The book covers the quest of Larry Ellison to win the America's Cup yachting trophy, his establishment of Oracle Team USA under the banner of the Golden Gate Yacht Club, and his various Cup campaigns, at the 2003, 2007 and 2010 Cups. And at the 2013 Cup in the second edition. The book opens with Ellison's experiences at the catastrophic 1998 Sydney to Hobart yacht race, where a freak storm with hurricane force winds sunk several yachts, killing several sailors. Ellison vowed to transition from open water racing to inshore racing, and in that, go after the oldest trophy in international sport, the America's Cup. Basing out of San Francisco, it covers his troubles with the high brow St. Francis Yacht Club, leading to a search for an alternate sponsoring squadron. In conjunction with this search, the election of a new commodore at the Golden Gate Yacht Club, a club with middle class blue collar membership, lead to Norbert Bajurin, a car radiator shop owner and mechanic, winning. Bajurin discovered the financial difficulties of the Golden Gate Yacht Club, and sought Ellison to be their sponsoring yacht club in a Cup campaign, solving the pending insolvency of his beloved squadron. Then, covering the partnership between the billionaire and the mechanic, and the establishment of Oracle Team USA at the Golden Gate Yacht Club. The book then follows the unsuccessful cup campaigns at the 2003 and 2007 America's Cups, which resulted in their failure to become the US entry into the Cup. Then their rogue challenge, under the Deed of Gift, in the 2010 Cup, becoming the challenger against the Cup defender, and winning the Cup. In the expanded second edition, it follows on the successful Cup defense in the 2013 Cup, and their comeback from the brink of losing the Cup in 2013.