How a Crew of Hardliners Hijacked Donald Trump’s Cuba Policy

Trump is rolling back Barack Obama’s normalization efforts. Here’s how it happened.

Donald Trump visits the Bay of Pigs museum on October 25, 2016.Al Diaz/Miami Herald/ZUMA Wire

On Friday, Donald Trump is scheduled to appear in Miami, home to America’s largest Cuban American community, where he will announce a new rollback of several Obama-era reforms on US-Cuba policy. Trump plans to implement greater restrictions on travel to Cuba and outlaw any business transactions that involve the Cuban military, which is deeply intertwined with most economic activity on the island. The tourism industry will be hit especially hard. “Economic practices that benefit the Cuban military at the expense of the Cuban people will soon be coming to an end #BetterDealforCuba,” Sen. Marco Rubio (R-Fla.), an opponent of the Obama reforms, tweeted on Thursday.

Trump’s announcement is the culmination of a contentious, monthslong process that pitted a small crew of Cuba hardliners within Congress and the administration against virtually the entire US military, intelligence, and diplomatic bureaucracies. (Not to mention many Cuban Americans. In South Florida, majorities say they oppose the 56-year-old embargo and want better relations with Cuba.) The hardliners say Obama’s efforts only empowered and enriched the Castro regime while turning a blind eye to human rights and political abuses. Pro-engagement activists say the current policies are working, bringing money and jobs and opportunity to Cuba. (Trump’s directive is not a wholesale repeal of Obama’s actions. It will not address Obama’s decision to remove Cuba from the state-sponsored terrorism list and to end the “wet foot, dry foot” policy that allowed Cuban migrants who reached the United States to stay here and become permanent residents.)

This is the story of how the hardliners gained the upper hand and—for now—set the administration on a path back to the days of greater hostility toward Cuba.

In February, the Trump administration, led by the National Security Council, began a government-wide review of US-Cuba policy. Such interagency reviews are typical for a new administration. After the different agencies and departments had each assessed their piece of the broader US relationship with Cuba, a so-called deputies meeting was convened in early May. Representatives from the departments of Commerce, Defense, State, Treasury, Agriculture, Homeland Security, and more went around the room offering their perspectives. According to four sources briefed on the meeting, the deputies were almost unanimous in their support for the Cuba policies already on the books, including the Obama-era normalization efforts. While Cuba remains a repressive country that punishes and imprisons critics of the ruling regime, the consensus was that cutting off relations would do little to improve life there.

But there were two strong dissenters in the room, those sources say. The first was from the White House legislative affairs team, which interacts with members of Congress. That staffer, according to the sources, was channeling the opposition of two Florida Republicans who are avowed Castro foes: Rubio and Rep. Mario Diaz-Balart, who represents parts of Miami. The two lawmakers have led the charge to convince Trump to undo the Obama-era reforms.

Rubio and Diaz-Balart had sought to hold Trump accountable to his campaign pledge to renegotiate Obama’s “bad deal” with Cuba, and both men lobbied the president for months to roll back the last administration’s actions. At one point, according to Politico, Rubio urged Trump to take unilateral action. “What you’ve committed to do on Cuba, what you want to do on Cuba, is never going to come from career staff,” Rubio said he told Trump. “It’s going to have to come from the top down. You’re going to have to tell them what to do.” According to the Miami Herald, Rubio gave a nickname to his behind-the-scenes campaign: “Martí,” a reference to the 19th-century Cuban revolutionary and poet José Martí.

Rubio had at least one ally inside the bureaucracy: Mauricio Claver-Carone, who is arguably the most vocal pro-embargo activist and lobbyist in Washington, was working on the inside. A onetime Rubio adviser, Claver-Carone has spent most of his adult life blasting the Castro regime for its human rights abuses and fighting any effort to open diplomatic relations between the United States and Cuba. As the head of the US-Cuba Democracy Political Action Committee, he lobbied to help defeat several measures in 2005 to permit more humanitarian travel to Cuba and allow toothpaste and soap to be included in gift packages sent to the country. He wrote that it was “absolutely unconscionable” for the United States to join forces with Cuba in the disaster relief effort after the 2010 Haiti earthquake. And when a pro-engagement Cuban-American was elected to lead the US-Cuba Business Council in early 2016, Claver-Carone fired off a tweet: “As [Madeleine] Albright would say: There’s special place in hell for Cubans who embrace tyrants that terrorize their own people.”

Shortly before joining the Trump transition team late last year, Claver-Carone condemned Obama’s Cuba reforms in a Miami Herald op-ed as having “made a bad situation worse” by ultimately benefiting the Castro regime, not ordinary Cuban people. So it was an omen of things to come when Trump named Claver-Carone to his transition team. “It tells you something about policy when you take someone at the extreme fringes of an extreme element and put them in a position of responsibility or power,” says Marguerite Jiménez, senior associate for Cuba at the human rights group WOLA.

Since Trump’s inauguration, Claver-Carone has settled in as a senior adviser at the Treasury Department’s office of international affairs. It’s unclear what role he may have played in the Cuba policies being unveiled on Friday. If he was involved in policy decisions regarding Cuba, there is no record that Claver-Carone, who was a registered lobbyist on Cuba issues until November 18, has received an ethics waiver as is required for government staffers working on issues they once lobbied on under the rules laid out by the Trump administration. (Claver-Carone and the Treasury Department did not respond to multiple requests for comment.)

