Inside the Deadly Quest to Win the America’s Cup

Mj 618_348_the edge of the wind
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.”One morning five months after the Oracle crash, Jimmy Spithill gets up at about 5:30 a.m., says goodbye to his wife and two sons (five-year-old Owen and two-year-old Joe), climbs into his car, and drives the seven miles from his home in San Francisco’s Marina neighborhood to Oracle’s home base. The base is located in a run-down warehouse on San Francisco’s Pier 80, an old steel-and-lumber port surrounded by cargo containers and railroad tracks. When the team moved in three years ago, homeless people were squatting nearby. Now the building is protected by a chain-link fence, a security keypad, and closed-circuit cameras.

Spithill is 6-foot-1 and 191 pounds, with close-cropped red hair and lips colored permanently white from sunblock. He’s built like a boxer, and his eyes are like ice. Spithill rides motorcycles and grew up playing rugby, and he can rattle off a lifetime’s worth of injuries: broken ribs, a broken shoulder, a broken collarbone, a broken elbow, a broken leg, and several broken wrists. Surprisingly, he’s never had an injury from sailing.

Spithill attends to team business for about an hour, until the Oracle crew starts to trickle in for the 7:45 a.m. workout. The new boats are so demanding that the sailors have to be in peak physical shape; Oracle’s head trainer, a New Zealander named Craig McFarlane, says they’re fitter than most of the rugby squads he’s trained. They burn three or four thousand calories a day just from sailing, and as many as 9,000 calories in all. During a half-hour race, their heart rates might be at 85 to 95 percent of their maximum capacity the entire time. “You look at the data afterward, and it looks like some of our guys are having heart attacks,” Spithill says. “There’s a lot of fantastic sailors in the world who would never cut it on this boat.”

Today is Tuesday, an intense day. As the Foo Fighters’ “Everlong” plays over the PA, the Oracle’s two 11-man teams split up into groups. The biggest are the grinders: the strongest, burliest guys on the team, responsible for putting out enough torque to control the 3,000-pound wing sail. Their workout today involves a 30-minute set on the computerized grinding pedestal – sort of a stationary bike for the upper body that simulates the hand-cranked winches on the boat – during which they’re supposed to put out 300 watts of power at 90 r.p.m. for two-minute bursts. McFarlane says the sailors are so strong they frequently rip the handles off the machines. “We’ve gone through so many of them,” he says. “Guys just tear them up.” Craziest of all: The highest setting on the pedestal isn’t even half the load they’re dealing with on the boat.

Elsewhere in the gym, other sailors are on exercise bikes, or doing circuit training with medicine balls and kettlebells.

Spithill, meanwhile, is doing pull-ups with a medieval-looking chain around his waist and two 45-pound plates dangling off of it. “Good, Jimmy!” McFarlane says. “That’s not so hard, right?” Spithill grimace-smiles and does another.

The sailors all agree that Spithill is the fittest guy on the team. “He’s a freak,” Rome Kirby says. “I’d honestly put him up against the top athletes in the world.” Two days earlier, Spithill did a CrossFit challenge, a stand-up-paddle race, and a team sailing regatta, all on a Sunday, his day off. At a recent hydrostatic weigh-in, his body fat was 6 percent. Most impressive of all is that, as the skipper, Spithill doesn’t need to be fit in the slightest: The most demanding thing he does on the boat is spin the steering wheel. But going less than all out just isn’t part of his makeup. “Rarely,” he says, “have I seen a situation where doing less than the other guy is a good strategy.”

Other than Spithill, though, everyone on the boat has a physical role. Take John Kostecki, better known as J.K., a 49-year-old America’s Cup vet who is currently heaving a 15-pound medicine ball several feet into the air. Kostecki is a tactician, the sailor responsible for plotting the boat’s course during a race. It used to be that he could sit at the back and watch everything unfold, keeping an eye on the current, the wind, and the other boats. But on the new boats, he has to grind, too. With a crew of only 11, there’s no room for deadweight. “You can’t carry anyone,” Spithill says.

