Trump's Long History With Venezuela's Elite Before He Decided To Fix It

President Donald Trump's years-long crusade to dislodge Venezuelan strongman Nicolas Maduro, a mission he finally accomplished this month, was billed as a way to thwart drug trafficking, check migration and revive Venezuela's oil industry. But behind the president's preoccupation with the South American nation is also the story of lifelong personal and business relationships with Venezuelan elites in New York and Miami.

From this tiny privileged class whom he got to know as a military academy student and jet-setting businessman, Trump would have absorbed memories of a country where petrodollars built a clutch of glittering fortunes not unlike his own, according to people familiar with his social interactions. That was before the 1990s rise of socialist icon Hugo Chavez, who seized on Venezuela's vast inequality and corruption to drive one of Latin America's wealthiest economies onto a path of ruin. Maduro - and then US sanctions - made it worse.

Although there isn't any evidence that he ever visited Venezuela, Trump's own words suggest that this riches-to-rags chronicle of more than a quarter century helped fuel his determination to restore the country to its former glory.

Venezuela is "a country I know very well, for a lot of reasons," Trump said during his second inauguration day in 2025. "It was a great country 20 years ago, and now, it's a mess," he said - comments that he echoed last week at the World Economic Forum in Davos.

Trump's storied business career includes competing with, and ultimately outbidding, Venezuelan billionaire Gustavo Cisneros, whom he admired, to buy the glamorous Miss Universe beauty pageant in the mid-1990s. The purchase fired up Trump's media brand and helped lead to the NBC reality show "The Apprentice" that burnished his popularity.

After US forces captured Maduro in early January, Trump has been working with acting President Delcy Rodriguez, the regime's former No. 2, whom he said is "willing to do what we think is necessary to make Venezuela great again."

Asked to comment on the anecdotes in this story and Trump's relationships over the years with Venezuelan elites, Anna Kelly, a White House spokeswoman, said Trump has been clear that his motivation for arresting Maduro was because he was "sending drugs and criminals into our country at unacceptable rates."

"The President will do everything in his power to secure our homeland from those killing Americans with illicit narcotics," Kelly said.

Amigos on the Pitch

Trump's friendships with Venezuelan elites date as far back as his teenage years at the New York Military Academy, a prep school nestled in the Hudson Valley. He played on the varsity soccer team in the early 1960s, when soccer was still niche in the US. Trump was one of the few non-Hispanic players on a team dominated by surnames like Rosas, Rocha and Jaramillo, according to a yearbook from the school.

"The soccer team was like a fraternity," Isilio Arriaga, a Venezuelan-American friend and classmate of Trump, said in an interview. "He knew about Venezuela since he was a young kid, and he had a special caring for our people, for Latinos in general."

When Trump moved to Manhattan in the early 1970s, he joined Le Club, then one of the city's most exclusive social clubs and one frequented by wealthy South Americans, the president wrote in "Trump: The Art of the Deal."

When Trump was a rising real estate developer in the early 1980s, Diego Arria, a former governor of Caracas and UN ambassador, introduced Trump, then in his mid-30s, to Italian-Argentine businessman Franco Macri, two decades his elder and father of Argentina's future president Mauricio Macri. The connection ultimately led to Trump buying a controlling interest in the Lincoln West project in Manhattan from Macri in 1985. Arria, in an interview, said that he and his wife became some of the first friends to visit Trump at Mar-a-Lago after he bought it as a private residence that same year.

In the mid-1990s, Trump met Cisneros, dashing patriarch of the Venezuelan family that was once the richest in South America and owner of the Miss Venezuela pageant, among the world's most prestigious beauty contests. Trump, who in the 1980s had opened casinos in Atlantic City, home of the Miss America pageant, became interested in buying the rival Miss Universe when it came up for sale in 1996. Trump went to meet Cisneros, co-founder of Spanish-language media empire Univision, for breakfast at the Venezuelan magnate's Fifth Avenue apartment, "an absolutely magnificent blocklong duplex," Trump later recounted in his book "Trump: The Art of the Comeback."

