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Two Years After U.S.-Cuba Opening, What’s Next Under Trump?

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Passengers on board Carnival's Adonia cruise ship wave flags as they arrive from Miami in Havana, Cuba, Monday, May 2, 2016. Joe Cavaretta / AP

MIAMI, Fla. — After recently returning from her first trip to Cuba, Elizabeth Díaz, 24, went to her grandmother’s house to show her pictures of the home she left behind in 1962. It still had the same furniture. Her grandmother cried looking at pictures of where she had gotten married decades earlier and the grave where her parents are buried.

Díaz is among the Americans who have recently visited Cuba for the first time now that flying there is easier. “I have always wanted to go, since I can remember.”

Two years ago on Dec. 17, 2014, Barack Obama and Raul Castro surprised the world when they announced on a Wednesday morning they would reestablish diplomatic relations after more than half a century of hostility.

Watch Raul Castro Greet President Obama in Cuba 0:39

Since then, the two countries have opened embassies and restored commercial flights. American cruise ships have begun docking in Cuba. Agreements have been negotiated on a range of issues including the environment, law enforcement, the postal service, and communications. Google recently signed a deal with Cuba to place computer servers on the island to speed their services.

But what happens next with U.S.-Cuba relations has been impacted by two political transitions: the death of Fidel Castro and a new administration in Washington starting in January.

There is looming uncertainty on the minds of Cuba watchers as to how president-elect Donald Trump will handle policy towards Cuba. As much as some analysts may think Fidel Castro’s death may open a door to changes in the island, it’s Trump’s presidency that will have a more far-reaching impact.

Eric Schmidt, chairman of Alphabet Inc. (L) and Mayra Arevich Marin, president of state telecommunications monopoly ETECSA, shake hands after signing documents in Havana, Cuba
Eric Schmidt, chairman of Alphabet Inc. (C-L), which owns Google, and Mayra Arevich Marin (C-R), president of state telecommunications monopoly ETECSA, shake hands after signing documents in Havana, Cuba, December 12, 2016. ALEXANDRE MENEGHINI / Reuters

Proponents of Obama’s Cuba policy say engagement has improved the lives of its residents and with time, it will bring democracy to the island. The embargo failed to remove the Castro regime after more than half a century and they feel everyday Cubans are the ones who have suffered most. Many are hoping Trump will approach Cuba from a business perspective.

RELATED: Cuba After Castro: How Much Change, and How Quickly?

Obama’s administration is now pressing Cuban officials to complete pending deals with U.S. firms before his term is up in January. Although U.S. companies have more freedom now to operate in Cuba, the communist government has been slow to give approval. Obama hopes closing enough deals will help make the diplomatic and commercial ties between the two countries irreversible.

Will Castro's death spark a new era in Cuba? 7:15

Obama, who in March became the first U.S. president to visit the island in 88 years, has gradually poked holes in the U.S. embargo through executive orders.

During his presidential campaign, Trump sent mixed messages about how he would approach these changes in policy. During the primary, Trump said he thought restoring diplomatic relations was “fine,” adding that the U.S. and Cuban people did not get enough in return. Then he said during a CNN interview in March he would “probably” continue having relations with Cuba but he would want “much better deals than we’re making.” But during a rally in Miami shortly before Election Day, Trump took a tougher stance, saying he would remove all concessions made by executive order “unless the Castro regime meets our demands.”

RELATED: After Obama's Visit, Cubans Debate Island's Future and Economy

Cuban officials have mostly refrained from commenting on Trump’s statements, waiting to see whether his tough talk materializes into policy change.

There are now more than half a million small business owners or cuentapropistas, many of which depend on tourism. Cuba had a record 3.5 million tourists visit the island last year, many of them Americans. If Trump were to end travel to Cuba the emerging class of entrepreneurs would take a serious hit.

In addition, U.S. businesses could lose hundreds of millions of dollars.

RELATED: 'An End of An Era,' Say Cuban Americans in Miami After Fidel Castro's Death

Pedro Freyre, an attorney who heads the international practice at Akerman LLP represents major U.S. companies who are seeking to do business in Cuba. He said American agricultural sales to the island alone have reached up to $700 million a year. Freyre questions whether the president elect would be willing to cut around 1,000 American jobs “that would go to the very heart of the states that supported Trump.”

What Could Freezing U.S.-Cuba Relations Mean for U.S. Agriculture? 1:03

The embargo in the balance

A large majority of Americans — 75 percent — approve of the decision to reestablish relations with Cuba, according to a recent Pew Research Center poll, and about the same number (73 percent) favor ending the embargo against the island. Among Miami's Cuban American community, under four-in-ten support the current embargo, according to a poll conducted by Florida International University in September.

