In the fall of 2000, Fortune found Larry Ellison holding court at Oracle’s glittering Redwood Shores campus—seated, pointedly, in the office of Ray Lane, the company’s recently ousted president. The message was pure Ellison: No one is irreplaceable. Except, of course, Larry himself.
The article’s headline “The next richest man in the world” sets up a clear contest between Ellison and the man then in that top spot: Microsoft cofounder Bill Gates. Ellison aspired to make Oracle into something like the new version of Microsoft. Ellison admitted to Fortune that he hired private investigators to dig through Microsoft’s trash for damaging documents: “Unsavory, yucky—kind of,” he told Fortune’s Andy Serwer. “But legal.”
The Gates-Ellison rivalry was always more than a wealth contest. It was a clash of archetypes—the disheveled Seattle nerd versus the California playboy. Gates built Microsoft with methodical, product-driven precision. Ellison ran Oracle like a pirate ship, “going through wives and top executives like pairs of boots,” as Serwer wrote. His old pal Andy Grove, then Intel’s CEO, told Fortune that Ellison “works very hard at his bad-boy image.”
What’s remarkable in hindsight is that both Ellison and Gates were right about the future—just on different timelines. Gates correctly bet on software as the center of the computing universe. Ellison correctly bet that integrated enterprise applications would reshape corporate America. He just underestimated how hard the pivot would be.
Who ultimately won is hard to determine: Gates slipped away into massive-scale philanthropy before the final scoreboard was posted, becoming an elder statesman on a global scale. Lately, though, he has not appeared in public outside of his foundation, since the latest DOJ Epstein drop included embarrassing revelations about him.
Ellison kept fighting, becoming a bigger, richer, older bad boy. He acquired Sun Microsystems, rebuilt Oracle around the cloud, and is now one of the defining financiers of the AI era, with a close relationship with President Donald Trump. His fortune has multiplied many times over since that 2000 profile, and he recently backed his son’s bid to overhaul Hollywood with Paramount’s acquisition of Warner Bros.
What really drives Ellison? Perhaps the most apt answer is the one found in that quarter-century-old article: “When Apple founder and CEO Steve Jobs (whom Ellison repeatedly refers to as his best friend) is asked what he thinks is the driving motivation of his pal, he chuckles, thinks for a moment, and then whispers into the phone: ‘Rosebud.’”
