Long before asserting power to "do as he pleases" with Cuba, Donald Trump secretly explored business opportunities on the island: a hotel bearing his name, golf courses, and casinos were among his plans, according to documents and statements analyzed by BBC Mundo.
The first documented approach dates back to 1998, when his company Trump Hotels & Casino Resorts paid at least 68,000 dollars to the consulting firm Seven Arrows Investment & Development Corp. to send emissaries to Havana in search of opportunities in hospitality and casinos.
According to a study by Newsweek published in 2016, that money was attempted to be disguised as a donation to a Catholic charity called "Carinas Cuba" to give it a legal appearance under the U.S. embargo.
The lawyer Robert Muse, who specializes in sanctions against Cuba, is adamant regarding the legality of that exploratory venture in Havana.
"In 1998, it would have been necessary to obtain a specific license authorizing the trip. And the OFAC would not have granted it if the purpose of the trip was to explore business or investment opportunities in Cuba."
When Newsweek published those revelations during the heat of the 2016 presidential campaign, Trump reacted sharply, warning that he never finalized anything with the Cuban government.
"Nunca hice nada en Cuba. Nunca cerré un trato en Cuba." His spokesperson Kellyanne Conway acknowledged to the ABC network that "they paid money" in 1998, but she denied that Trump had invested in the island.
BBC indicates that ten years later, the Trump Organization took it a step further and officially registered the trademark "TRUMP" in Cuba with the Cuban Office of Industrial Property, with an application submitted on October 28, 2008.
The registry covered three categories: financial services and real estate investment, entertainment and golf tournaments, and hotel and restaurant services.
To manage the process, Trump hired the Cuban lawyer Leticia Laura Bermúdez Benítez as his representative on the island. The trademark expired in October 2018, by which time Trump had already been in the White House for two years.
The proposed plans included a Trump Tower in Havana, a golf course in Varadero, and casinos, projects that never came to fruition.
In public statements made in 2015 and 2016, Trump did not hide his interest in someday investing in tourist areas of the island.
"Yes, at the right moment, when we are allowed to do so," he responded to CNN in March 2015 when asked if he would open a hotel in Cuba. A year later, when posed the same question, he summarized his stance in three words: "Cuba has certain potential".
William M. LeoGrande, a professor at American University in Washington and an expert on U.S. policy toward Latin America, addressed this topic in statements to BBC Mundo.
"I believe there is no doubt that Mr. Trump was very interested in the possibility of either putting the Trump brand on a hotel in Cuba, or perhaps even owning golf courses in Cuba," said the expert.
The paradox is striking: while Trump criticized during his campaign the normalization agreement promoted by Barack Obama with Havana, his own executives had been exploring business opportunities on the island for years.
Now, as president in his second term, Trump has intensified pressure on the Cuban regime with over 240 sanctions. This week he stated, "Cuba is asking for help, and we are going to talk!"
He described the island as "a failed country that is only heading in one direction: downward!" Analysts are debating whether his true goal is to end the communist dictatorship or merely to change the power structure to open new business opportunities for American entrepreneurs, as he did in Venezuela since January 2026.
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