President Obama’s historic move to normalize relations with Cuba hasn’t slowed repression by the Castro regime, and the incoming Trump administration is likely to take a tougher stand on restricting tourism, recovering stolen U.S. assets and demanding human rights reforms by Havana, analysts say.

In the two years since Mr. Obama announced a thaw in the United States’ half-century policy of isolating the island nation, the administration has paved the way for increased engagement, approving such measures as daily commercial flights, direct mail service, cruise ship ports of call and the reopenings of long-shuttered embassies in Washington and Havana.

But Mr. Obama’s policy has not been fully embraced on Capitol Hill and is vulnerable to reversal under the Trump administration, though the president’s aides say his detente is already bearing fruit in Cuba and beyond.

“We’re seeing real progress that is making life better for Cubans right now,” said White House Deputy National Security Adviser Ben Rhodes. “Sustaining this policy will allow for further opening, further travel, further U.S. business opportunities.”

But critics say the U.S. money now flowing to Cuba is being pocketed directly by the military and the Cuban intelligence services, not benefiting Cuban entrepreneurs. They also say the government of President Raul Castro has become more repressive since the formal resumption of diplomatic ties with Washington.

“This year, they’ve had over 10,000 politically motivated arrests,” said Ana Quintana, an analyst on Latin America at the conservative Heritage Foundation. “During President Obama’s visit [in March], there were 498 people arrested in those three days.”

Judging by the standards Mr. Obama laid out in December 2014, she said, “the policy has been a failure.”

“It was originally intended to help the Cuban people by providing greater freedoms,” Ms. Quintana said. “It’s been diluted, because they found that they’re not going to get the concessions from the Cuban government that they expected. The vast majority of people who have benefited from this have been the Cuban military and the Cuban government.”

President-elect Donald Trump is likely to take a less rosy view than Mr. Obama of the U.S. engagement with Cuba, say those familiar with his team’s thinking. During the presidential campaign, Mr. Trump criticized Mr. Obama and Democratic rival Hillary Clinton for “turning a blind eye” to Cuba’s human rights violations and denounced Mr. Obama’s initial deal with Havana as a “very weak agreement.” Several anti-Castro Cuban-American conservatives are part of Mr. Trump’s transition team.

Despite making a strong pitch for Florida’s Cuban-American vote, Mr. Trump has kept his options open — aside from pressing harder for human rights.

“All of the concessions that Barack Obama has granted the Castro regime were done through executive order, which means the next president can reverse them — and that is what I will do unless the Castro regime meets our demands,” Mr. Trump said during a Florida campaign swing in September. “Those demands will include religious and political freedom for the Cuban people” — demands that the Castro government has rejected as a condition of the detente negotiations.

In a Twitter post Nov. 28, three weeks after his election, Mr. Trump said, “If Cuba is unwilling to make a better deal for the Cuban people, the Cuban/American people and the U.S. as a whole, I will terminate deal.”

Although Mr. Trump isn’t expected to shut down the revived relationship entirely, he will push harder for U.S. businesses and individuals to recover the estimated $8 billion worth of property expropriated by the Cuban government, said John Kavulich, president of the U.S.-Cuba Trade and Economic Council Inc.

“I don’t see anything expansive [toward Cuba] until there’s movement on the claims,” said Mr. Kavulich, who has been conferring with Mr. Trump’s transition officials. “The Obama administration was suggesting; the Trump administration is going to be requiring.”

Said Ms. Quintana, “Trump is somebody who recognizes that the Cuban government has expropriated about $8 billion of U.S. business assets and U.S. private citizens’ assets. There is no rule of law in Cuba. How can a business exist without property rights?

“You have a military regime that controls everything,” she said. “This is an anti-business environment.”

Targeting tourism

Mr. Trump is also expected to take a sterner approach toward tourism. Although the U.S. has outlawed tourism to Cuba, the Treasury Department’s 12 categories for permitted travel include “educational activities,” and the Trump team says the Obama administration has stretched the definition too far.

“They feel that some of the individuals who are going to Cuba are doing so for purposes of tourism,” Mr. Kavulich said. “They’re looking at the marketing materials of the travel agents, the cruise lines taking tourists. They are not ideologues; they are taking strict legal viewpoints that there are 12 categories, and tourism isn’t one of them. That’s not what the Obama administration is doing.”

