Bill Gates is one of the most consequential figures in the history of personal computing — and for Apple fans, one of the most complicated.
As the co-founder of Microsoft, Gates built the company that would become Apple’s fiercest rival through the 1980s and ’90s. Microsoft’s Windows operating system rose alongside the IBM PC, eventually dominating the market Apple had helped create with the Apple II and Macintosh.
Tensions flared early, especially after Apple accused Microsoft of copying elements of the Macintosh graphical user interface for Windows. Yet Gates and Steve Jobs shared a long, intertwined history: from Microsoft writing software for the original Mac to their famous onstage conversation at the 2007 D5 Conference, where the two reflected — sometimes sharply, often warmly — on decades of rivalry and innovation.
For Apple loyalists, one of the most unforgettable moments came in 1997, when a struggling Apple accepted a $150 million investment from Microsoft. Gates appeared via satellite at Macworld Boston, looming on a giant screen behind Jobs, announcing continued support for Microsoft Office on the Mac. The crowd famously booed, but the deal helped stabilize Apple at a pivotal moment, buying time for Jobs’ turnaround that would eventually lead to the iMac, iPod, iPhone, and beyond. In that sense, Gates played an indirect but meaningful role in Apple’s survival story — an irony not lost on longtime observers of Silicon Valley’s most storied rivalry.
In recent years, however, Gates’ legacy has grown more complicated. His long association with convicted sex offender Jeffrey Epstein drew widespread criticism, particularly after Epstein’s 2019 arrest and death. Reports revealed that Gates met with Epstein multiple times after Epstein’s 2008 conviction, leading to public scrutiny and reputational damage. While Gates has said he regrets the meetings and characterized them as a mistake, the controversy has undeniably cast a shadow over his later-life image — a reminder that even towering figures in technology are not immune from personal and ethical controversies that reshape how history remembers them.
May 26, 2010: In a massive milestone, Apple passes Microsoft to become the world’s most valuable technology company for the first time.
The changing of the guard proves particularly amazing given that, just 15 years earlier, Apple looked close to dead, while Microsoft dominated the tech world thanks to Windows 95.
May 12, 2005: Longtime Apple frenemy Bill Gates tells a German newspaper that Apple may have hit it big with the iPod, but that its success isn’t going to last forever.
The reason for the Microsoft co-founder’s doomy take on the iPod’s future? He thinks mobile phones will steal the music player’s market share.
The good news for Gates is that he was right on the money. The bad news for Microsoft is that Apple cannibalized itself by making the iPhone. And Apple’s smartphone became even more successful than the iPod.
April 4, 1975: Microsoft is founded by childhood friends Bill Gates and Paul Allen. The software company destined to become a tech behemoth — and a major Apple frenemy.
A few years later, Microsoft will break through to the mainstream with Excel and Word, becoming a key developer of Macintosh software. Then comes the Windows operating system, looking suspiciously Apple-like. After Windows arrives, Microsoft and Apple will embark upon a long-running feud.
March 17, 1988: Apple sues Microsoft for allegedly stealing 189 different elements of its Macintosh operating system to create Windows 2.0.
The incident, which causes a deep rift between Apple and one of its top developers, paves the way for an epic battle between the two companies that will rage for years.
February 11, 2010: With iPad excitement reaching a fever pitch, Microsoft co-founder Bill Gates wades in with his opinion of Apple’s tablet. His view? Apple’s upcoming device is kinda meh.
“There’s nothing on the iPad I look at and say, ‘Oh, I wish Microsoft had done it,'” Gates tells one interviewer.
January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates quits as Microsoft CEO, stepping down just a month after his company’s stock hit its all-time high.
The news coincides with a turning point in the long-running battle between the two tech powerhouses. Microsoft begins a long decline from its previous dominance, while Apple continues its rise to the top.
December 30, 1999: Microsoft hits the height of its 1990s dominance and begins its early-2000s decline, clearing a gap at the top for Apple.
After hitting an all-time high of $53.60, Microsoft stock starts to fall. Less than a year later, MSFT shares will fall more than 60% in value to $20.
November 26, 1984: Microsoft co-founder Bill Gates praises Apple’s newly arrived Macintosh as the future of personal computing.
“The next generation of interesting software will be done on the Macintosh, not the IBM PC,” Gates says in a BusinessWeek cover story.
This high praise for the Mac would seem almost unthinkable coming out of Gates’ mouth just a few years later. However, the interview arrives at a time when Microsoft is best known as one of the biggest Mac developers.
November 21, 1985: Following Steve Jobs’ departure, Apple comes close to signing its own death warrant by licensing the Macintosh’s look and feel to Microsoft. The Apple-Microsoft deal — struck by Microsoft co-founder Bill Gates and Apple CEO John Sculley — comes hot on the heels of the Windows operating system’s release.
The pact gives Microsoft a “non-exclusive, worldwide, royalty-free, perpetual, nontransferable license to use [parts of the Mac technology] in present and future software programs, and to license them to and through third parties for use in their software programs.”
Oh, boy!
August 26, 1991: In their first joint interview, Steve Jobs and Bill Gates trade barbs and debate “the future of the PC” in Fortune magazine.
The spirited discussion marks 10 years since the first IBM PC shipped. The piece also looks at what the future holds for both men — described as the former “boy wonders of computing, now thirtysomething.”
