Larry Ellison once spied on Bill Gates' Microsoft. Now he is the second richest man: Is this the ultimate revenge?
When Silicon Valley stories are told, the rivalry between Steve Jobs and
Bill Gates
often takes the spotlight—two visionaries locked in a dramatic dance of respect, competition, and reinvention. But there's another tech feud that simmered with far more intensity and far less grace:
Larry Ellison
vs. Bill Gates. Nearly 50 years after Ellison co-founded
Oracle
, 2025 may be the year he finally got his revenge.
While Jobs and Gates shared a history of mutual admiration despite business clashes, Ellison and Gates operated from a very different playbook. As Oracle went head-to-head with
Microsoft
in the database and
cloud computing
space, the competition became deeply personal for Ellison, who once bluntly stated, 'It's not enough that we win; all others must lose.'
A Rivalry Rooted in Aggression, Not Admiration
According to a report by Barchart, Ellison was long irritated by what he saw as Microsoft's underhanded market strategies—undercutting prices, bundling products, and squeezing out competition. Unlike his more diplomatic peers, Ellison didn't shy away from going public with his distaste.
'Well, what's new is nothing's new,' he said in a now-iconic rant reported by Business Insider. '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.'
For Ellison, this wasn't just about business tactics—it was about principle, and he made it clear that he viewed Gates' leadership as the embodiment of corporate opportunism.
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— seanpk (@seanpk)
From Spreadsheets to Surveillance: The Trashgate Episode
The rivalry hit its most bizarre peak in the early 2000s with a scandal now remembered as Trashgate. Oracle suspected that Microsoft was covertly funding academic groups and think tanks to manipulate public and regulatory opinion. In response, Ellison hired a PR firm to dig up evidence—literally. The firm, in turn, employed private investigators to rummage through the trash of buildings tied to Microsoft.
Critics called the move absurd, unethical, and bordering on corporate espionage. But Ellison was unfazed. 'All we did is try to take information that was hidden and bring it to light,' he said. 'I don't think that was arrogance. I think it was a public service.' To him, this wasn't a smear campaign—it was a counterstrike in a war Microsoft had started.
— sandykory (@sandykory)
The 2025 Reality: Ellison's Triumph Over Gates
Fast forward to June 2025, and Ellison may finally be having the last laugh. According to Forbes' real-time billionaire list, Larry Ellison is now the second-richest person in the world, with a staggering net worth of $254 billion—second only to Elon Musk. In a twist of fate, Ellison's fortune now more than doubles that of Bill Gates, who has vowed to give away his wealth in his lifetime and owns less than 1% of Microsoft today.
The secret behind Ellison's explosive financial rise lies in Oracle's booming presence in AI. Since 2023, his net worth has more than doubled—up from $107 billion—thanks to Oracle's aggressive AI strategy and his commanding ownership stake. He currently controls about 40% of
Oracle
, far more than Jeff Bezos's 10% share in Amazon or Mark Zuckerberg's 13% in Meta.
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While Microsoft remains the world's most valuable company, according to CompaniesMarketCap, the symbolic win seems to have swung in Ellison's favour. Oracle may be ranked only 16th in valuation, but Ellison now holds far greater individual power, wealth, and ownership than his longtime rival.
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