The White House is warning Trump officials not to reverse course and says Cubans are worried about the next administration’s intentions. The recent death of Cuban revolution leader Fidel Castro and the impending retirement of his 86-year-old brother, Raul Castro, also mean an unprecedented political transition on the island in the next few years.

“Turning it off would hurt the Cuban people,” Mr. Rhodes said. “It would cut off a lifeline to independent businesses. It would cut off a lifeline to Cuban families who depend on remittances. The new administration will have its own priorities to that engagement, but what we would not want to see is turning back the clock to an approach that had completely failed for over 50 years.”

Mr. Kavulich said Mr. Trump and his advisers also are anticipating the symbolism of elections in Cuba in February 2018 when Mr. Castro will be replaced, likely by Vice President Miguel Diaz-Canel, a civilian. That means Mr. Trump will be in office when Cuba is no longer ruled by the Castro family, regardless of the pace of democratic reforms.

“Trump is going to be in office as the first president in 59 years who will preside over a succession and a transition from a Castro to someone else,” Mr. Kavulich said. “If you’re in the White House you’re salivating at something like that. The bottom line will be, there’s not one [Castro] as president of the country anymore. And President Donald Trump will be the guy who’s in the White House when that happens. They absolutely get that.”

Intelligence fears

The Obama administration’s reopening of ties with Cuba is also raising concerns about Havana’s vaunted intelligence services and espionage against the U.S.

Ms. Quintana calls Cuba “a known seller of U.S. intelligence.”

In a little-publicized case in 2014, a spy for Cuba was sentenced to 13 years in prison in the U.S. The spy, who hasn’t been identified, worked out of the National Reconnaissance Office in Chantilly, Virginia.

Chris Simmons, a retired official from the Defense Intelligence Agency, said spying on the U.S. can be a lucrative business for Cubans, with clients such as China and Iran.

“Cuba doesn’t have a satellite program,” Mr. Simmons said. “So why would Cuba invest in sustaining someone who could only tell them everything about U.S. spy satellites? Because the countries we were targeting would undoubtedly pay a lot of money. There is an international audience for the barter and sale of U.S. secrets. Whether it’s Russia or China, there’s an insatiable appetite for what they can steal from us.”

Mr. Simmons also pointed to the case of Ana Montes, the “Queen of Cuba,” an American who stole U.S. military secrets for Havana from 1985 to 2001 while working as a top analyst for the DIA. Among her most damaging acts, she passed information on the location of U.S. Special Forces in El Salvador in the 1980s and provided the identities of four U.S. covert intelligence officers working in Cuba.

“For most of its history, Cuban spies have been volunteers, so there’s never a money trail. Ana Montes never got a salary,” Mr. Simmons said. “As long as we perpetuate the myth that Cuba’s not a threat, they’re going to clean our clocks and give that information to our enemies.”

He said he is concerned that three former high-level spies for Cuba are involved in their country’s engagement with the U.S.

They include Nestor Garcia Iturbe, who was Cuba’s master spy as director of the Superior Institute of Intelligence (ISI), where Cuban intelligence officers are trained.

“We’re negotiating with people we threw out for espionage,” Mr. Simmons said. “The bigger concern is, over the years, after the Cold War, the intelligence services and the military have become key players in the economy. The [Castro] brothers were very clever in terms of putting those two services in charge of key sectors, such as tourism. You’ve got the intelligence and military services becoming profit-making centers in their own right.”

He doubts that freedom will come to Cuba as Mr. Obama envisions.

“There is an elitist attitude around Washington that more exposure to Americans will introduce democracy and all these great values,” Mr. Simmons said, “as if the Canadians and Europeans weren’t able to do that. It hasn’t happened. There’s nothing we’re going to bring to Cuba that our allies weren’t able to introduce.”

Ms. Quintana said the Obama administration and its allies also have been misleading Americans with a narrative that Cuban-Americans’ attitudes are changing and that they no longer support the U.S. trade embargo of Cuba. She pointed to the election victories this year of candidates such as Sen. Marco Rubio, a Florida Republican and a Cuban-American who is an outspoken opponent of the Obama administration’s policy toward Cuba.

“A big indicator of how successful President Obama’s legacy has been is, look at the South Florida elections,” she said. “Every candidate who was a pro-embargo candidate won. It’s only through a positive political transition on the island that Cuba will become successful. You cannot have a successful economy without the rule of law. That’s not going to exist with the Castro regime in place.”

Sign up for Daily Newsletters Manage Newsletters

Copyright © 2020 The Washington Times, LLC. Click here for reprint permission.