who lost everything, fled with nothing and aspire to one day return to a free Havana.

“He’s built his entire political career, his whole political identity, around this one dream of a free Cuba,” said Cesar Conda, the first chief of staff to Rubio in the Senate.

If he facilitates an outcome that leads to less oppression, it would be not only a policy victory, Conda said, but the closing of a circle that has been open for nearly 70 years.

“For him personally, I think it would be everything,” Conda said. “I think it would be the capstone of his political career.”

Rubio has declined to comment on the conversations he has had with the Cubans, which President Miguel Díaz-Canel's regime confirmed for the first time March 13. But they have included talks directly and indirectly with the Castro family, which still wields much of the political power.

"As the President stated, we are talking to Cuba, whose leaders want to make a deal and should make a deal,"  White House Principal Deputy Press Secretary Anna Kelly told USA TODAY in an email.

The president has been nothing short of effusive in his praise for Rubio in the process.

“I think he's going to go down as the greatest secretary of state in history,” Trump told USA TODAY at a news conference March 9. “Look at what we've done as a presidency. Look at what we've done as an administration. They trust Marco, and so do the American people trust. He's been successful no matter where he's been.”

An economic opening would be a roundabout way of getting to the end goal, one close Rubio friend told USA TODAY. It’s neither a full-frontal attack nor a bid to hold people accountable. It’s a compromise position and the only way Rubio sees to set the Cuban people free.

“I think we're seeing that in Venezuela, where he's always fought for a free and democratic Venezuela, but he's settling for an interim strategy,” Conda said.

Inside Rubio's Cuba talks

Rubio boomed into the microphone, blasting Barack Obama’s Cuba deal during the 2016 campaign stop in New Hampshire. 

Obama had removed Cuba from the list of state sponsors of terrorism, reopened the U.S. Embassy, relaxed restrictions on travel, made it easier for American companies to do business with the communist regime and pressed Congress to end the economic embargo against the island nation.

For all the “major concessions,” Rubio said, all Raúl Castro had to do was release dozens of political prisoners.

“What kind of one-sided deal is this?” Rubio said. 

There’s no way the Republican presidential candidate would have accepted the deal if he were calling the shots. “No wonder why people around the world laugh at Barack Obama,” he said.

A decade later, it’s Rubio in the seat of authority.

On a recent trip to St. Kitts, Rubio met with Raúl Guillermo Rodriguez Castro, known as “Raulito,” the former president’s grandson.

Cuba is in dire economic straits, Rubio said at the time.

The administration thought it was close to getting an agreement in March as Trump professed that Cuba wanted to make a deal and hinted that Americans might be able to visit and do business with Havana. 

Discussions have included an off-ramp for Díaz-Canel, the Castro family remaining on the island and deals on ports, energy and tourism. The U.S. government floated dropping some sanctions. 

“It’s widely understood that important calls are still made by Raúl, and so conversations with Raulito as someone proximate to Raúl would seem to make sense as a primary interlocutor for Secretary Rubio,” said Emily Mendrala, deputy assistant secretary of state at the Bureau of Western Hemisphere Affairs working on Cuba during the Biden administration. 

The talks can create a certain assurance that the two sides are moving in the same direction, Mendrala said.

It isn’t clear what the United States would get in return, although sources familiar with the discussions said a deal would hinge on economic reform and could be paired with the release of political prisoners.

If a deal can’t be reached, Trump has hinted at military action: It “may be a friendly takeover, it may not be a friendly takeover." Trump's administration is also said to be weighing indictments for Cuban officials.

But experts and even sources close to the administration who have supported Trump’s foreign adventurism do not think a Venezuela-style military operation like the one that put Delcy Rodriguez in power is what he has in mind.

There’s nothing to invade, one person close to the administration said. It’s more likely that Rubio told Raulito an economic collapse would ruin his party-boy lifestyle. 

Who would run the country from an administrative standpoint if Díaz-Canel were forced out and what that would look like is unknown. But it can succeed, the source close to the administration said, only if the United States maintains its economic leverage. That includes controlling Cuba’s sources of energy and how it accesses capital markets.

A senior U.S. official with knowledge of the strategy said not every country looks the same and acknowledged that the Trump administration is having to deal with those realities. The administration cannot, nor is it looking to, apply one schema to the other, the official indicated.

Florida Sen. Rick Scott said it would be ideal if Díaz-Canel or someone else in the country decided they wanted to be like Rodriguez in Venezuela and work on a peaceful transition.