Trump remembered Cisneros as "dazzlingly handsome" and said that "if I were casting a movie whose male lead was to be South American aristocracy, the role would go to him," adding "I learned something about style that morning." After briefly raising the idea of a partnership, Trump outbid him for the pageant.

"There were several meetings with Mr. Trump to discuss the acquisition of the Miss Universe pageant," recalls Beatrice Rangel, who served as deputy chief of staff to Carlos Andres Perez, the socialist-turned-neoliberal Venezuelan president whom Chavez tried to oust in a 1992 coup attempt. She later became a senior adviser for the Cisneros Group before the Miss Universe sale. "These conversations did not render any fruit in terms of a partnership, because Mr. Trump wanted to have the asset for himself."

During the two decades when Trump owned Miss Universe until 2015, four Venezuelans won the crown - establishing the country's brand as a pageant powerhouse in that era.

"It may be that Trump remembers Venezuela during its boom years, when the Miss Venezuela pageant was a huge spectacle, and Trump is undoubtedly a man who loves spectacle. It holds a special fascination for him," said Giovanna De Michele, a Venezuelan international affairs analyst.

The family of Gustavo Cisneros's cousin, soft-drink and telecoms mogul Oswaldo Cisneros, also knew Trump and his first wife Ivana socially, once renting an apartment in Trump Tower, right below the future president's apartment. 

"I'd have a cocktail party, and they'd go downstairs. They'd have a cocktail party, and I'd go upstairs," recalled Oswaldo's widow, Ella Fontanals-Cisneros, at an event in 2024 to promote a book.

The pageant circuit gave Trump opportunities to mingle with Venezuelan models at parties. He also established a professional relationship with flamboyant Cuban-Venezuelan Osmel Sousa, known as the "Beauty Czar," who prepared the women for competition.

"During the years that Donald Trump owned Miss Universe, whenever he saw me he would call me 'my king of Venezuela'," Sousa recounted in his biography titled "Osmel: An Unknown Man."

Arria, the former Caracas governor, remained friendly with Trump in the 1990s, and said that at one point Trump asked him to reach out to Sousa and attempt to hire him for Miss Universe. Arria says that Sousa declined the overture.

Paradise Lost

Decades later, President Trump has ironically embraced Rodriguez, who rose to power under Chavez's ideological banner of redistributing wealth. At the same time, he's sidelined opposition leader Maria Corina Machado, a US boarding school graduate like himself whose father headed Sivensa, a company that saw its steelmaking subsidiary expropriated by Chavez in 2010. Still, after a recent meeting with Machado, Trump said he was "impressed" with her and thought she might be "involved in some way" in Venezuela's reconstruction.

That nascent process is imbued with Trump's musings about Venezuela's squandered glory, which have surfaced even during moments of high political stakes.

On Feb. 5, 2020, Trump hosted then-opposition leader Juan Guaido at the White House for the first time. Trump a year earlier had recognized Guaido, then head of Venezuela's National Assembly, as the country's rightful president and imposed "maximum pressure" sanctions in a bid to oust Maduro after the US and other countries alleged fraud in a 2018 election.

During a conversation about how to bring about change in Venezuela, Trump turned to the teams assembled and asked for the name of the man who prepared the Venezuelan contestants for Miss Universe, according to people with knowledge of the meeting.

Flabbergasted, the Venezuelans fumbled to respond. Finally someone suggested: "Osmel Sousa."

Trump excitedly confirmed that was the person he had been thinking of, the people said, and his fondness for the man and the lost era came pouring out.

Arriaga, Trump's classmate, returned to Venezuela after college and went on to have a career in business and politics for three decades before moving back to the US. He saw Trump at Mar-a-Lago a few years ago, between his presidential terms, as a guest of another friend. Arriaga recalls that Trump immediately greeted him by exclaiming "Chico!" -  Arriaga's childhood nickname.

They reminisced about their academy days. Before leaving, Arriaga made a plea: "Mr. President - don't forget about Venezuela."

"I will never forget this," Arriaga said in the interview. "He said to me, 'I'm on it.'"
 

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