How Trump could roll back Obama’s Cuba policies — and why he might not want to

The death of Cuban revolutionary and former dictator Fidel Castro marked the symbolic end of an era, but it’s the impending end of the Obama era — and the start of the Trump one — that could have the far bigger impact on Washington’s fragile relationship with Havana.

On Tuesday, Reuters reported that President Obama would not be sending a “U.S. delegation” to Cuba to attend Castro’s funeral; this was followed minutes later by a report that US would, however, “be represented at Castro funeral by Security Adviser [Ben] Rhodes and U.S. Ambassador to Cuba [Jeffrey] Delaurentis.”

That the leader of the United States would choose not to formally honor the death of one of the country’s most indomitable foes is no surprise, of course. But that President Obama is still sending a delegation-in-all-but-name is notable.

Toward the end of his tenure, President Obama pursued a dramatic thawing of relations between the two Cold War enemies. Using his executive authority, Obama relaxed some of the trade and travel restrictions in the longstanding US economic embargo on the country, and, last July, the US officially restored diplomatic relations with Cuba. This was all part of a broader deal reached between the two countries in 2014 that also involved a prisoner exchange of US and Cuban spies and led to Cuba being taken off the US list of state sponsors of terror.

Now President-elect Donald Trump is threatening to undo all of it. On Monday, Trump tweeted that he would “terminate” the deal unless Cuba agrees to “make a better” one:

Trump has threatened to reverse the restoration of diplomatic relations with Cuba before. At a speech in Miami on September 16, he stated that “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.”

So could Trump really do that? The answer is yes, absolutely. Once he takes office, Trump could literally reverse every single executive action Obama issued on Cuba.

But there’s another, potentially more important question here: Would Trump actually want to terminate the deal?

For all his talk about pushing for more “religious and political freedom for the Cuban people” — the main reasons he cites for opposing the Obama administration’s deal is that it didn’t go far enough in this direction — Trump has so far shown little commitment to promoting such values elsewhere, especially if doing so comes at the expense of US economic interests.

From Afghanistan, where Trump opposes continuing to “waste” money helping to rebuild that country and foster democracy that could instead be spent rebuilding the US, to protecting NATO allies from Russian aggression, which Trump thinks should only be done if those countries cough up more money, Trump consistently puts economic interests ahead of loftier ideals like promoting democracy and human rights.

And since a number of high-profile US businesses have already begun moving into the newly open Cuban tourism market, reimposing strict economic and travel restrictions on the country would most certainly harm US economic interests.

Just how willing would the real estate mogul turned politician, who ran on a platform of restoring American economic power, really be to kill potentially lucrative business opportunities for US companies in the name of freedom?

In December 2014, after 18 months of secret negotiations between high-level officials, President Obama and Cuban President Raúl Castro announced that they had reached a landmark deal.

Under the deal, the Castro government freed US aid worker Alan Gross, who had been imprisoned in Cuba for five years, as well as an unnamed American intelligence operative who had been held for nearly two decades. In return, the White House released three Cuban operatives who had been jailed in the US. The administration also agreed to take Cuba off the State Department’s list of state sponsors of terror.

In addition, President Obama, using his executive authority, would relax a number of economic and trade restrictions related to the 1962 Cuban embargo. US financial institutions would be allowed open accounts with their Cuban counterparts; restrictions on US agricultural and telecommunications equipment to Cuba would be eased; Americans would be permitted to use credit and debit cards while in Cuba and send more money back to relatives in Cuba from the US; and Cubans could buy certain US consumer goods online.

The administration also changed regulations to make it easier for Americans to travel to Cuba, including by restoring regular air travel between the two countries.

But the embargo itself, which requires congressional approval to be rescinded, remains in place to this day.

Announcing his latest executive action further relaxing restrictions on Cuba in October, Obama said his goal was to “make our opening to Cuba irreversible.”

But as Obama knows full well, executive actions themselves can easily be overturned by the next president.

