• Mike Smallcombe

Donald Trump and Michael Jackson: The full story behind a mysterious friendship

Donald Trump's inauguration is upon us – the 45th President of the United States will take office just ten weeks after what was seen as the biggest shock in the country's electoral history.

Before trying his hand at politics, Trump was known as a billionaire real estate mogul and reality television star.

Trump was also no stranger to parading around with A-list celebrities and he long courted personalities from sports and entertainment, including pop superstar Michael Jackson.

It may come as a shock to Jackson’s daughter Paris that her father spent a significant amount of time in Trump’s company in the 1990s, with Trump going so far as to call Jackson “a very good friend of mine”.

As many Americans struggled to come to grips with a Donald Trump presidency in the wake of his election, Paris took to social media to share a picture of a man staring at a noose, revealing that she had a “feeling of impending doom” surging through her entire body. She also made the point that those who voted for Trump were defying her entire family.


Read next: Author Mike Smallcombe discusses his book Making Michael


It is important to remember that Jackson’s association and ‘friendship’ with Trump existed many years before the property tycoon turned to politics, and Jackson never had the opportunity to pass judgment on Trump’s professed beliefs and agendas.

Trump and Jackson on a private jet

The story of Donald Trump and Michael Jackson begins in March 1988, when the pair met backstage at a concert at New York City’s Madison Square Garden. Trump recalls: “I spoke to him for a little while, he was low-key, and I’d think, ‘There’s no way this guy is going out to that stage to perform’. And then you see him moonwalk across the stage and the place would go crazy.”

The two became properly acquainted in 1990, when Trump opened what was then the world’s glitziest casino, the Taj Majal in Atlantic City, New Jersey. Dubbed the ‘Eighth Wonder of the World’, the 1,250-room casino hotel was constructed at a total cost of $1.1 billion, making it the most expensive casino ever built.

Trump and Jackson goof around at the Taj Mahal in Atlantic City

On Friday, April 6, 1990 Jackson travelled to Atlantic City to assist Trump with the grand opening, and stayed in the hotel’s $10,000-a-night ‘Alexander the Great Suite’. “If I ever needed him for something, he’d always be there,” Trump later said. “He was very loyal to his friends.”

Jackson’s arrival at the Taj that afternoon caused pandemonium; thousands of screaming fans and dozens of photographers chased the pair as Trump gave his star guest a guided tour of the facilities.

“There were thousands of people literally crushing us,” Trump said, recalling the bedlam. “We had 20 bodyguards, but it was really dangerous.

Trump gives Jackson a guided tour around his Taj Mahal casino hotel in Atlantic City

“He dropped to his knees and started crawling to the exit. He did it so routinely, I thought he fell. And I said, ‘Michael, is it always like this?’ He goes, ‘Yeah, this is nothing. Japan is much worse’."

The next day Trump gave Jackson a tour of the Historic Atlantic City Convention Hall arena, adjacent to his Trump Plaza casino hotel. On the Sunday, Jackson was due to leave for Indiana to be at the bedside of his close friend, 18-year-old Ryan White, who was losing his brave five-year battle with AIDS.


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As he arrived at the airport, Jackson was told that Ryan had passed away. Trump, who was about to board his private jet to return to New York, told Jackson he would accompany him on the journey to the White family home, seemingly sensing a golden public relations opportunity.

Trump and Jackson on the tarmac at Atlantic City before flying to Indianapolis

The pair flew to Indianapolis together aboard a private jet provided by Jackson’s record label, before travelling the 20 miles to Ryan’s hometown of Cicero in a motorcade of three limousines and several police vehicles.

After arriving at the home, a grieving Jackson sat briefly in the back of a red Ford Mustang GT, which he had given to Ryan as a gift a year earlier. He told the waiting media: "He was a personal friend. It's sad.”

After extending his condolences to the family, Trump returned to New Jersey. Jackson remained at the house until the evening, reminiscing and looking through scrapbooks with Ryan's mother, Jeanne.

Jackson spent the next 18 months working on his Dangerous album, which celebrates its 25th anniversary this month. He and Trump crossed paths again in June 1992, at a charity gala held at the iconic Tavern on the Green restaurant in New York. Trump and his future wife, Marla Maples, accompanied Jackson as he collected an award for his efforts in helping economically disadvantaged children.


