Analysis: The next U.S. president’s Cuba policy: Donald Trump

This article is the first of two on the leading U.S. presidential candidates and their expected Cuba policies

TrumpBy Timothy Ashby

This article is the first of two on the leading U.S. presidential candidates and their expected Cuba policies; Hillary Clinton’s anticipated policies will be the subject of an article following the Democratic Party convention.

Regardless of which candidate enters the White House next January, a continuation of the Obama administration’s policy of engagement with Cuba can be expected. Hillary Clinton has been an advocate for better relations with Cuba since her service as Secretary of State, and Donald Trump was the only Republican candidate (except Rand Paul) during the primaries who openly supported rapprochement, despite the criticism of rivals such as U.S. Senators Ted Cruz and Marco Rubio.

Trump has evolved in his approach to Cuba. In 1999, he published an editorial opposing business with Cuba on moral grounds.

“Yes, the embargo is costly. If I formed a joint venture with European partners, I would make millions of dollars. But I’d rather lose those millions than lose my self-respect,” he wrote, claiming he had turned down offers to partner with European investment groups to develop properties on the island. “I had a choice to make: huge profits or human rights. For me, it was a no-brainer.”

Several months later, Trump told the Cuban American National Foundation that Fidel Castro had “been a killer, he’s a criminal and I don’t think you should reward people who have done what he has done.”

Today, Trump advocates diplomacy with Cuba. This is a view contrary to the Republican Party platform, which states that “the current Administration’s ‘opening to Cuba’ was a shameful accommodation to the demands of its tyrants. It will only strengthen their military dictatorship.”

In September 2015, The Daily Caller, a conservative Washington publication, asked Trump: “Do you think Obama’s rapprochement is good policy, or do you oppose America’s opening with Cuba?”  The candidate responded: “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.”

When asked to respond in writing to the question “Do you support President Obama’s move to lift the trade and travel embargo on Cuba?”, Trump responded, “Ultimately, it’s going to be good,” adding that the U.S. government could have “made a better deal” and wished the United States was better at negotiating.

What can be expected from a Trump administration on specific Cuban policy issues?

Conditions for repealing the embargo

Trump is at odds with the Republican platform on ending the embargo, which calls “on the Congress to uphold current U.S. law setting conditions for the lifting of sanctions on the island: Legalization of political parties, an independent media, and free and fair internationally-supervised elections.” Trump is a pragmatist and believes that unrestricted commercial relations with Cuba are the best way to promote free enterprise and a better standard of living for the Cuban people. Although personally a non-smoker and teetotaler, Trump favors allowing U.S. imports of Cuban rum, cigars and other agricultural products, and thinks that U.S. hotel and real estate developers should not be restricted from investing in Cuba when foreign companies are profiting from the growing volume of American visitors to the island.  Trump Organization executives have visited Cuba to consider future golf course and hotel sites, and the candidate himself said he would be interested in opening a hotel there “at the right time, when we’re allowed to do it,” and that “Cuba would be a good opportunity ….”


Trump favors a settlement of both sides’ claims, but is concerned that any deal brokered with Cuba would lead the United States to get “sued for $400 billion or $1 trillion.” He is known to favor a “business approach” to claims settlement, stating “We don’t want to get sued after the deal is made …. I do agree something should take place. After 50 years, it’s enough time, folks. But we have to make a good deal and get rid of all the litigation that’s going to happen.”

Radio and TV Martí

Trump agrees with conservative Republican Sen. Jeff Flake that the $700 million of taxpayers’ dollars spent on Radio and TV Martí broadcasts is wasteful and should be stopped.


The Republican nominee wants to use the Guantánamo Naval Base as a bargaining chip in negotiations with Cuba, suggesting that the United States should “get them to take it over,” thereby saving $40 million a month. Although during the primaries he advocated “keeping it open and loading it up with bad dudes,” as president he would probably turn the U.S. naval station into a free zone for Cuban and foreign entrepreneurs, making best use of the new high-speed fiber optic internet cable connection to Florida, which cost $40 million.

The Cuban Adjustment Act

One of the few policies on which Trump and Marco Rubio jointly disagree with their Party is the Cuban Adjustment Act, the program dating from the Lyndon Johnson administration that enables Cuban immigrants to get welfare benefits from the moment they set foot on U.S. soil.  Both politicians want to see the legislation repealed.

Donald Trump may be many things, but he’s neither an ideologue nor a fool. On Cuba policy, Trump is more aligned with the majority of Republicans than with the Republican establishment that drafted the party platform. He and his policy team are aware that 56% of Republican voters recently surveyed by the Pew Research Center favored Obama’s Cuba policy, and 59% supported doing away with the embargo.

Dr. Timothy Ashby  served as a senior official responsible for Cuba trade policy in the Reagan and Bush administrations, and has been a policy advisor to several presidential candidates. He is a lawyer and founder and CEO of Pembury Capital, Ltd., a company that specializes in Cuban trade and investment strategies

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