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First Take: The world's wealthiest underdog

Jon Swartz, USA TODAY 12:38 p.m. EDT September 25, 2013

SAN FRANCISCO – Today may mark the first time in decades the word "underdog" and Larry Ellison appear in the same sentence.

But the Silicon Valley billionaire found himself in that position a few days ago, when his multimillion-dollar Oracle Team USA boat was on the verge of a humiliating loss to Emirates Team New Zealand in the America's Cup.

A win in the decisive race today, though, would cap one of the greatest comebacks in sports history, burnish the athletic resume of Ellison and quite possibly put he and his team in the same conversation as the Miracle on Ice U.S. Olympic hockey team in 1980.

Wait. Larry Ellison?

The Chicago native, who co-founded Oracle and is its CEO, is arguably high-tech's happy warrior, gleefully taking on rivals such as Google, Microsoft and Hewlett Packard while quoting from The Art of War in high-profile smackdowns. While others battle for market share with rivals, Larry's Oracle simply bought PeopleSoft in a hostile takeover several years ago.

His appetite for competition beyond bits and bytes. There was an abortive attempt to buy the Golden State Warriors recently and Ellison still harbors dreams of bringing the NFL back to Los Angeles with a team he blissfully calls the Stars.

Ellison, 69, amassed a personal fortune of $41 billion by treating tech as a form of sport – and the America's Cup is no different. The team got into hot water before it touched San Francisco Bay's cold waters for illegally altering boat parts, costing it valuable points and putting it in a competitive hole.

The cavalier Ellison loves a challenge, however, and his team has clawed back with seven straight wins in the unlikeliest of comebacks.

And he was there to witness both races yesterday: Ellison blew off a keynote speech at the annual Oracle business conference, where some 60,000 people have gathered here this week, to watch history.

The world's wealthiest underdog will have a front-row seat -- on a high-speed chase boat -- to soak it all in today.

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