Gustavo Arnavat, a former senior Obama Administration official and former Executive Director of the U.S. at the Inter-American Development Bank, thinks Trump has a chance at having the embargo lifted, something Congress has been reluctant to do. “The Democrats would certainly vote to end it, and my sense is he will have an easier time – in general – convincing enough Republicans to vote to lift it as well.”

Expert Weighs in on What's Next in U.S.-Cuba Policy Shift 9:42

Patrick Hidalgo, co-founder of Future Partners and an informal adviser to the White House on Cuba, said he wouldn’t be surprised if Trump negotiates a deal in a similar way he pressured the air-conditioning manufacturer Carrier Corp. to keep hundreds of jobs in Indiana instead of leaving for Mexico. “Get one or two concessions from the Cuban government and then make a big deal of it,” Hidalgo said.

One indication of the route Trump could potentially take is a look at the team surrounding him. Two of the most noticeable regarding Cuba policy are Mauricio Claver-Corone and Yleem Poblete. Claver-Corone, who is executive director of the pro-embargo U.S.-Cuba Democracy PAC, is now on the Treasury Department team. He has been a harsh critic of Obama’s policy.

Poblete, a former senior staff director of the House Foreign Affairs Committee for twenty years, is a member of the National Security Council team. Her husband, Jason Poblete, a Washington D.C. attorney who specializes in export controls and economic sanctions, said the U.S. embargo on Cuba has not worked because the government has not “enforced the laws the way Congress intended.” He said he is “extremely confident” that if the laws were enforced, the outcome would be very different.

Cuban-American members of Congress, such as Rep. Ileana Ros-Lehtinen, oppose ending the embargo. In a recent interview, she said she is holding Trump to his promise of removing "concessions" to Cuba made under Obama.

Rep. Ileana Ros-Lehtinen Answers: Should Trump Dissolve Obama's Cuba Policy? 6:11

For many Cuban exiles, human rights on the island are a key issue, and one which has not gotten better. The amount of short term arbitrary arrests “have increased dramatically in recent years,” according to Human Rights Watch.

The day Fidel Castro died, graffiti artist Danilo Maldonado, knows as “El Sexto” was dragged out of his house, beaten by authorities, and jailed for spray panting on a Havana hotel wall “se fue” or he’s gone and Human Rights Watch has called for his release. He is still in prison and on a hunger strike.

No one has been assigned specifically to Cuba, which usually involves the Bureau for Western Hemisphere Affairs at the State Department. But Rex Tillerson, who has been chosen as Secretary of State, was quoted in 2014, during an Exxon shareholder meeting saying “we do not support sanctions, generally, because we don’t find them to be effective unless they are very well implemented comprehensively and that’s a very hard thing to do.”

In Cuba, changes ahead too

Many Cubans, disillusioned with the slow economy of their country and taking advantage of the preferential treatment given to Cuban migrants under the Cuban Adjustment Act, have been streaming into the U.S. The amount of migrants nearly doubled in the past two years.

Many analysts think real change will begin when Castro’s likely successor, Miguel Diaz Canel, 56, steps in. He is currently the First Vice President of the Council of States. President Raúl Castro has said he would leave office in February 2018 after more than 12 years in the office. He has not said whether he will give up his role as commander of the armed forces, which runs the tourism industry.

Image: President Barack Obama listens as Cuban President Raul Castro speaks
President Barack Obama listens as Cuban President Raul Castro speaks during their news conference at the Palace of the Revolution, Monday, March 21, in Havana, Cuba. Pablo Martinez Monsivais / AP

In 2008, Fidel Castro officially handed over power to his brother knowing that dying in office could potentially spur chaos on the island. Though the elder Castro still had some political influence, his brother began introducing market-style reforms in 2011. The iron grip with which they have ruled the country remains strong.

Some caution that someone like Díaz-Canel, who is from a younger generation, may receive resistance from the hard line communists within the government, who have been suspicious of the opening with the U.S. and may want to put an end to economic reforms.

“Raúl Castro — precisely because of his role in the revolution and as head of the armed forces — would have an easier time selling normalization within Cuba domestically to the nay-sayers there,” said Arnavat. “The challenge is convincing the nay-sayers among the leadership in each country who still don’t trust the leadership of the other country."

At least for now, all eyes will be on Raúl Castro and Donald Trump.

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