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Bill Gates may not be the squeaky clean nerd we thought

Strippers, affairs, private jets, secret clubs, weekend retreats with ex-girlfriends, bitter business feuds, naked pool parties: inside the hidden life of Bill Gates.

Bill Gates now (main picture) and in his younger years, flipping a floppy disk of the first version of Windows. Pictures: AFP/Supplied
Bill Gates now (main picture) and in his younger years, flipping a floppy disk of the first version of Windows. Pictures: AFP/Supplied

Over the course of their long and rocky relationship, Steve Jobs frequently mocked Bill Gates, painting the Microsoft mogul as a dreary and narrow-minded drone with no idea of how to cut loose. “He’d be a broader guy if he had dropped acid once or gone off to an ashram when he was younger,” Jobs said of him, according to Walter Isaacson’s 2011 biography of the Apple co-founder.

Jobs knew Gates fairly well, but on that point he may have misjudged his man. Gates did drop acid when he was younger (or so he has strongly implied), and his recently announced mega-divorce from Melinda French Gates has focused attention on the surprisingly decadent life of the world’s most famous geek.

Strippers, affairs, private jets, secret A-list clubs, weekend retreats with ex-girlfriends, bitter business feuds, driving offences, naked pool parties and a little-known connection to Jeffrey Epstein: the hidden life of Bill Gates reveals a much livelier and loucher character than his cuddly-nerd public persona. Turns out there’s more to Gates than software and philanthropy.

The Epstein connection has raised questions about Gates’s judgment. According to The Wall Street Journal, the pair’s relationship began in 2011, several years after Epstein was jailed for 13 months for soliciting prostitution from under-age girls.

Fury over Epstein

Melinda is reported to have been furious with her husband for meeting the convicted sex offender and, according to the Daily Beast website, the friendship was a “turning point” in the couple’s relationship. The Gates-Epstein connection became public at about the time of the financier and sex offender’s downfall in 2019, and Melinda hired divorce lawyers soon afterwards.

Gates insists he was not friends with disgraced Jeffrey Epstein (pictured). Picture: Palm Beach County Sheriff's Department / AFP
Gates insists he was not friends with disgraced Jeffrey Epstein (pictured). Picture: Palm Beach County Sheriff's Department / AFP

Gates, 65, has insisted that he was not friends with Epstein, stating that their connection was based on philanthropy. “Every meeting where I was with him were meetings with men,” Gates said in a statement. “I was never at any parties or anything like that.” His spokeswoman, Bridgitt Arnold, said he “regrets” meeting Epstein and acknowledges that it was an “error in judgment”.

Relationships on skids

The end of Bill and Melinda’s 27-year marriage isn’t the only close relationship in Gates’s life to have hit the skids over time. His closest friend from school was Paul Allen, another tech wizard, with whom he co-founded Microsoft. Together the pair built a world-changing behemoth.

Yet in 1982, when Allen was diagnosed with Hodgkin’s lymphoma, he temporarily stepped back from Microsoft to focus on his treatment. The relationship between the two men had been in decline for some time, but on returning from illness Allen discovered Gates plotting to dilute his shares in the company. “This shows your true character once and for all,” Allen raged at Gates, later resigning from Microsoft. He described the fallout as being “like a failed romance”.

Gates has acknowledged that he can be an explosive character to work with. He once told Playboy magazine that he would often say to colleagues in meetings, “That’s the dumbest idea I have ever heard.”

Slick PR team

Gates has always carefully controlled his public image, particularly in his later years, when his focus has been on the Bill & Melinda Gates Foundation, believed to be the world’s largest private foundation, with an endowment of almost dollars 50 billion. He has a large and slick PR team and has been legacy-hunting of late, participating in a hagiographic four-part Netflix series, Inside Bill’s Brain.

The exterior of the Bill and Melinda Gates Foundation in Seattle, Washington. Picture: David Ryder/Getty Images/AFP
The exterior of the Bill and Melinda Gates Foundation in Seattle, Washington. Picture: David Ryder/Getty Images/AFP

Things were a little wilder in his youth, though, when computer wizardry and its attendant riches were a means of attracting female attention. On his website Gates recounts how, as a pupil at the elite Lakeside School in Seattle, he used his programming skills to write the class timetables, modifying the code so that he was in classes with “interesting girls”.

According to a biography by James Wallace, during Gates’s two years at Harvard, before he dropped out to set up Microsoft, he liked to “frequent Boston’s notorious Combat Zone, with its porn shows, strip joints and prostitutes”. In his Playboy magazine interview from 1994, Gates acknowledged that there were “things I did under the age of 25 that I ended up not doing subsequently”. “Ever take LSD?” the interviewer probed. “My errant youth ended a long time ago,” was Gates’s evasive response.

Bill’s party trick

Gates started going out with Melinda French, a Microsoft employee, in 1988. According to Wallace, he used his party trick of jumping over a table, “a feat that he had enjoyed performing in female company for many years”, to woo the keen runner and hiker.

