The A-List Celebrities Who Used to Flock to Trump's Mar-a-Lago Estate in the 90s

Michael Jackson and Elvis's daughter honeymooned there, but they weren't Trump's only famous friends.
April 25, 2017, 2:49pm
Photo by Donna Connor, courtesy of Getty Images

Today, President Donald Trump spars with Meryl Streep and socializes with Sarah Palin and Pamela Anderson's ex-husband Kid Rock, but once upon a time, Trump vacationed with Hollywood's biggest stars. Anna Wintour and Sarah Jessica Parker attended his 2005 wedding to Melania, and his Mar-a-Lago country club, now "White House south," functioned as a meeting spot for pop culture behemoths like Sean "Puffy" Combs (now P Diddy), Celine Dion, and Michael Jackson—celebrities who built their careers from the bottom up.


Trump employed Dion to perform at Mar-a-Lago to show off to Palm Beach old timers that despised him, and J. Randy Taraborrelli reports in his definitive biography Michael Jackson: The Magic, the Madness, the Whole Story that Jackson and his first wife, Elvis' sole child Lisa Marie Presley, consummated their relationship at Trump's Palm Beach resort.

"It was romantic," Trump said according to Taraborrelli. The author claims the couple held hands and frolicked on the sandy beach. "Later, I asked Michael how things were going," Trump recalled. "He said, 'Great. I just got to kiss the most beautiful girl in the world. I hope I'm worthy of her. I think I might marry her."

The couple went on to spend their honeymoon at Mar-a-Lago in 1994 followed by a trip to the pink Disneyland Hotel located at Euro Disney Resort (now known as Disneyland Paris). When they returned to the United States, Mr. and Mrs. Jackson shared an NYC apartment in Trump Tower located beneath Trump's own all-gold home. Last year, Trump told ABC News Jackson was "a very good friend" and "he lived in Trump Tower for a very long time." (White House Press Secretary Sean Spicer and Presley's agent did not return Broadly's request for comment.)

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In the mid-1990s, both Trump and Jackson collaborated with then A-list hip-hop impresarios. Jackson and the Notorious B.I.G. recorded a duet, "This Time Around," for Jackson's 1995 album HIStory, and Trump was the Nicki Minaj of 1998, recording guest verses forPras's Ghetto Supastar and Method Man's Tical 2000: Judgement Day.

Today, this seems especially odd considering the unearthed reports about Trump's father, real estate tycoon Fred Trump, who owned rental apartments in Queens, refusing to serve black lessees. (The Trumps have denied the allegations.) On the hip-hop records, Trump sounds like a white dad attempting to impress his kids. "Hey Method Man, this is Donald Trump and I'm in Palm Beach and we're all waiting for your album," Trump said in Method man's "Donald Trump (Skit)." "Let's get going, man, everybody's waiting for this album!" On Pras's joint, Trump left a voicemail that serves as "1st Phone Interlude." It could have come straight out of last year's election: "Now after knowing you, I know that you're going to be right up there, and I hope very soon you're going to be in the leagues with me. So good luck."

Trump had earned so much hip-hop cred that Nancy Jo Sales profiled him for Vibe.

Like most of Trump's business ventures, his hip-hop endeavors collided with his personal life. Trump chilled with DJ Funkmaster Flex in the Hamptons and sat on a throne at a birthday party for P Diddy, then Jennifer Lopez's lover known as Sean "Puffy" Combs. Combs and Lopez even celebrated one Easter at Mar-a-Lago according to Vanity Fair. By May of 1999, Trump had earned so much hip-hop cred that Nancy Jo Sales profiled him for Vibe.

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"You are not talking to Puff Daddy!" Ivanka exclaimed when she saw her dad watching the Super Bowl with Combs, according to Sales.

Most Americans may agree with Ivanka's assesment, but Sales drew similarities between Trump and hip-hop stars. Although Trump told her he had "never heard of Method Man" until rap mogul Russell Simmons introduced them (Trump was still unsure who Pras was), Sales reported that Trump's bond with rappers stemmed from his chosen image as a bootstrapping entrepreneur from Queens who built towers in Manhattan to the chagrin of old money families.

Trump's reputation is half lie. He inherited money from his father, but Buzzfeed also reports that as a teenager in Queens, Trump stared at Manhattan obsessively. He wanted to cross the river and make his family famous in Manhattan and abroad. He attended University of Pennsylavia's Wharton School of Business, and returned to New York determined to show Manhattanites what was what. He went on to build large towers around Central Park and gravitate towards bombastic interior decorations. Like Michael Jackson, who grew up in a two-bedroom house in Gary, Indiana and went on to become one of the most famous musicians of all time, Trump loves gold statues. Explaining his admiration for the real estate tycoon, Method Man told Vibe, "I like his style."

"Trump grew up working construction sites. That is also why he talks like that—which is so great," Ann Coulter explained to me outside a Starbucks in a previous VICE article. "It is like a Shakespearian play: There is high comedy and low comedy. Trump is hitting it exactly right. That is, both his grammar is his simpatico with them, and he has always been like that."

Sales chose to sum the phenomenon in a, well, stranger way that would draw her into Twitter controversy today. "If Bill Clinton is, as Nobel Prize-winning author Toni Morrison insists, 'the first black president, then, using the same weird logic, Trump may be the first African-American billionaire," she writes.

The line has not aged well.