AC72's America's Cup Quest
Credit: Photograpg by Jose Mandojana

On a sunny Tuesday last October, Oracle Team USA were taking their new sailboat out for a spin. The boat – a 72-foot wing-sail catamaran called an AC72, funded by software billionaire Larry Ellison – had been engineered over hundreds of thousands of man-hours to be one of the fastest, most expensive sailing vessels ever built. It cost more than $10 million and could sail twice as fast as the wind. As the hosts and defending champions of the America's Cup – the oldest international athletic competition in the world, the 34th installment of which will take place in September in San Francisco – Oracle were the favorites to capture the trophy. The AC72 was the boat that would take them there.

UPDATE: How Team USA Won the America's Cup

The boat docked off from Oracle's home base into the chilly waters of San Francisco Bay. Among the 11-man crew were some of the most accomplished sailors in the world, including an Olympic gold medalist and seven previous America's Cup winners. But the boat was a radical new design, and just a few dozen people in the world had ever sailed it. Today was Oracle's eighth day on the boat; so far they'd been on the water less than 40 hours, not even a full workweek.

The AC72 is a monster of a boat. Its mast stands more than 13 stories tall, and its rigid carbon-fiber wing is larger than a Boeing 747. It is a sailboat the same way the Batmobile is a car. As recently as 2007, America's Cup boats were still traditional-style monohulls, the kind of majestic-looking yacht you probably picture when you think of the Cup – like Ted Turner's Courageous, or Dennis Conner's Stars & Stripes. But in the past few years, Ellison and his mega-wealthy rivals have poured hundreds of millions of dollars into cutting-edge boat technology that has reshaped and revolutionized the nature of sailing itself.

By just after 3 p.m., the wind was blowing at 25 knots, higher than the Cup's safety limits. The tide was also one of the biggest of the year so far – taken together, these were "extreme conditions," says Oracle's skipper and helmsman, Jimmy Spithill, who is not prone to exaggeration. Spithill decided to head back to the shelter of the South Bay, where the weather would be calmer. But he is also an adrenaline junkie who has flown with the Blue Angels and ridden a Ducati at nearly 150 mph. First, he wanted to make one last run.

The boat tacked upwind, curling past Alcatraz and toward the massive shoulders of the Golden Gate Bridge. By now the wind was gusting at nearly 30 knots, and the tide was at max ebb, sucking water out of the bay at an alarming rate. The two forces, wind and water, combined to create a massive chop. "We pretty much couldn't have picked a worse day," says Dirk de Ridder, the man responsible for trimming Oracle's massive sail. "It was a really nasty trip."

"When we put it in," recalls Spithill, "we were right on the edge." The boat was attempting a tricky maneuver called a bear away, in which it would turn downwind, across the roiling waves. Rome Kirby – at 24, the second-youngest sailor on the team, who had been with Oracle for only three months – was in one of the front cockpits with three other sailors when they began the turn. "All of a sudden the breeze kicked in, and it was like, man," Kirby says. "And then it just dug in."

The boat's starboard bow burrowed into the water, kicking the stern straight up into the air. It's called pitchpoling – basically a somersault that sends the boat tumbling wildly bottom up. The port-side stern flipped, as well, and in an instant, Spithill lost all ability to control the boat. "We didn't have a chance," de Ridder says. "Past the point of no return."

"Once you feel that bow start to drop, all you can do is white-knuckle it," says Jono MacBeth, who was in one of the boat's eight cockpits. All the teams in the America's Cup built their boats according to the same basic design parameters, but within that, there's room for a near-infinite number of tweaks and variations. Oracle were the only team to build their boat with cockpits – waist-high cubbyholes in which the sailors could hunker down. The idea was to reduce wind resistance, to make the boat more aerodynamic. But right now, they were lifesavers, keeping the sailors from being flung overboard. "We were just hanging on," says MacBeth.

