President-elect Trump's tough talk on Cuba in the wake of Fidel Castro's death could presage a return to the pre-Obama policy of ignoring the island nation's authoritative government.
Trump has vowed to pursue a "better deal" between the U.S. and Cuba than the one President Obama initiated in December 2014. The president-elect said in late November that he would "terminate" Obama's agreement if Cuba did not meet some of his specific demands.
Proponents of Obama's policy shifts have argued that increased contact with the West could work to erode Raul Castro's power from within, noting decades of embargo did little to bring Cuba closer to freedom.
But critics have accused Obama of moving toward a detente with the Raul Castro regime without pushing for concessions from Cuba, such as greater political freedom for the Cuban people or the return of U.S. fugitives.
Jason Miller, spokesman for Trump's transition team, said shortly after the elder Castro's death that the Trump administration would prioritize the release of political prisoners, the return of American fugitives and gaining more political and religious freedoms for the Cuban people when approaching the incumbent Castro next year.
Those so-called concessions, while always included in U.S. policy goals, were not required of Cuba under Obama.
"Some of them we never really asked for," a Republican congressional aide said of the concessions. "The point of view of a lot of the folks on the Hill was that, if President Obama was going to push for normalization, then obviously the Cuban regime has things that they want and we have certain things that we want, and the belief is that the Obama administration gave the Cubans a lot of what they want and we got nothing in return, even though there were five waves of reg[ulatory] changes."
Those regulatory changes, many of which were issued through the Treasury Department's Office of Foreign Assets Control, eased the process by which individuals could apply for licenses to visit Cuba, and also allowed Americans to buy more personal good while on authorized travel on the island.
One thing Trump could do is return to traditional methods of OFAC licensing, which required would-be travelers to justify their trips to Cuba through a far more rigorous verification process. Tougher enforcement of current laws could also follow under Trump.
However, Renata Keller, an international relations professor at Boston University who studies Cuba, said Obama's openings could prove difficult for the next administration to close.
"In practice, it would be extremely difficult because, yes, they were executive actions, but people have already been making investments based on those executive actions," Keller said.
She pointed to scheduled commercial flights between the U.S. and Cuba and Airbnb rentals as examples of the growing business ties that Trump could struggle to sever.
The White House has also suggested that rescinding Obama's business-friendly overtures to Cuba would be met with resistance due to the "economic impact" such moves would have. But Robert Muse, a Washington-based lawyer with decades of experience in U.S.-Cuba law, said he did not expect to see the few companies that have forayed into Cuba raise strong complaints about another regulatory change.
"One of the oddities of U.S.-Cuba policy has been the lack of a committed, well-funded business initiative relating to Cuba," he said. "It's often been observed that Cuba is just too small a market to warrant it."
At the same time, Muse said the Obama "agreement" Trump has vowed to reverse is not an agreement at all, and wasn't a significant move to change the relationship.
"The word normalization is a misnomer," Muse said. "There wasn't a genuine attempt going on to normalize relations with Cuba."
Instead, Muse said, Obama simply tinkered with regulations within the existing policy framework of encouraging Cuba to change itself, a framework that has yielded no results from a regime that never saw its governance as negotiable.
"He made speeches, but he never fundamentally altered the relationship with Cuba," Muse said of Obama. "He remained stuck in a decades-old policy of trying to promote internal change in Cuba."
Because many of the regulations or executive actions Obama issued were focused on "connectivity" or mutually beneficial "protocols," such as what the two nations would do in the event of a nearby oil spill or plane crash, "you're left with a very, very small area of things that a Trump administration could find objectionable," Muse said.
Chief among them is the "self-directed" travel between the U.S. and Cuba that individuals enjoy much more freely thanks to the Obama openings.
Rather than refreeze relations with Cuba, as Trump has threatened to do, Muse suggested the president-elect could have more success if he pursued a "bold and creative" strategy like the one that led President Nixon to China in search of a no-strings-attached peace with Beijing in 1972 after years of hostility.
Trump's current strategy of requiring concessions in exchange for increased economic and diplomatic contact with Cuba is likely to fail, Muse noted.
"It's not going to work for Trump to try dealing in conditionalities with the Cubans," Muse said. "They don't play that game. They don't see it as a game."