Despite earlier promises in Miami that he would not do business in Cuba until the island was “free,” Donald Trump applied in 2008 to register his Trump trademark in the Caribbean nation for a variety of commercial activities, including investing in real estate, hotels, casinos and golf courses.

A search of the Cuban Industrial Property Office database shows that Donald J. Trump hired a Cuban lawyer, Leticia Laura Bermúdez Benítez, to submit the application in October 2008. The address listed was that of the Trump Organization: 725 Fifth Avenue, New York, 10022.

As is common in Cuba, where red tape is rampant, the trademark was not approved until much later, until March 2010. It expired in 2018, well into Trump’s presidency.

According to a description of his application, appearing both in the official Cuban registry website and in a 2009 bulletin, the trademark was related to “investment in real estate,” “beauty contests,” “golf courses,” “casino game services,” “montage of television programs,” and “hotel services,” among many other activities listed.

While President Trump might have broken his word about not seeking business in Cuba, given during a 1999 speech at the Cuban American National Foundation in Miami, he did not violate the U.S. embargo against Cuba in filing the application or hiring the Cuban lawyer. The Cuban Assets Control Regulations, the Treasury Department’s rules to implement the trade embargo, include exceptions to allow the filing for trademarks and the payment of local agents to do so.

The Herald could not immediately contact Bermúdez Benítez. The White House referred questions to the Trump Organization. The latter also did not respond to a request for comment.

Hundreds of American companies, including Netflix, Disney, Apple, Microsoft, and Starbucks, rushed to register their trademarks in Cuba after the two countries re-established diplomatic relations in 2015. At the time, several law firms encouraged their clients to do so because “Cuba is a ‘first to file jurisdiction,’ which means a Cuban trademark registration will be awarded to the first applicant, even if that applicant has not previously used the mark,” according to a client notice issued by the law firm Hunton & Williams.

President Trump has imposed several new sanctions on the Cuban government and strengthened the embargo, citing human rights violations and the regime’s support to Nicolás Maduro in Venezuela. His strong rhetoric against the government in Havana has given him the crucial support of many Cuban American voters in Florida.

But his flirtations with business on the island spanned decades.

In 1998, a Trump company, Trump Hotels & Casino Resorts, paid a consulting firm around $68,000 for a business trip to Cuba on its behalf, in a likely violation of the embargo at the time, according to a Newsweek report.

More recently, in 2013, executives from the Trump Organization visited Cuba to explore investing in a golf course east of Havana, in an area known as Bello Monte, Bloomberg Businessweek reported. And the CEO of a Spanish hotel chain declared that the Trump Organization was looking into establishing hotels on the island when Trump was a presidential candidate in 2016.

His former presidential campaign manager, Paul Manafort, also traveled to Cuba in January 2017, according to a Senate report.

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