That same year, Gates was memorably hit in the face with a cream pie in Brussels. “He could have been a utopist, but he prefers being the lackey of the establishment,” his prankster assailant claimed. “The attack against him is symbolic, it’s against hierarchical power itself.”

Gates flubs his Congressional testimony

The culmination of the Microsoft antitrust concerns was a Congressional hearing in 1998. Gates notoriously flubbed his testimony, coming off as smug and arrogant in his deposition and bickering over the definition of words like “concerned.”

“He looked bad, there’s no question. He didn’t look truthful. He looked calculating, and I think that probably both damaged Microsoft’s public image and influenced” the judge in the antitrust case, DOJ antitrust acting assistant attorney general Doug Melamed told The Ringer. Gates himself later told the New Yorker that he “regretted ‘taunting’ regulators.”

Federal district judge Thomas Penfield Jackson ordered that Microsoft be split into two in 2000, but the decision was ultimately overturned on appeal, and Microsoft lost its dominance anyway as new behemoths like Google began their ascent.

Gates’ reputation as an office bully

Reports of Gates’ behavior as a young boss and colleague were frequently unflattering. “He’s a brilliant businessman,” New Yorker writer Ken Auletta, who wrote the book World War 3.0: Microsoft and Its Enemies, said in a 2001 PBS News Hour interview. But Auletta went on to paint a portrait of Gates as an immature tyrant:

[I]n many ways he’s a child. He’s asocial. And he behaved, he behaves like a child sometimes does when they’re upset. They have a tantrum. He has tantrums.

Some of Gates’ colleagues also have portrayed him as a hot-tempered bully prone to swearing in meetings and berating employees in so-called “flame mails,” late-night messages containing lines like “This is the stupidest piece of code ever written.” Gates would go to the company parking lot on weekends to see who’d come into work—“I knew everyone’s license plates so I could look out in the parking lot and see, when did people come in, when were they leaving,” he admitted in a BBC Radio 4 interview on the program Desert Island Discs.

According to Gates’ co-founder, he could be a schemer, too. In Allen’s 2011 memoir The Idea Man, Allen writes that while he was recovering from Hodgkin’s lymphoma, he overheard Gates talking with Microsoft’s then-business manager Steve Ballmer. Gates was complaining about Allen’s lack of productivity and wanted to dilute Allen’s equity in the company. “I helped start the company and was still an active member of management, though limited by my illness, and now my partner and my colleague were scheming to rip me off,” Allen recalls. (He and Gates reconciled before Allen’s death in 2018.)

Gates’ golden years

Gates rebranded himself in the post-DOJ lawsuit years. He stepped down as Microsoft CEO in 2000 and increasingly devoted himself to philanthropy, winning accolades (including a 2005 Time magazine cover as a “Good Samaritan” and Person of the Year) for his work on global public health and economic development. Auletta told the Times in 2014 that while the sheer size of Gates’ charitable donations indicated that he was motivated by more than improving his image, his efforts “became part of Microsoft’s PR effort to humanize Gates.”

Critics sometimes raised concerns about the foundation’s efficacy, focus, and outsize influence. But these were typically drowned out by positive press. The Giving Pledge, which Gates launched with Warren Buffet in 2010 in an effort to convince billionaires to donate at least half their wealth, further burnished Gates’ image as a philanthropist.

Now it seems the shine is once again coming off Gates’ reputation. It’s a reminder of the ways that philanthropy can be used to deflect scrutiny—and the dangers of putting anyone, particularly extremely wealthy and powerful individuals—on a pedestal.

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