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The oldest trophy in international sport, the America’s Cup race, predates the modern Olympics and remains the most prestigious honor in sailing. Named for the schooner America, which outran an entire fleet of British ships around the Isle of Wight in 1851, the event has been held 31 times since then.

Although American teams traditionally dominate the Cup, recent winners include teams from Australia, New Zealand, and Switzerland. While the race location was still being battled out in the courtroom as of press time (right now it’s set for Valencia, Spain, but it could move to Ras al-Khaimah in the United Arab Emirates), beginning February 8, U.S. team BMW Oracle Racing will challenge the current defending champion, a Swiss syndicate named Alinghi , for the 33rd Cup . The epic battle will be broadcast live to billions around the globe.

The America’s Cup is not sailing for weekenders; it is extremely specialized, high-performance racing that uses carbon-fiber boats packed with electronics and designed to cruise at over twice the speed of the wind. Crews spend months and even years configuring and inventing new technologies to beat the competition. BMW Oracle Racing’s sail, for instance, is the world’s largest ever at 6,800 square feet — that’s 80 percent larger than a 747 wing. And for the first time in Cup history, organizers will allow both the Alinghi and BMW Oracle Racing team boats to use motorized engines to trim the sails and move water ballast.

The Cup has often been the exclusive province of rich industrialists, from Sir Thomas Lipton (of the Lipton tea fortune) to media mogul Ted Turner. Preparations are absurdly competitive, with teams habitually buying and selling boats and hiring and firing captains and crews . Squadrons of lawyers also can become involved — some Cup results have even been decided by court judgment.

The 2010 race is no exception. Archrivals BMW Oracle Racing and Alinghi both boast skippers from New Zealand who once raced on the same team. Both team owners were once good friends. And both have spent record amounts of money in order to win. Here’s how the 33rd America’s Cup participants compare.

BOR 90
90 feet LENGTH 90 feet
185 feet MAST HEIGHT 180 feet (estimated)
1 hard-surface “wing” NUMBER OF SAILS
3 (trimaran) NUMBER OF HULLS 2 (catamaran)
Carbon fiber and Kevlar, covered with aeronautical shrink film SAIL MATERIAL 3DL laminated blend of Mylar yarn and Kevlar
November 10, 2009 (with new “wing” sail) SAILED FOR THE FIRST TIME July 20, 2009
At least $10 million BOAT COSTS Estimated $9.9 million
Sir Russell Coutts (New Zealand native, won America’s Cup three times, formerly with Alinghi) BOAT CAPTAINS Brad Butterworth (New Zealand native, member of America’s Cup winning team four times)
Larry Ellison (American billionaire, Oracle software; Forbes world wealth rank: 4; personal wealth: $27 billion) FINANCIERS Ernesto Bertarelli (Swiss/Italian billionaire involved in pharmaceuticals and biotech; Forbes world wealth rank: 52; personal wealth: $8.2 billion)
Afterguard/founder FINANCIER’S TITLE Runner/grinder/president
Louis Vuitton Cup 2007 — lost to Luna Rossa Challenge in semifinals
Louis Vuitton Pacific Series 2009 — lost to Alinghi in semifinals
COMPETITION HISTORY America’s Cup winner 2003, 2007 Louis Vuitton Cup winner 2003 (beating BMW Oracle in final)
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