John Kostecki has one instruction for me: “Hold on.” It’s a sunny day in New Zealand’s Hauraki Gulf, off the coast of Auckland, and I’ve just boarded Kostecki’s boat. Actually, calling it a boat suggests something a lot more substantial than what I’m standing on. It’s the barest skeleton of a raft, a wisp of a catamaran 22 feet wide by just under 45 feet long. Called an AC45, it’s a bantam version of the next-generation America’s Cup yacht, and it’s unlike anything else on water. Above me is not a sail but a solid wing, mounted vertically like a fin. At 70 feet tall, it is longer than the wing of a Boeing 727. Yet the craft that this massive airfoil propels is almost fully dematerialized—a CAD file in wireframe hovering over the bay. As far as I can tell, there’s nothing to hold on to.

As the craft bobs idly in the water, Kostecki, the boat’s tactician, motions for me to head out to the center of the netting stretched between the two knifelike hulls, a place where I’m least likely to get in the way. The skipper, Jimmy Spithill, watches silently from behind mirrored sunglasses as I crawl out and embrace the base of the mast. As soon as I’m settled, the three other sailors on board begin to stir their winches. This causes a cat’s cradle of lines to spring up all around me and begin to dance. Just above my head is the wing’s bottom edge, a massive horizontal pole with a half dozen separate lines running in and out of it. It’s like a giant robot’s arm strung with rope tendons, and as it starts to flex—positioning the towering wing to catch the breeze—the boat accelerates with a gut-twisting quickness. Within seconds we’re outpacing the speedboat that dropped me off. A rooster tail of spray shoots from the bow of each hull, leaving me thoroughly soaked.

Next, accompanied by the terrible groaning howl of rope straining under maximum tension, the boat starts to tip up onto its side. One of the hulls lifts free of the water. “Hike out!” Kostecki barks, and the crew races—half running, half speed-climbing—to the high side of the boat. “Sorry, mate,” says one sailor after trampling across my back and flinging himself over the breaching hull. Their weight is the only thing keeping us from flipping. To gain maximum leverage they hang off the boat upside down, facing up, with their feet tangled in the netting and everything past their knees cantilevered over the side. The goal is not to bring our wayward hull back to the water but rather to bring it as close to the surface as possible without touching down. Flying the hull eliminates its drag. Flitting across the water, literally and figuratively on edge, the black carbon-fiber boat takes on a distinctly alien, insectoid grace. The next America’s Cup race takes place in 2013, but one thing is already sure: The event’s pioneers wouldn’t recognize their sport now.

Back in 1851, when the stately yacht America bested the greatest naval power that had ever ruled the seas to win the cup, Queen Victoria, in a bit of stiff-upper-lip hopefulness, famously asked who took second place. “Your Majesty,” the queen’s counselor advised, “there is no second.” And that is really the key to understanding the oldest trophy in international sport. The America’s Cup—the Super Bowl of sailing—is unique among major competitions in that it’s essentially structured as a winner-take-all bet. The grand prize of the America’s Cup race is dominion over the next America’s Cup race. It’s as if the Green Bay Packers were rewarded with not just the Vince Lombardi Trophy but also the NFL. Or if the San Francisco Giants were now in charge of baseball, and not just the Major Leagues but the Japanese and Cuban leagues, too. The team that takes the cup gets nearly complete control over the race, the only caveat being that an official “challenger of record” must agree to the final rules. No wonder the world’s richest men have always been so keen on the contest.

The last cup, in 2010, was a highly contentious battle between Oracle Racing, bankrolled by Oracle CEO Larry Ellison, and Alinghi, the alter ego of the Italian-born Swiss billionaire Ernesto Bertarelli. It marked what may be the nadir of the sport: Alinghi, who won the previous cup, attempted to radically change the rules by using a sham challenger of record. Ellison’s organization sued and won, becoming the official challenger, but as a result the match reverted to the anything-goes rules of the 19th century. Alinghi spared no expense on a specially designed high-speed catamaran. Oracle spared even less expense, devising a paradigm-breaking trimaran with a wing for a sail. Oracle won.

Wing-sail technology carried the day, but the acrimony over the rules seriously tarnished the potential value of Ellison’s prize. Old-line sailors tsk-tsked about the abandonment of the traditional single-hull yacht design. Never before had there been two crass-looking multihulls competing for the America’s Cup. And Ellison’s wing? For traditionalists, it was downright offensive. But even worse for Ellison, the masses—especially the young—tuned out the competition entirely, turned off by the endless lawsuits and massive egos. Facing this reality, Ellison did what any successful businessperson would do after acquiring an underperforming asset: He ordered a shake-up. Instead of bringing back the design rules that had governed the sport for 15 years, Ellison decided to completely reinvent the race. The next America’s Cup will, as Oracle Racing’s CEO Russell Coutts puts it, “meet the expectations of the Facebook generation, not the Flintstone generation.”

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