Read next: The making of Michael Jackson's Dangerous


Jackson, Trump and his future wife Marla Maples at Tavern on the Green in New York in June 1992

The Trump-Jackson friendship was at its strongest in 1994. In March that year, with a gruelling world tour and damaging child molestation accusations behind him, Jackson relocated to New York City to work on his next album, which became HIStory.

Jackson reportedly paid $110,000 a month to rent a four-bedroom apartment near the top of Trump Tower, high above Fifth Avenue in midtown Manhattan. The apartment, which offers spectacular views over Central Park, was put on the market earlier this year for a cool $23 million.

Trump Tower in New York City

Jackson’s friend, Frank Cascio, recalls the stay: “Michael’s apartment at Trump was over the top, with dramatic views and gold fixtures in the bathrooms. On the second floor there were three bedrooms. He transformed one of them into a mini dance studio by having all the furniture removed and putting in a dance floor.”

Jackson was living just a few floors below Trump's own $100m penthouse, where the pair would often spend time together. “He’d come into my apartment and we’d talk a lot about business,” Trump said. “He was actually a very, very smart businessman.”

Jackson's apartment boasted dramatic views of the Empire State Building and Central Park

One night, they went for dinner at Manhattan’s Le Cirque restaurant. “It was as if he had never seen a menu before, and we carefully went over each item,” Trump recalls.

“But what was most amazing were the looks on the distinguished faces in the room as they came over to our table practically begging for an autograph. These are people who had probably never asked for anyone’s autograph before, and I can guarantee you, it was not easy for them to do. They would always start by saying, ‘I have a son who is a big fan of yours, Mr Jackson. Could you give him an autograph’?

“But I believe it was for them, not their sons. One woman, one of the most socially prominent in New York, known for her attitude approached our table trying to look cool, then slightly tripped. She grabbed the table for support and asked in the same breath, ‘Mr Jackson, can I have your autograph’? It was amazing to see this woman, whom I have known for years, so flustered and nervous.”

Jackson hold Trump's daughter Tiffany in 1994

Trump says he was surprised when Jackson told him he had a new girlfriend. “I congratulated him and asked, ‘Who is it’? He was very shy and looked down into his napkin, then put the napkin over his face and said, ‘Trump, Trump, I don’t want to talk about it, I’m so embarrassed’. I chided him. When he finally looked up, he said that it was a girl named Lisa Marie [Presley, Elvis’s only child].”

A couple of weeks later, Jackson asked his host if he could bring his new love interest to Trump’s sprawling Mar-a-Lago estate in Palm Beach, Florida. “We flew down in my plane together,” Trump said. “On the flight down, he asked if it would be possible for his girlfriend to come over and stay. I said absolutely, I looked forward to meeting her. He said she would be arriving sometime around eight o’clock, about an hour after we got to the house.”

Trump's sprawling Mar-a-Lago estate in Palm Beach, Florida

Trump said that when Lisa Marie arrived, Jackson ran to the living room and greeted her with a hug, before they took off to look at the ocean. “When they came back, holding hands and hugging, they seemed very much in love,” Trump said.

During their week-long stay, Jackson and Lisa Marie spent nearly every evening in a part of the mansion called the Grand Tower, and left the house together just once.

“He was up there one week with her, and he never came down, so I don’t know what was going on, but they got along,” Trump said.

“People often ask me whether or not the relationship was a sham and I give them an emphatic no. I can tell you, for at least a period of time, these two folks were really getting it on.”

Jackson married Lisa Marie in a secret ceremony in the Dominican Republic in late May 1994, but they divorced 20 months later. Meanwhile, in December 1994 Jackson finally checked out of Trump Tower after a nine-month stay and returned to California to complete the HIStory album.

Jackson with Trump's children Ivana and Eric at Mar-a-Lago in 1994

At this stage, it would have seemed like the two were good friends. But then Jackson decided to subtly include Trump in the lyrics of one of the HIStory album's tracks, 'Money', which is an attack on greed and ruthless and unethical individuals.

At one point the background vocals feature the words, 'If you want money, then earn it with dignity', before Jackson speaks the names of several American industrialists and business magnates, including Trump, Cornelius Vanderbilt, J. P. Morgan, John D. Rockefeller, Andrew Carnegie and J. Paul Getty.