Scott said he had spoken to Rubio about Cuba and about the Trump administration’s economic pressure campaign. Rubio “wants to make sure there’s not a humanitarian crisis,” Scott said. “I’ve talked to him and he’s focused on this. I hope he’s right.”

From Cuba hawk to dealmaker

At 34, the rising star from West Miami had just been chosen in 2005 by his Republican peers to serve as the next speaker of the Florida House. 

Rubio was the first Cuban American and the only politician from Miami to be selected in more than 30 years.

The ceremony was broadcast via a local anti-Castro radio station into Havana.

“I will always be an heir to two generations of unfulfilled dreams,” Rubio declared in the 2005 speech. “I will always be the son of exiles.”

Rubio had come of age politically in the ‘90s, interning for former U.S. Rep. Ileana Ros-Lehtinen in her Blue Lagoon office, and volunteering on the Hialeah campaign of the late Florida Rep. Lincoln Diaz-Balart. Both were the standard-bearers in Washington. And Rubio absorbed the Cuban exiles’ uncompromising stances. His dream of a free Havana became a driving force.

His own parents left the nation 90 miles off the coast of Florida three years before the 1959 revolution that brought Castro to power. As a child, Rubio told his grandfather he would one day raise an army of exiles to overthrow Castro and become president of a free Cuba. 

As his mentors retired and left political office, Rubio promised to toe the line.

“But their time came and went, and it just didn't happen,” said Nelson Diaz, a longtime friend of Rubio’s and a top aide to him in the state Legislature. “Marco carried the torch in the hopes that he would be able to be, if not be one, but one of the ones to bring about that change.”

Over the course of the next decade, Rubio’s outlook would shift. The geopolitical landscape was changing. So was American politics. 

The Rubio mentors stayed in Congress long enough to see their protégé become a U.S. senator – his first day in Congress was Diaz-Balart’s last − but he was now standing on their shoulders. He wielded influence as chairman of the Senate Foreign Relations Subcommittee on the Western Hemisphere and ran for president, cementing his reputation as an anti-authoritarian hard-liner.

As Trump’s secretary of state, he had the chance to reshape Latin America. 

Trump toppled Maduro in Venezuela and indicated that Díaz-Canel and Cuba could be next. Rubio soon found himself in talks with the grandson of Raúl Castro.

The conversations came as a surprise, given Rubio’s stern criticism of the Castro regime’s human rights abuses and the lack of freedom of expression inside the country. 

Friends of Rubio say his stance and the underlying goal of a free Cuba has never wavered and continue to serve as his personal and political compass.

“Under Trump, it's a different kind of diplomacy,” Diaz said, referring to the talks that Trump has presented as an ultimatum. “It’s a very hard-line diplomacy.”

Back in Washington, lawmakers who sat alongside Rubio on the Senate Foreign Relations Committee affirmed that serious discussions were underway.

“He’s not giving in to them. He’s not giving them resources, he’s not appeasing them. He’s holding them accountable. And I think that’s consistent with what he’s said in the past,” said Scott, now the senior senator from Florida.

In a brief elevator interview, Foreign Relations Chairman James Risch said the talks “are a real thing” and aren’t “make-believe.” The Idaho Republican added, “If anyone can get it done, Marco Rubio can get it done.”

A senior administration official argued Rubio’s own harsh comments about taking out the Castros predated his time working for Trump. The person also said Rubio and Trump have the same overall goal of a free and democratic Cuba.

Asked whether the administration’s policy on Cuba included regime change during testimony before the Foreign Relations panel earlier this year, Rubio told one of his former Senate colleagues, “I think we would love to see the regime there change.”

“That doesn’t mean that we’re going to make it change, but we would love to see it change,” he added. “There's no doubt about the fact that it would be of great benefit to the United States if Cuba was no longer governed by an autocratic regime.”

Havana’s calculus: Cuba’s demands as Rubio takes the lead

A little over a mile and a half north of the White House sits a Colonial Revival mansion that has been the home to the Cuban delegation in Washington for the past century.

When the countries severed relations, it operated under the auspices of other nations, most recently the Swiss. As tensions began to thaw in 2015, Cubans were able to raise their flag at the embassy for the first time since 1961. 

Inside its walls, Cuba’s top diplomat in Washington sat down with USA TODAY March 13 for an interview. 

Havana had been mum on talks with Rubio. But that morning, Díaz-Canel confirmed discussions were underway in a rare TV appearance and signaled changes could lead to Cuba’s biggest economic opening since the communist government seized private property and nationalized all businesses.

“The dialogue with the U.S. is a process,” said Lianys Torres Rivera, Cuba’s top official in the United States. 

