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After Fidel Castro, How Will Trump Approach Cuba?

President-elect has promised to roll back Obama administration's actions without a better deal

President-elect Donald Trump, left, talks after a meeting with U.S. President Barack Obama, right, in the Oval Office on Thursday. (Win McNamee/Getty Images)
President-elect Donald Trump, left, talks after a meeting with U.S. President Barack Obama, right, in the Oval Office on Thursday. (Win McNamee/Getty Images)

While President Barack Obama offered prayers for the people of Cuba and condolences for the family of deceased Cuban President Fidel Castro, President-elect Donald Trump called out the decades-long repression of the authoritarian regime.

“Fidel Castro’s legacy is one of firing squads, theft, unimaginable suffering, poverty and the denial of fundamental human rights,” Trump said in a statement Saturday. “While Cuba remains a totalitarian island, it is my hope that today marks a move away from the horrors endured for too long, and toward a future in which the wonderful Cuban people finally live in the freedom they so richly deserve.”

Those differing approaches might provide insight into the potential for Trump to shift back toward a harder line U.S. policy regarding the island. The Obama administration has worked to ease the trade embargo against the Communist country and negotiated with Fidel Castro’s successor as president, his brother Raul Castro.

In his statement reacting to Fidel Castro’s death Friday night at age 90, Obama said, “During my presidency, we have worked hard to put the past behind us, pursuing a future in which the relationship between our two countries is defined not by our differences but by the many things that we share as neighbors and friends – bonds of family, culture, commerce, and common humanity. This engagement includes the contributions of Cuban Americans, who have done so much for our country and who care deeply about their loved ones in Cuba.”

Campaigning in Miami in September, Trump argued that Obama had cut a bad deal with the Cuban regime. But it was not clear whether that would mean Trump would seek to reimpose restrictions, such as seeking to stop commercial flights between Cuba and the continental United States that have already won regulatory approval.

“All of the concessions that Barack Obama has granted the Castro regime were done with executive order, which means the next president can reverse them. And that is what I will do unless the Castro regime meets our demands,” Trump said on Sept. 16. “Those demands will include religious and political freedom for the Cuban people and the freeing of political prisoners.”

The last phrase of that part of the speech appeared to be an ad-lib, as it did not appear in the prepared remarks distributed to the media, a nuance that CNN caught at the time.

In a sign of what might be to come, Trump has appointed one of the foremost critics of the Obama administration’s effort to open up the relationship between the United States and Cuba to help oversee the transition at the Treasury Department.

“In short, Obama’s new course for Cuba has made a bad situation worse,” Mauricio Claver-Carone wrote in an opinion piece for the Miami Herald earlier in November. Claver-Carone is the executive director of Cuba Democracy Advocates, which has supported the embargo.

“There’s no longer any rational strategy behind President Obama’s ‘Cuba policy.’ It has gone from what it initially portrayed as a noble purpose to pure sycophancy in pursuit of ‘historic firsts.’ Unfortunately, those Cuban dissidents who recognized Obama’s intent from the beginning and labeled it ‘a betrayal’ of their fight for freedom have now been proven correct,” Claver-Carone wrote. “Their foresight has come at a terrible cost.”

Two weeks after Trump spoke to U.S.-Cuba relations in Miami, Newsweek reported on documents that appeared to show an effort by Trump’s hotel and casino business to explore opportunities in Cuba should the embargo be eased, potentially running afoul of the embargo by having consultants travel to the island.

The presidential campaign of Democratic nominee Hillary Clinton had sought to gain traction in the very anti-Castro Cuban-American community in South Florida by running radio ads highlighting the Newsweek report in early October.

Sen. Marco Rubio, R-Florida, responded to Castro’s death by calling on Trump and leaders on Capitol Hill to do more to support the pro-democracy cause in Cuba.

“The future of Cuba ultimately remains in the hands of the Cuban people, and now more than ever Congress and the new administration must stand with them against their brutal rulers and support their struggle for freedom and basic human rights,” Rubio said in a statement.

House Minority Leader Nancy Pelosi said that the Obama administration has taken “historic steps” toward a new relationship between the U.S. and Cuba and “We are hopeful this progress will continue under the new Administration.” 

“Still, we meet this day with clear eyes,” she said in a statement. “Generations of Cuban political prisoners, democracy activists and families suffered under Fidel Castro’s rule.  In their name, we will continue to press the Cuban regime to embrace the political, social, and economic dreams of the Cuban people.”

Senate Foreign Relations Chairman Bob Corker was at least initially striking an optimistic tone about what Castro’s death could mean for the people of Cuba.

“Under Fidel Castro’s brutal and oppressive dictatorship, the Cuban people have suffered politically and economically for decades, and it is my hope that his passing might turn the page toward a better way of life for the many who have dreamed of a brighter future for their country,” the Tennessee Republican said Saturday.

Senate Majority Leader Mitch McConnell, R-Kentucky, largely echoed Corker.

“While Fidel Castro is gone, sadly the oppression that was the hallmark of his era is not,” McConnell said. “It is my hope that the Cuban regime will use this opportunity to turn the page for the good of the Cuban people and for all those living in the Americas. Freedom and democracy are long overdue in Cuba.”

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