There are three teams battling it out with Oracle for the America’s Cup this year: Artemis Racing; Emirates Team New Zealand; and Luna Rossa Challenge, from Italy. As the defender, Oracle gets an automatic bid to the finals in September; the other three will face off at the Louis Vuitton Cup in July and August, with the winner earning the right to take on Oracle for the trophy. During the best-of-17 finals, the crew will be sailing two races a day. Slingsby compares it to running a marathon and playing chess at the same time. To prepare, they mix into their workouts some mental acuity tests – silly puzzles and matching games designed to stretch their brains while the blood and oxygen are racing elsewhere. “We need to be able to make decisions when we’re completely exhausted,” Spithill explains. “You make a mistake now and there’s gonna be some big consequences – as we’ve seen.”

At 8:45, it’s time for breakfast. Today’s menu is typically voluminous: scrambled eggs, beans, bacon, grits, toast, granola, cereal, yogurt, fresh blueberries, orange juice, and coffee. Then it’s on to the sail team meeting. The sailors crowd into a small conference room with coach Philippe Presti – a dapper, silver-haired Frenchman who looks like the lead from a Godard movie – who cues up some sail footage from a Go-Pro mounted on the mast. The team dissect each maneuver in their myriad accents: English, French, Australian, Dutch, Italian, American. Although Oracle is officially the American team, America’s Cup crews have long been mercenary affairs. This year, only two sailors – Kirby and Kostecki – are American.

As defending champions, Oracle put together an all-star team. There’s Ben Ainslie, a four-time Olympic gold medalist from England, who was recently knighted by Queen Elizabeth; Shannon Falcone, a bearded Ben Affleck look-alike who grew up on a boat in Antigua and took his first steps on his parents’ 44-foot race yacht; Rome Kirby, whose father is two-time America’s Cup winner Jerry Kirby, and who has been sailing since he was three years old. (Some of his teammates are his dad’s old rivals.) And, in charge of them all, CEO Russell Coutts – with four career Cup wins and a perfect 14-0 match record, the winningest skipper in the history of the America’s Cup.

Coutts and Spithill started putting this team together back in 2010, when the campaign began in earnest. America’s Cup sailors usually get hired for the duration of a campaign, three or four years, during which it’s their full-time job. Contrary to popular perception, none of them are rich, at least not by pro-athlete standards. Typical salaries are in the high five figures or the low sixes, and very few of them come from money. Joey Newton’s dad was a mason in Australia; Spithill’s was a high school teacher. “It’s probably still one of the biggest misconceptions with the game – people think it’s rich old fat guys,” Spithill says. “That may have been true in the past, but we’ve taken pro athletes on the boat, and they’re just blown away.” He was especially gratified when they took surfer Laird Hamilton for a ride. “I can sit and talk forever about how cool this is,” Spithill says. “But when a guy who paddles into the biggest waves in the world for a living goes, ‘That was fucking crazy,’ then shit, it must be crazy!”

The word catamaran comes from the Tamil kattumaram, meaning “tied-together wood.” That is not what these boats are. Technological innovation has been a hallmark of the America’s Cup ever since the very first race, in 1851, when the America, built for the New York Yacht Club by a designer named George Steers, ditched the then standard “cod’s head and mackerel’s tail” design in favor of a longer, thinner hull, and subsequently left 14 boats from Her Majesty’s Royal Navy sputtering in her wake. But this year’s boats are a step beyond.

The AC72 features twin hulls of ultralight carbon fiber, which are coated in polyurethane and Nomex (the same flame-resistant polymer used in nascar uniforms and flight suits) and baked in an oven at 194 degrees, until it’s hard and shiny like obsidian. But the real feat is the carbon-fiber wing sail, which is exactly what it sounds like: a sail that works like a wing. The wing is rigid like an airplane’s and functions according to the same principles of physics. Wind moves across the sail, creating lift – only, because the sail is vertical and not horizontal, it pushes the boat forward instead of up. “These boats are so fast that they basically never sail downwind,” Newton says. “You know how if you stick your head out a car window it still feels like the wind is in front of you? That’s how these boats operate.”

