The question of what Donald Trump intends to achieve in Cuba has become relevant since, as president of the United States, he assumed the power to “do whatever he wants” with the island.
“Whether it’s releasing it, taking it — I think I’ll be able to do whatever I want with it, to tell you the truth — they’re a very weakened country,” Trump said in March.
Earlier this month he insisted he could take hold of Cuba “almost immediately.” And this week he maintained that it is “a failed country and that it is only going in one direction: downwards!”
“Cuba is asking for help, and we are going to talk!!!,” Trump said in a message published on his Fact Social network this Tuesday.
As on previous occasions, the president avoided specifying exactly what he is looking for on the island.
Some predict that its purpose is to end the communist government that Cuba has had for more than 60 years, a long-standing objective of Washington.
Others suspect that he intends to change only the head of Cuban power and leave the current regime almost intact, but under his influence, to open business there for the US as he did in Venezuela since January.
If Trump has a defined plan in Cuba, it is an enigma even when he applies maximum pressure on the country, blocking its oil supplies and thus aggravating its colossal internal crisis.
But one thing is certain: Trump has contemplated possible economic opportunities in Cuba for years, despite the US embargo on the island.
He did it in a secretive way, as a real estate businessman, long before he became president and proclaimed himself all-powerful over that nation.
In fact, his company even registered the “TRUMP” trademark in Cuba for possible businesses in various areas, according to documents published by the White House.
“I think there is no doubt that Mr. Trump was very interested in the possibility of either putting the Trump brand on a Cuban resort, or perhaps even owning golf courses in Cuba,” says William LeoGrande, a professor at the American College in Washington, expert in US policy towards Latin America, in conversation with BBC Mundo.
Although none of these deals have come to fruition so far, Trump himself left open some time ago the possibility of doing so one day, “at the right time.”
A special trip
The first reported approach of a Trump company to Cuba records from 1998.
That year, the Trump Accommodations & Casino Resorts firm secretly sent consultants to Havana in search of business opportunities, as revealed by Newsweek magazine in 2016.
The publication, based on interviews with former Trump executives and business and judicial documents, stated that the company spent at least US$68,000 on the trip, which, according to one of the sources, included contacts between Trump representatives and officials of the Cuban government, then chaired by Fidel Castro.
And he added that, with Trump’s knowledge, that money was channeled through the American consulting firm Seven Arrows Investment & Style Corp., which suggested linking it to a Catholic charity to give it a legal appearance under the embargo.
This information emerged shortly before the first presidential elections won by Trump, who responded quickly: “I never did anything in Cuba. I never closed a deal in Cuba,” he said.
His spokesperson at the time, Kellyanne Conway, told the ABC television network that from the published article she understood that “they paid money” in 1998, and denied that Trump had invested in Cuba.
These revelations in the midst of the election campaign led Trump’s rivals to accuse him of violating the decades-old embargo on Cuba despite opposing the normalization of relations with the country undertaken by then-US President Barack Obama.
Robert Muse, a lawyer in Washington specialized in sanctions against Cuba, points out that legally “in 1998 it would have been necessary to obtain a specific license authorizing travel” to the island.
“And OFAC (a US Treasury office that applies international economic sanctions) would not have granted it if the purpose of the trip was to learn about commercial or investment possibilities in Cuba,” Muse tells BBC Mundo.
“Some potential”
Until the 1959 revolution, Cuba was an explicit destination for tourists and US investors in hotels, casinos and nightclubs.
But after coming to power, Castro’s government nationalized foreign businesses on the island, including American hotels.
A symbol of this transition from capitalism to socialism is the former Habana Hilton hotel, a large tower built by the American firm Hilton in the Cuban capital shortly before the revolution: the new government came to control it in 1960, made it its temporary headquarters and renamed it Habana Libre.
Despite this historical background and the hostility that continued for decades between Cuba and the United States, there are signs that Trump maintained interest in doing business on the island in more recent times.
The TRUMP brand was registered this century in Cuba for possible operations in real estate, hotels, gastronomy, nightclub services, entertainment and sports activities among other areas, according to a financial statement of the president in 2025 published by the White House.
That’s something Trump companies have done in dozens of countries around the world.
The Cuban Industrial Property Office shows on its website that the registration in Trump’s name was requested in October 2008 by Leticia Bermúdez, a Cuban lawyer, and that it was approved in 2010 with an expected expiration date in October 2018.
Currently, in the legal state of the trademark it is “invalidated”.
Executives and advisors of the Trump Organization also traveled to Cuba on different occasions between 2011 and early 2013, according to information published by Bloomberg in 2016.
One of those businessmen, Edward Russo, then Trump’s environmental advisor on businesses linked to golf courses, denied to that medium that the trips were made on behalf of the Trump Organization and mentioned bird watching and “habitats” among the purposes.
But Eric Trump, son of the current US president, seemed to indicate that the trips had another purpose.
“Although we are not sure if Cuba represents an opportunity for us, it is important that we understand the dynamics of the markets that our competitors explore,” he said in a statement at the time as executive vice president of the Trump Organization.
The dates of the trips coincide with the prelude to the thaw between Washington and Havana under the Obama government, which opened business possibilities in Cuba.
Lawyer Muse explains that “in 2011 and 2012 there was a general license to carry out professional investigations in Cuba, but these had to be academic, not commercial, in nature.”
It is unknown how long exactly Trump viewed Cuba as a place to eventually conduct personal business.
When asked by a CNN journalist in March 2016 if he would open a resort in Havana, Trump replied: “I would, at the right time, when we’re allowed to do it. Right now we can’t.”
“I think that Cuba has a certain potential and that it is good to integrate Cuba, but a much better agreement must be reached,” he said, referring to the normalization of relations negotiated by Obama.
However, shortly after the Republican was elected US president that year, the leader of a Spanish tourism multinational with investments in the Caribbean country said: “Trump until recently has been trying to negotiate hotels he wanted to have in Cuba.”
“Not more than six months ago,” added Miguel Fluxà, president of the Iberostar Group, as reported by the Spanish newspaper ABC on December 1, 2016.
“A beautiful island”
Before becoming president, Trump indicated that his businesses would pass into a trust managed by his children. However, many consider this insufficient to avoid conflicts of interest.
BBC Mundo asked the Trump Organization if it maintains interest in possible business projects in Cuba, but did not receive a response until the publication of this article.
Moments before mentioning the possibility of “taking” Cuba on March 16, Trump spoke of the country’s tourist advantages.
“Cuba in its own way, tourism and everything else, is a beautiful island: a magnificent climate,” he told reporters.
It is also not possible to know how much Trump’s business vision influences his policy towards that country.
Professor LeoGrande, an expert in relations between the US and Cuba, believes that this will be known based on the demands that Washington makes to Havana in the negotiations that both parties admitted to having in reserve.
“If the US were to settle for an agreement that involved mainly or only economic concessions,” LeoGrande reasons, “then it would be easy to say clearly that Trump’s background as a businessman (…) and his interest in Cuba as a business opportunity played an important role in determining the outcome.”
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