Somewhat surprisingly, the lyrics were subtle enough to avoid any major headlines in the media. It would appear that although the pair shared a business relationship, Michael's true feelings about Trump came to light through those lyrics.


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But Brad Buxer, who worked on the song as a producer and musician, says there was never a falling out between the pair and that the lyrics were not meant as a personal attack on Trump.

"I was around Michael Jackson constantly, and we talked about everything," Buxer said. "There was no falling out between him and Donald Trump; Michael thought the world of him. Michael loved and greatly admired successful people, and was truly inspired by Trump. He thought he was an amazing businessman, respected him greatly and liked him very much.

"He would have called out Donald Trump's name out of respect and admiration. Sometimes in Michael's music his lyrics and their meaning would be misunderstood. 'They Don't Care About Us' is an example where some people thought his lyrics were racist."

A note Jackson wrote to his assistant in 1990: 'Where's footage of Trump's speech about me'?

One of the individuals Michael admired included Thomas Edison, an American inventor and businessman with links to Morgan, Vanderbilt and the controversial motor company founder Henry Ford, who Michael also once praised.

When discussing the notion of not giving up in the face of adversity in a recorded conversation with a friend in 2004, Michael said of Edison and Ford: "Some of the greatest men who have made their mark on this world were treated like that - you know, 'You're not gonna do it, you're not gonna get anywhere'.

"They laughed at the Wright brothers. They laughed at Thomas Edison. They made jokes about Henry Ford. They said he was ignorant. These men shaped and changed our culture, our customs, the way we live, the way we do things."

Either way, Jackson and Trump met again half a decade later, which would indicate that there was no fallout. Jackson called Trump when he was staying in New York to record his Invincible album, and invited the businessman and his partner Melania for dinner at the luxury Pierre Hotel.

Melania, who married Trump in 2005 and will become the next First Lady of United States, recalls how she hit it off with Jackson. Melania said: “Just after dinner, we were chatting on the sofa and my husband went into another room to see some art somebody wanted to show him. And Michael said to me, 'Hey, when Trump comes back, let's start kissing so he will be jealous’!” The two didn’t kiss. "But we were laughing so hard,” she says.

Trump with (L-R) Jackson's mother Katherine and sisters Janet, Rebbie and La Toya

In 2004, Trump publically defended Jackson ahead of his child molestation trial. “I'm going to stick up for him, because nobody else is,” Trump told Larry King. “But I don't believe it.

“He lived in Trump Tower. I knew what was happening with Michael Jackson. You know what was happening? Absolutely nothing. I had many people that worked for me in the building, and believe me, they would tell me if anything was wrong.

“And if you look at the mother of this young man [Gavin Arvizo], she has had plenty of experience at going after people. And she goes after them viciously and violently, and I saw a story and I read another story about some of the things she's done.

“It's tough to win [a trial]. But I have a feeling he is going to win.”

Trump later reiterated his point, and said his young children were often in Jackson’s company when he was living in Trump Tower in 1994. “Michael would spend a lot of time with my kids,” Trump said. “Michael would come, play with the kids. He just loved children. He was not a child molester and I am certain of that. He’d play with my son Eric and my son Donald and he’d just play with them forever.”

Trump and Jackson at the Taj Mahal hotel casino in April 1990

In February 2016, Trump was criticised by Jermaine Jackson after claiming Michael lost self-esteem due to “bad surgery”.

Trump said: “He lost tremendous confidence because of, honestly, bad-bad-bad surgery. He had the worst. He had people that did numbers on him that were just unbelievable. Believe it or not, when you lose your confidence in something, you can even lose your talent."


Read next: The story behind Michael Jackson's Ghosts


But Trump also paid tribute to his friend. “He was an amazing guy, but beyond all else, he was the greatest entertainer I've ever known,” he said. “He had magic. He was a genius. He was also a really good person, and when you got to know him, you realized how smart he was. He was brilliant.

“Now, Michael wasn't the same Michael for the last 10 years. He was not well. He had a lot of problems, a lot of difficulties. He was embarrassed by it. He was embarrassed by what was happening to him.

“But he's not going to be remembered for the last 10 years; he's going to be remembered for the first 35 years. Michael in his prime — there's never been anybody like him.”

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