Tom Slingsby was in one of the rear cockpits, right behind Spithill. He didn't realize what was happening until it was too late. "I had my head down, so I didn't notice until we were about 30 feet in the air," he says. "Then, all of a sudden, we were 65 feet up." Slingsby was thrown from the cockpit and landed on top of Spithill, who was clinging to the boat's steering wheel. With that extra half-second delay, Slingsby managed to grab hold of a winch and pull himself back in.

Meanwhile, Joey Newton was at the very front of the boat, on the trampoline-like platform that stretches between the boat's two hulls. "We hadn't had a big scare yet, so I wasn't harnessed in," Newton says. As the boat started to nose-dive, a wall of water came rushing at him at 40 miles an hour, washing him halfway off the boat before Kirby grabbed him and dragged him back on.

At this point, the boat had come to a stop fully perpendicular to the water, the tip of the mast propping it up like a giant easel. Two of the sailors dangled from the net by their fingers; in the front cockpit, 20 feet in the air, Kirby and Newton were deciding whether to jump.

It was not a minor question. The boat was outfitted with a pair of 10-foot-long daggerboards, razor-sharp carbon blades that maintain stability in the water. Fall on one from 20 feet up, and a sailor could end up sliced in half. There was also the matter of the hollow wing, and whether it would hold under the pressure of the seven-ton boat. If it were to snap as they were jumping in, the boat could collapse on top of them, knocking them unconscious, crushing them, or, maybe worst of all, trapping them underneath. "Imagine being under a net in San Francisco Bay, cold, stressed, and out of breath," de Ridder says. "No chance."

Behind them, MacBeth said they needed to quit stalling, because he was next in line. Newton and Kirby jumped, and one by one, the rest of the crew climbed the 40 or 50 feet down through the cockpits and carefully followed suit.

Spithill says that between the moment he thought they might capsize and the moment he knew they definitely were capsizing was "a split second." "It's kind of like a race car, when they're right on the edge, and then you hit the wall," he says. "It's not a lot of time. But at the end of the day," he adds, "responsibility lies with me. It was my mistake. We were pushing too much."

The America's Cup encourages that kind of risk-taking. If you still think of sailing's most iconic race as guys named Thurston tooling around Newport in navy blazers and Top-Siders, a glass of bubbly in hand – it might be time to reassess. Today's America's Cup is faster, more punishing, and more dangerous than ever, pushing the very frontiers of speed. The boats are almost too powerful for their own good, like seven-ton bucking broncos, while the sailors, clad in body armor and crash helmets, look less like weekend yacht-clubbers than test pilots at the X Games. It's all part of Ellison's plan to attract a bigger audience, to sell the sport to fans weaned on car crashes and video games. "It's a completely different type of racing than any of us are used to," says Ben Ainslie, Oracle's second helmsman. "Jimmy described it as going to the moon for the first time. No one's ever done it before – we don't actually know where the limit is."

After all of Oracle's sailors had been accounted for, the next step was to try to save the boat. The wing and most of the hull were still intact, but the tide was dragging them out to sea at 600 feet per minute. By the time they towed it back to the dock at 1 a.m., it had been swept out to the ocean, four miles past the Golden Gate, and was badly damaged. They spent the next several weeks going over the crash in second-by-second detail, developing a plan in case it happened again. "Having said that," Newton says, "I'm sure we haven't seen the last capsize in an AC72."

His words would prove prophetic. Seven months later, the Swedish America's Cup team, Artemis Racing, capsized in the San Francisco Bay less than a mile from where Oracle went down. One of their sailors, Andrew "Bart" Simpson, an Olympian from England, was trapped under the wreckage and wasn't discovered for 10 minutes. The cause of death is still being determined.

Back in October, though, barring some scrapes and bruises, everyone on Oracle's boat was OK. "We were incredibly lucky," Newton says. "A capsize like that, you'd be lucky not to maim or even kill someone, and we got away without a scratch. I don't know how many times you could do that again with the same result."