Wing sails made their first appearance in the America’s Cup in 1988, on Dennis Conner’s Stars & Stripes. But since then they’ve become standard, prized for their faster performance as well as their durability. (When Oracle’s boat capsized during the team’s death-defying accident in October, they patched it up with carbon fiber and sailed it for 20 more days.) The newer they are, though, the more futuristic they get: Inside Oracle’s wing, for instance, are embedded fiber-optic cables that collect information about the boat’s performance from some 28,000 data points. “It’s just a mind-boggling amount of data,” says John Kostecki. “It takes 24 hours to process the little bit we want.” Adds Falcone, only half-joking: “It’s a good thing Oracle is our sponsor.”

Oracle, the computer software giant, is owned by Larry Ellison – the fifth-richest person in the world, and the wealthiest in the United States not named Warren Buffett or Bill Gates. He has an estimated net worth of $43 billion and recently bought his own Hawaiian island. Since 2000, he has dedicated a significant portion of his massive resources to winning the America’s Cup. He finally got one in 2010, with a wing-sail trimaran even bigger than the AC72, and a campaign that some analysts say cost as much as $400 million.

“That boat was just a monster,” Newton says of the trimaran, called USA 17. “It felt like the thing was going to collapse around you the whole time.” Just the 200-foot mast cost $10 million – as much as an entire AC72 – and the massive wing sail needed an engine to manipulate it, which scandalized purists. It took two cranes just to get the thing off the dock. “I don’t think we’ll see that anymore,” de Ridder says. “The amount of time and effort that went into that boat was just unreal.”

Ellison, a longtime yachtsman, gave himself an honorary spot in Oracle’s afterguard (the members of the crew responsible for tactics and strategy), and he was onboard when they secured their America’s Cup victory. Coutts, speaking diplomatically, calls his boss “a keen sailor,” and a “competent” one. “He loves the sport, loves the challenge, obviously loves the technology,” Coutts says. “And he’s involved with the big decisions. He might not be in the room, but he gets a full rundown of what’s going on.” According to most of the sailors, Ellison rarely visits the base, and few of them have said more than a couple of words to him. “But he makes it pretty clear,” says Coutts, “that you’ve got to achieve results. Financial targets, performance targets – he expects results.”

This time, having won his Cup, Ellison has even bigger goals. He single-handedly underwrote a new organization called the America’s Cup Event Authority to help sell and promote the event. He also implemented several changes to the race in order to appeal to mainstream sports fans. Ellison, who rarely speaks to the press, declined to comment for this story. But it’s not hard to imagine that – as the self-made computer whiz who crashed the club of financial high society – he now wants to remake the high-end yachting world in his own image as well. “He wasn’t born into money,” Spithill says. “He was adopted, and he worked his ass off.”

For Ellison, the real prize for winning the America’s Cup wasn’t the trophy – it was the ability to write the rules for next time. His longtime dream had been to make the Cup more accessible to the average American, and to that end, he introduced several changes. In the past, the Cup was held far offshore, where seating is hard to come by. Ellison moved it to the picturesque San Francisco Bay, where crowds and TV crews could watch. The Cup was also unpredictable, as less-than-optimal weather conditions like a lack of wind could postpone races hours or even days. Ellison made the boats faster and more maneuverable, so they could sail on schedule and in any conditions. He made the courses shorter and better defined, so spectators could see who was winning. And he helped fund a TV technology called LiveLine – designed by the same guy who invented the yellow first-down line and Fox’s glowing hockey puck – so that even viewers who don’t know a jib from a gennaker could yell at their TVs with authority.But branding efforts and TV contracts aside, even just building and running an AC72 is a massive undertaking. As befits the company’s Silicon Valley roots, Oracle’s base looks a lot like a well-funded start-up, with a staff of roughly 150 (it fluctuates depending on the time of year) spread among more than half a dozen different departments. The shore team, as these nonsailors are called, includes engineers, electronics experts, hydraulics specialists, rigging and sail designers, and boat builders, as well as more traditional operations staff such as lawyers, marketing execs, accountants, janitors, and chefs. A winning campaign typically costs in the neighborhood of $100 million, and more. Given the fact that Oracle doesn’t race until the finals, even if they go all 17 races, the campaign will have cost at least $200,000 per minute of sailing, and possibly as much as twice that.