Bill Gates shares the stage with his wife Melinda in 2014. Picture: Justin Sullivan/Getty Images/AFP
Bill Gates shares the stage with his wife Melinda in 2014. Picture: Justin Sullivan/Getty Images/AFP

Yet even as the pair drew close, Gates “continued to play the field for a while, especially when he was out of town on business”, Wallace writes in Overdrive: Bill Gates and the Race to Control Cyberspace. He recounts how Gates would “frequently hit on” female journalists who covered Microsoft and the technology industry.

“The computer industry doesn’t have groupies like rock [music] does,” Gates told Playboy. Yet Wallace claims that newspaper reporters went easy on Gates because Microsoft “spoon-fed” them stories and they didn’t want the flow of information to end. “They also didn’t report on the wild bachelor parties that Microsoft’s boyish chairman would throw in his Seattle home, for which Gates would visit one of Seattle’s all-nude nightclubs and hire dancers to come to his home and swim naked with his friends in his indoor pool,” Wallace writes.

Old flames

According to Wallace, French was “well aware of Gates’s womanising and consequently the relationship ran hot and cold. At one point they broke up for nearly a year, reportedly because Gates refused to make any kind of commitment.”

Before he married French in 1994, Gates called an old flame, Ann Winblad, to ask her permission. The pair had remained close after breaking up the previous year. Winblad gave her blessing, but she and Gates continued to holiday together annually at a beach bungalow in North Carolina, where Gates has said they would “play putt-putt [mini golf] while discussing biotechnology”. Or, as Winblad put it: “We can share our thoughts about the world and ourselves.” Melinda reportedly gave this unusual arrangement her blessing.

Gates has become famous for his enormous donations to medical causes, most notably the fight against malaria in Africa. In the past 18 months he has also played a key role in the fight against the coronavirus, spending millions on vaccine development. He’s not averse to more frivolous expenditures, though.

Xanadu 2.0

At his vast waterfront home in Medina, Washington, known in the media as Xanadu 2.0, the regularly refreshed sand for his private beach is transported from the Caribbean island of St Lucia on a barge. He has spent more than $US30 million on paintings by Leonardo da Vinci and Winslow Homer. On the ceiling of Gates’s Xanadu library is a quote from The Great Gatsby: “He had come a long way to this blue lawn, and his dream must have seemed so close that he could hardly fail to grasp it.”

Bill Gates' Washington home on the Pacific coast. Picture: Cutler Anderson Architects.
Bill Gates' Washington home on the Pacific coast. Picture: Cutler Anderson Architects.

Despite being deeply troubled by climate change — he recently published a book on the subject, How to Avoid a Climate Disaster — Gates travels the world by private jet. In 1994 he boasted to Playboy that not having a private plane helped to keep him normal. “You can get used to that kind of stuff, and I think that’s bad,” he said. “It takes you away from normal experiences in a way that is probably debilitating.” Yet when he attended the Paris climate change conference in 2015, Gates flew private. He’s certainly sensible to avoid driving too often: he has twice been arrested for driving without a licence, once while speeding, the other time while running a red light.

Bill Gates private jet parked on tarmac of Hamilton Island as he holidayed on Hayman Island in 2000. Picture: David Sproule
Bill Gates private jet parked on tarmac of Hamilton Island as he holidayed on Hayman Island in 2000. Picture: David Sproule

Gates has said repeatedly that he plans to leave only a tiny sliver of his fortune, as little as $US10 million each, to his children, Rory, Phoebe and Jennifer. But he’s not averse to bestowing the odd gift on them from time to time: when Jennifer graduated from Stanford, Gates presented his equestrian-loving daughter with a 124-acre horse farm in the hills of North Salem, New York, valued at $US15 million.

A-list bolthole

In his later years Gates has increasingly mingled with fellow A-listers. According to the New York Post, he has spent the past few months “holed up” at the ritzy Vintage Club, a golf resort in Indian Wells, California, which has a $US250,000 joining fee. The Post reports that he has told golf buddies there that his marriage has been “loveless” for some time.

Another asset that Bill and Melinda will have to split is their luxurious home in the members-only Yellowstone Club in Big Sky, Montana, an exclusive golf and skiing resort where their neighbours include the American football player Tom Brady and his wife, the supermodel Gisele Bündchen, the pop star Justin Timberlake and, for a while, the actor Ben Affleck and his wife, the actress Jennifer Garner.

The rakish Affleck shocked the world last week when it was revealed that he had returned to his ex-girlfriend, Jennifer Lopez, after breaking up with Garner. Perhaps the Batman star can give Gates tips on how to navigate life as a wealthy divorce. Though if Gates’s early years are anything to go by, he may not need them.

The Times

Bill and Melinda Gates, with their family. Picture: Supplied
Bill and Melinda Gates, with their family. Picture: Supplied

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Original URL: https://www.theaustralian.com.au/world/the-times/bill-gates-may-not-be-the-squeaky-clean-nerd-we-thought/news-story/fe0d77f80571db71c4fdb06ac2900b2f