Expecting the agencies to argue in favor of engagement, Rubio’s go-it-alone advice to Trump included urging the president to cancel the NSC deputies meeting in early May, according to a source with knowledge of the request. Trump initially agreed, but H.R. McMaster, Trump’s national security adviser, insisted the meeting go on as planned. (Rubio’s office declined to comment on the call. An NSC spokesman didn’t respond to an email seeking comment.)

Meanwhile, Diaz-Balart used another tactic to lobby the Trump White House. This spring, as the Republican health care bill floundered in the House of Representatives, Diaz-Balart (who, in a Shakespearean twist, is a nephew of the late Fidel Castro) used his position as a key vote in the Obamacare repeal effort to prod Trump to tighten US restrictions on Cuba, according to two sources with knowledge of the discussion. (Diaz-Balart has said it’s a “lie” that he offered his vote in exchange for a Cuba commitment but acknowledged he’s pressured the president to toughen Cuba restrictions.)

The other dissenter at the early May NSC deputies meeting was Carlos Díaz Rosillo, a White House aide to Jared Kushner, Trump’s son-in-law and senior adviser. A former Harvard lecturer and political scientist who worked as a surrogate for the Trump campaign, Díaz Rosillo is not well known in US-Cuba policy circles. One US-Cuba expert I interviewed had to Google his name. Nonetheless, a person who knows Díaz Rosillo, who asked for anonymity to describe private conversations with him, described him as a Cuba hawk. “He’s definitely more of a hardliner,” the person says.

Pro-engagement advocates told me that the NSC deputies meeting was emblematic of the larger schism inside the administration. “There’s a division within the administration between the policymakers and the political advisers,” says Mark Feierstein, a former special assistant to Obama and NSC senior director for Western Hemisphere affairs. “Most policymakers—both within the National Security Council and agencies like State, Treasury, and Commerce—want to maintain the existing policy. That said, Trump has made certain commitments to Senator Rubio and Congressman Diaz-Balart that the White House feels obligated to fulfill.”

What’s different about this moment in US-Cuban relations is that the Cubans have repeatedly indicated that they, like Trump, are ready to negotiate. Cuban President Raúl Castro, brother of the late Fidel Castro, said in January that he hoped for “respectful dialogue” with Trump. This week, CNN quoted a senior Cuban official who said the Castro regime was open to working with Trump. “We know they have a different view of the world,” the official said. “We understand that.”

Vicki Huddleston, the principal officer at the US Interest Section in Havana under President Bill Clinton, the equivalent of the US ambassador to Cuba, says the Cuban leadership’s openness to broker new agreements as well as the restraint it showed by not responding to Trump’s provocations (“Fidel Castro is dead!”) indicated Cuba’s seriousness about new negotiations. “Usually, the Cubans get on their high horse and say terrible things, but they’ve been very mild, very moderate,” Huddleston says. “I think that indicates a certain maturity in Cuba, but I also think it indicates they really would like to continue a good relationship or at least one that provides economic benefits.”

American companies are equally supportive of normalizing relations with Cuba, eyeing a potentially lucrative new market. The US Chamber of Commerce, which is largely aligned with the Republican Party, is a strong proponent of better relations with Cuba. After a recent visit there, Jay Timmons, president and CEO of the National Association of Manufacturers, wrote that “clearly the time is right for positive interactions between the United States and Cuba.” Airbnb expanded to Cuba in 2015, JetBlue began offering direct flights to Havana in November 2016, and servers owned by Google went live on the island this spring.

For now, however, Trump is set to heed the advice of the hardliners—Rubio and Diaz-Balart, Claver-Carone and Díaz Rosillo—and take an oppositional tack with the Cuban government. (A White House official told reporters on Thursday that Rubio was “central” to forming the administration’s new changes.) Trump plans to use the Castro regime’s appalling record on human rights and political freedoms to justify his rollback of US-Cuba policy, but human rights groups including Oxfam, Amnesty International, Human Rights Watch, and WOLA argue that restricting travel, commerce, and intelligence sharing will only make Cuba’s human rights issues worse. “The fact that Obama’s approach hasn’t led to political reform in Cuba after just a few years isn’t reason to return to a policy that proved a costly failure over many decades,” Daniel Wilkinson, managing director for the Americas at Human Rights Watch, said in a recent statement.

If a deal between the United States and Cuba is ultimately what Trump wants, rolling back the past administration’s reforms under the guise of human rights and democracy promotion is the wrong way to do it, says Marguerite Jiménez of WOLA. “There’s no legitimate human rights organization that will go on record and say, ‘Yes, isolation is good for human rights,'” she says. “The rollback will do nothing for human rights on the island.”

Mark Feierstein, the former Obama official, says it was “notable” the extent to which Obama’s policies will remain intact after Trump’s directive goes into effect. “That speaks to the bipartisan recognition of the wisdom of Obama’s approach, and the extent to which the American public, including Cuban Americans, have embraced engagement with the Cuban people,” he says. However, he added, “the reinstated limitations on travel and commerce will hurt, rather than help, the Cuban people.”