August 21, 2008: Microsoft recruits comedian Jerry Seinfeld for a series of ads. It’s a naked attempt to shake the company’s reputation as a stodgy oldster (as opposed to Apple’s trendsetting hipster image).
Microsoft pays Seinfeld a reported $10 million for the ads. However, thanks to the Mac’s appearance in virtually every episode of Seinfeld over the years, the comedian remains the world’s most famous Apple fanboy.
August 6, 1997: In one of the most famous moments in Apple history, Steve Jobs reveals a $150 million Microsoft investment that saved his company from ruin.
Although often presented as an inexplicable gesture of good faith on the part of Microsoft boss Bill Gates, the cash infusion into Apple actually benefits both companies.
July 25, 1989: Apple suffers a major setback in its copyright-infringement lawsuit against Microsoft for allegedly stealing the Mac’s “look and feel” to create Windows.
Apple sued Microsoft on 189 counts of copyright infringement relating to Windows 2.0.3. The judge overseeing the case throws out 179 of them. This paves the way for Microsoft’s dominance over Apple in the coming decade.
June 25, 1985: Microsoft co-founder Bill Gates sends a memo to Apple execs suggesting that Cupertino should license its Mac operating system and additional technology to other companies.
Apple CEO John Sculley and Macintosh boss Jean Louis Gassée ignore the advice of the 30-year-old Gates, who at the time is best known as a Mac developer. Five months later, Microsoft releases Windows 1.0.
The companies they helped found might have been sworn enemies at times, but Steve Jobs and Bill Gates didn’t hate one another. In fact, as the former Microsoft boss admitted on a recent podcast, he was actually jealous of Steve Jobs.
Appearing on the Armchair Expert podcast, Gates told actor and podcast host Dax Shepard that Jobs was a “wizard” when it came to motivating people. “I was a minor wizard so I couldn’t fall under his spells,” Gates said. “But I could see him casting the spells, and then I would look at people and see them mesmerized … I was so jealous.”
The Gates Foundation, the charitable organization belonging to Bill and Melinda Gates, snapped up more than half a million Apple shares during the first three months of 2020, a new report claims.
According to an SEC filing, reported by Smarter Analyst, the largest private foundation in the world purchased some 501,044 Apple shares in the first quarter of 2020. At present, AAPL is trading at $320.40, having made back the value it lost during the coronavirus pandemic.
Tim Cook isn’t the only tech icon with something big coming out on September 20.
Microsoft co-founder Bill Gates is the subject of a new Netflix documentary series that premieres on iPhone 11 launch day. Inside Bill’s Brain connects chapters of Gates’ personal life with his philanthropic work. Gates does more than other tech luminaries to make the world a better place. Still, he says there’s one skill Steve Jobs possessed that would prove immensely helpful for his current work.
There are plenty of words used to describe Steve Jobs, but “wizard” isn’t one of the ones we hear too often.
That’s exactly what Jobs was, however, according to Microsoft co-founder and long-time Jobs frenemy Bill Gates. Speaking on CNN, Gates said that Jobs accomplished his Apple-correcting wizardry by “casting spells.” But Gates, as a “minor wizard,” was immune to Jobs’ hocus pocus.
Former Microsoft CEO and Steve Jobs frenemy Bill Gates says his company massively missed out by failing to challenge Apple on smartphones.
Describing his “greatest mistake ever,” Gates said the failure to become Apple’s main competitor in the mobile space cost Microsoft $400 billion.
An abandoned 2016 musical about the rivalry between Steve Jobs and frenemy Bill Gates has resulted in the producer being sued for $6 million.
The musical’s producer allegedly told investors he had funding from Microsoft for the project. In fact, the musical was $1 million in debt at the time. It was ultimately canceled just two weeks before it was due to open.
Microsoft co-founder Paul Allen died today after a battle fighting non-Hodgkin’s lymphoma.
Allen was 65 years old and was also the owners of the Seattle Seahawks and the Portland Trailblazers.
The co-founder of Microsoft joined the chorus of voices speaking positively about Apple today. Bill Gates’ relationship with Apple goes back to the very dawn of the company, and he and Steve Jobs were the best of frenemies.
Now that he’s a philanthropist rather the CEO of Microsoft he can speak openly about a former rival.
Bill Gates just got himself a brand new smartphone, and it isn’t an iPhone 8.
The Microsoft co-founder has ditched Windows Mobile for Android. Despite getting closer to Steve Jobs before he died in 2011, Gates still has no interest in using iOS.
Steve Jobs and Bill Gates didn’t always see eye to eye. When it came to their kids’ relationships to technology, however, it seems they agreed on more than they disagreed on.
That’s based on a new interview with Microsoft co-founder Gates, in which he says he and his wife didn’t allow their children to have cellphones until they were 14 — and limited other screen time as well. Jobs did much the same.
President Donald Trump is set to unveil a new government office today that’s tasked with overhauling federal bureaucracies, and he’s asked Tim Cook and other tech leaders for advice.
Even though Trump sparred with Cook on numerous issues during his presidential campaign, the Apple CEO will reportedly lend a hand to the Office of American Innovation. The new office will be led by Trump’s son-in-law, Jared Kushner, and will be tasked with making the country run more like a “great American company.”