Cuba has announced other economic moves such as opening the island up to investment from Cuban Americans, allowing them to own private businesses.

But political change has long been a red line for the Cuban government, which says the U.S. embargo is illegal under international law. Torres Rivera presented the embargo as the very thing inhibiting changes to Cuba’s economic model.

Then Trump shut off Cuba's access to Venezuelan oil after it captured Nicolás Maduro. The island plunged into darkness. Cuba’s humanitarian crisis deepened. The country has a difficult time updating its power grid under the trade embargo, Torres Rivera said, because it costs double or triple the cost to buy the parts that are needed and find a workaround. Hospitals have had to put off non-life-threatening surgeries. Children can’t be vaccinated because there’s no fuel for transportation or refrigeration, Torres Rivera said.

It’s unclear what it would take for the United States to consider ending the long-standing embargo – something of particular interest for the Caribbean nation. (The Trump administration said it would allow U.S. petroleum products, such as diesel, to be sold directly to Cuba’s private sector on Feb. 25, circumventing the regulations.)

Such a move would need help from Congress; the 1996 Helms-Burton Act requires certain conditions be present, including the removal of Fidel and Raul Castro from government, the release of political prisoners, recognition of the freedoms of association and speech, and taking credible steps toward multiparty elections.

Obama and Biden eased some sanctions on Cuba through executive action, and Trump could, too, experts have said. Biden, in his final days in office, removed Cuba’s designation as a state sponsor of terrorism and issued a six-month waiver for Cuba from the embargo.

The Cuban government declined to comment on its opinion of Rubio directly. “We are not talking about exact people, we are talking about dialogue between our governments,” Torres Rivera said.

Rubio told reporters March 17 in the Oval Office the measures Cuba’s government has announced aren’t “dramatic enough” and the country needs “new people in charge.” And while he declined to take a stance on the embargo, he noted it was codified under U.S. law. 

“Suffice it to say that the embargo is tied to political change on the island,” Rubio said after Trump invited him to speak about Cuba.

He has blamed the Cuban government for the suffering of the island’s people in earlier remarks.

In Marco we trust

There’s almost always a line outside Cafe Versailles, an enclave of Cuban Americans on Calle Ocho.

Patrons sip on coladas and cortaditos and munch on croquetas at the iconic walk-up window. They debate the latest baseball matchup and their other favorite pastime: politics. 

Martha Torres says she was born in Cuba and brought to the United States when she was 6 months old. The Miami resident in her early 60s says she would be “all for” a so-called friendly takeover of the Cuban government.

“Whatever it takes to get rid of that government, I support,” Torres said.

That includes talks with the Castros and an economic strategy that allows the people to earn a living wage. “Who better?” she said of Rubio. 

The sentiment is largely shared by the Cuban American population in Rubio’s home state. 

In a poll by Florida International University, 45% of Cuban Americans in South Florida would support a Republican candidate who pursued policies to help independent Cuban businesses; only 35% said the same of Democrats. When the question was broken down by party affiliation, Democrats were significantly more likely to cross party lines, the 2024 survey found. 

Cuban American Mario Cordero, 42, who says he was a journalist and actor in Cuba before he came to America in 2015 with his wife, said he has generally been a skeptic of U.S. efforts to engage Cuba.

But Cordero, who drives for Uber now, said he believes in Trump and Rubio.

"I trust in Rubio. I trust in the administration for that,” he said.

But getting to a deal and making sure the Cuban government sticks to it are two different problems.

Even if Rubio is able to achieve a transitional agreement, the outcome is not guaranteed with the prospect of Congress changing hands after the November elections and a term-limited Trump, American University professor and “Back Channel to Cuba” coauthor William LeoGrande said.

“I think once Donald Trump gets an economic agreement that opens the island to U.S. business, he will have fulfilled his transactional aims in Cuba. I don't think he cares about political transition. He doesn't seem to care about it in Venezuela,” LeoGrande said. “And so I think once there's an economic agreement that's to the advantage of the United States and U.S. businesses, the president will move on to the next thing.”

Conda, on the other hand, said Rubio “won’t stop” until he sees a free Cuba. “And if it takes pragmatic half-steps along the way to get there, I think they can trust that he'll carry it onto the end.”

He recalled sitting with Rubio 13 years ago in the Floridian’s old Russell Senate office puffing Veppos, a brand of electronic cigar.

“He could be smoking a real Cuban cigar in Havana someday soon,” Conda said. “It would be an amazing story.”

Rubio has always been willing to play the long game.

Francesca Chambers is a White House correspondent for USA TODAY covering foreign policy and presidential elections. You can follow her on X @fran_chambers.