Allen, 51, is known for indulging his enthusiasms with more zest than sensibility. He owns both of the Northwest's underperforming professional teams, the football Seattle Seahawks and basketball's Portland Trailblazers, and bankrolled the Experience Music Project-a Frank Gehry-designed museum-cum-technological marvel that includes a giant walk-through of Jimi Hendrix's guitar and a Sky Church for rockers. He plays electric guitar (when not smashing it, a la Jimi), sometimes on board his 199-foot Feadship Meduse, which has an onboard recording studio. He's ranked seventh in the latest Forbes 400, two places ahead of the 60-year-old Ellison, whose stock took a tumble when the IT bubble burst and who has also had to navigate through the choppy waters that surrounded his third divorce. Ellison, whose abiding ambition is to drive Oracle above Microsoft as well as springboard ahead of Allen in the Forbes list, did have the consolation of bettering his rival in the 2003 America's Cup in New Zealand.
Ellison and Oracle mounted a traditional syndicate approach to the Cup. Allen, however, came to the world's most exclusive competition by accident-stepping in to support the Seattle-based OneWorld group when founder Craig McCaw found himself overextended. Along with the Cup team, Allen inherited the McCaw-commissioned 301-foot Tatoosh. For Allen, the Cup experience proved to be a familiar fizzle-first with accusations of design espionage prior to his takeover, followed by a humiliating defeat at the hands of Ellison's Oracle BMW in the semifinals of the Louis Vuitton Challenger series.
But though Allen has since dropped out of the America's Cup scene, he did find his bliss-and a winner-backing Burt Rutan's SpaceShipOne, which won the $10 million Ansari X prize last October for the first privately funded spacecraft to reach 330,000 feet and return to land. Ellison, meanwhile, has been busy reconfiguring his San Francisco-based America's Cup team for a second tilt at the trophy, to be sailed off Valencia in 2007.