“President Trump could direct the Treasury Department, the Commerce Department, the Department of Transportation, US Customs and Border Protection, the Department of Justice, and the Department of State to rescind, revise, or leave in place any of the decisions that President Obama has taken since December 17, 2014,” says John Kavulich, the president of the US-Cuba Trade and Economic Council.

For instance, Trump could order the State Department to place Cuba back on the list of state sponsors of terror. He could break off diplomatic relations with Cuba and once again shutter the US Embassy in Havana. Both of those actions would be completely within Trump’s legal right to do as president.

What Obama likely meant, though, was that he hoped that by the time someone else came into office, the economic ties between the two countries would have become so entrenched that unraveling them in practice would be so difficult and costly that the next president wouldn’t opt to do so.

Take, for instance, the restoration of direct flights between the US and Cuba. Since it was a non-binding arrangement between the two countries, and not a formal agreement or treaty, Trump could legally back out of the deal when he takes office.

But, Kavulich says, the Trump administration would likely face major pushback — including lawsuits — from the airline industry if Trump were to do that, because airlines have already made substantial financial investments in “good faith” based on the new regulations from the Obama administration.

And that’s just the airlines. A number of tourism and travel companies such as Airbnb, Carnival Cruise Line, and Starwood Hotels have also taken advantage of the Obama administration’s relaxed restrictions to expand into Cuba, hoping to cash in on what they expect will eventually become a booming new tourist hot spot.

So while we know for sure what Trump can legally do once in office, that is not at all the same thing as knowing what he will do once in office.

If you’d only read that one tweet from Trump on Monday morning, you’d be forgiven for thinking Trump is a hard-liner on Cuba. But the reality is that Trump’s position on Cuba, much like his positions on many other issues, has fluctuated over the years, and has at times been influenced by business interests.

In 1999, Trump wrote an op-ed in the Miami Herald in support of the US embargo: “Several large European investment groups have asked me to take the ‘Trump Magic’ to Cuba,” Trump wrote. “My investment in Cuba would directly subsidize the oppression of the Cuban people. ... But I’d rather lose those millions than lose my self-respect.”

But according to documents uncovered by Newsweek’s Kurt Eichenwald, just seven months before Trump wrote that op-ed, he had secretly sent a delegation on behalf of Trump Hotels and Casinos Inc. to explore potential business opportunities in the communist country.

When asked in an interview on September 7, 2015, about the Obama administration’s decision to open up to Cuba after decades of frosty relations, Trump stated, “I think it’s fine. I think it’s fine, but we should have made a better deal. The concept of opening with Cuba — 50 years is enough — the concept of opening with Cuba is fine. I think we should have made a stronger deal.”

Almost exactly one year later, Trump told a crowd in Miami that he would overturn the Obama administration’s policies if the Castro regime didn’t submit to his demands. And this morning, he tweeted the same.

“As a businessman he’s been inconsistent, as a candidate he was inconsistent, as president-elect he’s been inconsistent,” Kavulich says. “However, come January 20, 2017, he may continue to be inconsistent, but he’ll be doing so as the president of the United States of America.”

“Rescinding enhanced travel that Obama has introduced would be the most tragic thing Trump might do, but I don’t think he will,” Robert L. Muse, a lawyer who specializes in US-Cuba trade law, told the New York Times. “He has invested a lifetime in travel, resorts and hotel accommodations, and it’s a global enterprise. It seems counterintuitive.”

But even if Trump does ultimately decide to take a hard-line stance on Cuba, he almost certainly won’t get the response he’s looking for. After all, 50 years of tough US policies toward Cuba failed to achieve the desired political, social, and economic reforms inside the island nation.

As Kavulich notes, “The Cuban government response to anything that President Trump does to it will be, ‘Go f— yourself, bring it on. The revolution was bigger than Fidel, it will last long after Fidel, and we can absorb whatever you want to throw at us.’”