President Obama's 2014 easing of U.S. policy toward Cuba helped funnel American travel dollars into military-linked tourism conglomerates even as state security agents waged a fierce crackdown on dissent.
The rapprochement also poured hundreds of millions of dollars in U.S. spending into privately owned businesses on the island, supercharging the growth of an entrepreneurial middle class independent of the communist state. It opened a new market for American corporations, with JetBlue and American Airlines operating from gleaming new Havana offices and tens of thousands of private bed-and-breakfasts listed on Airbnb.
Internet access became an affordable reality for hundreds of thousands of Cubans as President Raul Castro met a pledge to Obama and opened nearly 400 public Wi-Fi access points across the country. Longtime enemies separated by 90 miles of ocean struck agreements to cooperate on issues ranging from human trafficking to oil spills.
This is the complex scenario facing President Trump as Cuban American legislators and lobbyists pressure him to fulfill his campaign promise to undo Obama's deal with Cuba. The administration is close to announcing a new policy that would prohibit business with the Cuban military while maintaining the full diplomatic relations restored by Obama, according to a Trump administration official and a person involved in the ongoing policy review.
"As the president has said, the current Cuba policy is a bad deal. It does not do enough to support human rights in Cuba," White House spokesman Michael Short said. "We anticipate an announcement in the coming weeks."
Still under debate: new restrictions on American leisure travel to Cuba, which has more than tripled since Obama's announcement, to nearly 300,000 last year.
Anti-Castro Cuban Americans hate the idea of U.S. travelers enjoying mojitos in the police state that drove exiles from their homes and businesses. Tourism to Cuba remains barred by U.S. law, and American travelers to Cuba still must fall into one of 12 categories of justification for their travel, including religious and educational activities meant to bring the traveler into contact with Cuban people.
When Obama took office, "people-to-people" travelers could see the country only as part of organized tours — a measure meant to guarantee that Americans experienced educational activities such as visits to printing workshops or organic farmers markets.
In reality, the tour requirement guaranteed that American travelers spent virtually every second of their time in Cuba under the direct control of the government, which requires U.S. tour operators to use government tour buses and guides and stay almost entirely in state-run hotels.
As his second term came to a close, Obama eliminated that requirement and opened the door for tens of thousands of travelers to book their own independent trips to Cuba.
Opponents of Obama's rollback say that has allowed many to engage in prohibited tourism, spending leisure days at the beach and all-inclusive resorts.
But individual travel has also served as rocket fuel for Cuba's burgeoning private sector. Tens of thousands of Americans are booking direct flights on U.S. airlines to Havana, reserving private lodging through Airbnb and spending thousands of dollars on private guides, taxis and restaurants.
A former industrial engineer, 31-year-old Adyarin Ruiz runs a four-bedroom bed-and-breakfast in a restored section of Old Havana that's seeing an increasing number of Americans willing to pay up to $100 a night in a country where state salaries average $25 a month.
"Over the last two years, since relations with the U.S. were restored, I've seen the growth in American tourism, and even more so since the direct flights started," Ruiz said. "The Americans who've come here are VIPS. You can see that they have money and they appreciate and demand quality, and demand that the house looks really pretty."
There are also now U.S. jobs dependent on travel to Cuba. The American pro-detente group Engage Cuba released a study Thursday asserting that a complete rollback of Obama's Cuba policy would cost airlines and cruise lines $3.5 billion over the next four years and lead to the loss of 10,154 travel jobs.
Administration officials who spoke on condition of anonymity in order to discuss ongoing policy talks say domestic political concerns are the main force driving any rollback on Cuba.
During the transition, Trump and Secretary of State Rex Tillerson privately expressed support for Obama's Cuba policy, U.S. officials from the former and current administrations told the Associated Press.
The main people still seeking a reversal in the opening are Sen. Marco Rubio and Rep. Mario Diaz-Balart, both Cuban Americans and Republicans from Florida. The Trump government wants to maintain good relations with Rubio, who sits on the Senate committee investigating Trump's relations with Russia, and Diaz-Balart, a member of the powerful House Appropriations Committee.
Some top Trump advisors also believe that a 2020 reelection victory will rest on keeping the loyalty of Cuban Americans in Florida, whom they see as essential to winning the crucial swing state.
Many object to the Cuban government seeing any benefit from relations with the U.S., and are opposed to thousands of American travelers staying in hotels run by GAESA, an increasingly powerful business conglomerate with deep military ties. Cuban Americans have been particularly offended by Obama allowing U.S. companies to deal directly with military-linked companies, most prominently in an agreement for Stamford, Conn.-based Starwood to manage at least two Havana hotels. Anti-Castro forces have also been demanding action on human rights: Arrests and short-term detentions of protesters climbed from 8,899 in 2014 to 9,940 last year.
Cuban officials say many of those arrests are deliberately provoked by dissidents who are funded and backed by anti-Castro groups with the deliberate objective of driving up detention statistics.
But the officials say there's another reason to tighten America's Cuba policy: pressuring Venezuela. The Trump administration has been looking for ways to force Venezuela to address the near-daily protests and violence trying to shake President Nicolas Maduro's iron grip on power. Cuba is Maduro's close ally and supporter, and measures against the Cuban military would send at least the appearance that the U.S. is taking action.
Meanwhile, Cuba is preparing for its own transition. Castro is planning to leave Cuba's presidency in February and is expected to hand the role to a 57-year-old vice president who has said little about his vision for the country.
Rubio's office described the senator's goals as laying the groundwork for a new generation of Cuban leaders to empower ordinary citizens of the island.