Trump's Secret Business Interests in Havana Unveiled by BBC

Long before Donald Trump claimed he'd wield power to "do whatever he wants" with Cuba, he covertly explored business prospects on the island. Plans for a hotel bearing his name, golf courses, and casinos were among his ambitions, according to documents and testimonies reviewed by BBC Mundo.

The first documented interest dates back to 1998, when Trump Hotels & Casino Resorts paid at least $68,000 to the consultancy Seven Arrows Investment & Development Corp. to send emissaries to Havana in search of opportunities in hospitality and casinos.

A 2016 Newsweek investigation revealed that this money was allegedly disguised as a donation to a Catholic charity called "Carinas Cuba" to give it a legal facade under the U.S. embargo.

Robert Muse, an attorney specializing in Cuban sanctions, was clear about the legality of this exploratory venture in Havana. "In 1998, it would have been necessary to obtain a specific license authorizing the trip. And OFAC wouldn't have granted it if the trip was for exploring commercial or investment opportunities in Cuba."

When these revelations surfaced during the 2016 presidential campaign, Trump firmly denied ever finalizing any deals with the Cuban government. "I never did anything in Cuba. I never made a deal in Cuba," he stated. His spokesperson, Kellyanne Conway, acknowledged to ABC that money was paid in 1998 but denied any investments by Trump on the island.

According to the BBC, a decade later, the Trump Organization took a further step by officially registering the "TRUMP" trademark in Cuba with the Cuban Office of Industrial Property, submitting the application on October 28, 2008. The registration covered three categories: financial services and real estate investment, entertainment and golf tournaments, and hotel and restaurant services.

To handle the process, Trump hired Cuban attorney Leticia Laura Bermúdez Benítez as a representative on the island. The trademark expired in October 2018, two years after Trump assumed the presidency.

The envisioned projects included a Trump Tower in Havana, a golf course in Varadero, and casinos, but these plans never materialized.

Trump's Public Statements and Expert Opinions

In public statements from 2015 and 2016, Trump did not conceal his interest in investing in the island's tourist areas. "Yes, at the right time, when we're allowed to do it," he told CNN in March 2015 when asked if he would open a hotel in Cuba. A year later, he summarized his stance in three words: "Cuba has potential."

William M. LeoGrande, a professor at American University in Washington and an expert on U.S. policy towards Latin America, commented on the matter to BBC Mundo. "I think there's no doubt that Mr. Trump was very interested in the possibility of either putting the Trump brand on a Cuban hotel or even perhaps owning golf courses in Cuba," LeoGrande said.

The paradox is striking: while Trump criticized Barack Obama's normalization deal with Havana during his campaign, his own executives had been exploring business opportunities on the island for years.

Now, as president in his second term, Trump has ramped up pressure on the Cuban regime with over 240 sanctions. This week, he declared, "Cuba is asking for help, and we're going to talk!" He described the island as "a failed country heading only one way: down!" Analysts debate whether his true aim is to dismantle the communist dictatorship or merely change the power structure to open new business opportunities for American entrepreneurs, as he did in Venezuela since January 2026.