World's second richest man once spent billions trying to take down Bill Gates' Microsoft empire
Oracle co-founder Larry Ellison has always been one of the biggest names in the tech world, yet much of his time in the limelight has been spent in opposition to Microsoft's Bill Gates - and he even spent billions of dollars trying to take his rivals down.
When you think of the technology industry's biggest rivalries it's hard not to draw your mind to the several-decade-long conflict between Bill Gates and Steve Jobs, as Microsoft and Apple fought it out to dominate the computing world.
The relationship between the two was often bitter, even in moments when one swooped in to save the other, but they always held a mutual respect for each other's achievements and skillsets that kept their paths intertwined.
You can't necessarily say the same for Larry Ellison's lengthy battle against Gates and Microsoft though, as he went further than most would have even considered in order to ensure Oracle remained on top - and he might just have achieved that feat nearly 50 years after the company was founded.
Why did Larry Ellison hate Microsoft and Bill Gates?
When considering the pure business to business context of Oracle against Microsoft it's easy to understand why there was a rivalry, as both companies competed to win the database and cloud computing war.
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However, the behavior of Gates and his company appeared to get underneath Ellison's skin, with countless reports of undercutting and product bundles in order to squeeze out and win over Oracle's customer base, as per Barchart.
Ellison had a particularly famous rant about Microsoft and Gates, as shared by Business Insider, where he had this to say about his close rival:
"Well, what's new is nothing's new. Microsoft continues to do what they always do, which is to keep the price of Windows high and copy other people's software and just add it to Windows.
"That is the absolute opposite of innovation, and Bill claiming that's innovation, I guess it is innovation in business practice, it's anti-innovation in technology. It's important that everyone understand what Microsoft strategy is."
He also famously declared that "it's not enough that we win; all others must lose," and he showed that best in his attempts to take down Microsoft through brute force.
How did Larry Ellison try to destroy Microsoft?
Billions of dollars were spent in a controversy that has been immortalized now as 'Trashgate', where Oracle and Ellison remained suspicious of Microsoft's alleged funding of academic groups and think tanks in order to influence public perception and regulatory hearings.
This process initially began by hiring a PR firm to investigate and expose Microsoft's 'secret' connections, but things began to escalate when that firm then employed private investigators and detectives to search through the trash of buildings allegedly associated with the tech giant.
Understandably many saw this as a ridiculous, petty, and unnecessary act to one-up his rival, and there were even accusations of corporate espionage which Ellison staunchly denied, illustrating instead that he was performing a 'public service'.
"All we did is try to take information that was hidden and bring it to light," Ellison explained. "I don't think that was arrogance. I think it was a public service."
While both Microsoft and Oracle remain behemoths in the tech industry from a development and financial point of view, Ellison might just have the last laugh in his eyes over his competitors thanks to recent developments.
How rich is Larry Ellison in 2025?
As of June 2025, Forbes' real-time billionaire's list indicates that Larry Ellison has jumped up to become the second richest man in the world, standing behind only Elon Musk with an overall net worth of $254,000,000,000.
This makes him richer than Mark Zuckerberg and Jeff Bezos - but also critically he holds over double the net worth of his long-time rival Bill Gates, although the Microsoft founder has vowed to give away all of his money before he dies.
A bit part of how Ellison has managed to soar so high nearly five decades after he co-founded Oracle is due to the company's leading AI development, and that has allowed his net worth to rise from $107 billion in 2023 to what it is today.
He currently owns roughly 40% of Oracle which is far higher than the relative ownership of competitors like Jeff Bezos, who owns 'just' 10% of Amazon, and Mark Zuckerberg, who holds control of 13% Meta.
Oracle is currently only 16th on the world's most valuable companies according to CompaniesMarketCap, and while Microsoft does currently sit in first place, Gates now owns less than 1% of the company he started back in 1975.