In the second week of April, Oracle’s new boat is almost finished. Two sailors, Will McCarthy and Brian MacInnes, are painting glue onto a wooden boat mount, which they’ll cover with AstroTurf to keep it from scratching the hull. Meanwhile, MacBeth is up on top of the boat, working on the winches. In addition to sailing, every sailor has his own design specialty and chips in with other jobs around the base. Newton trained as a sailmaker. Gilo Nobilli programmed some of the onboard electronics. Falcone helps design the team’s technical gear. They’re almost like astronauts, in that they have to be both mechanically inclined and down to do grunt work. Imagine Aaron Rodgers refitting the seams on a football, then going out to resod Lambeau Field.

Around 9:30 a.m., it’s time for rollout. Oracle brings the boat inside most nights; at $10 million, it’s not exactly like leaving your Chevy in the driveway. (When they keep it in the water all night, they post guards around the clock.) The process takes three dozen guys about an hour: First the sail is towed onto the dock and lifted by a 200-foot crane, where it hangs feathering in the wind for a few minutes before being lowered onto the boat. Then the crane swivels the boat out over the channel, and drops it in like plopping a toy into a bathtub.

Next a support boat ties up to starboard on the AC72, lashed to its hull like a sidecar, and starts to tow it out into the bay, past a cement plant and some nesting osprey. On the opposite shore, a man with a long-lens digital camera snaps pictures like a paparazzo. This is a “spy” from a competing team – probably Team New Zealand, Oracle’s main rival. Spying is intrinsic to the America’s Cup; not so much Belichick-filming-the-Jets-type espionage, but more akin to baseball scouts checking out each other’s teams at spring training. It’s tolerated, so long as it’s kept within certain limits – when one of Oracle’s spy boats got closer than 200 meters to Luna Rossa last November, they earned themselves a five-day suspension.

In the bay, it’s an absolutely beautiful day. Even the seals are out to play. Two nights earlier, San Francisco had record winds, 70 miles an hour under the Golden Gate Bridge, and it’s still blowing hard: When the AC72 hits the end of the pier and catches the wind, it takes off like a rocket. None of the motorized chase boats can keep up.

On the water, the boat looks amazing – gloss-black and sleek, like an SR-71 Blackbird plane, or KITT from Knight Rider. It flies past an old clipper ship giving rides to tourists, and the two bear so little resemblance that it’s hard to believe they’re in the same family. Sailing etiquette dictates that boats to port are supposed to yield to those to starboard, but the 72 is so much faster and more maneuverable than any other boat on the water that they consider everything else to be standing still. Other sailboats may as well be buoys: Oracle just goes around them.

I’m in a chase boat being driven by a 55-year-old Oracle sailor named Murray Jones, one of the most decorated sailors in the America’s Cup Hall of Fame, one of the few men to win four Cups in a row. (If that’s not impressive enough, consider how good a sailor he must be for the best sailors in the world to call him the Captain.) The AC72 cruises the bay for a while, slicing back and forth between Alcatraz and the Golden Gate. Near the marina, it zooms past a flock of tiny Optimist boats, some grade-school kids taking one of their first sailing lessons, and the kids gape in awe.

John Kostecki, a native of San Rafael, has been sailing in the San Francisco Bay all his life. He says it’s one of the hardest places to sail in the world. “Here in Northern California, we have this steep, clifflike coast, especially underwater,” Kostecki says. “So we get these upwellings where there’s a lot of cold, deep water pushed up, and at the same time, the air in the San Joaquin Valley gets incredibly hot. So that’s a perfect breeding ground for strong thermal sea breezes.” On top of that, he says, the current is tricky, because the runoff from the Sierra Nevada is being forced through the narrow Golden Gate. Combine the two, Joe Newton says, and “it’s just nuclear. You get a dense, strong breeze and the current running out underneath, and it’s a really sketchy place to sail.”

After a while, Oracle is joined on the water by the Swedish team. They line up a few times for some practice runs, racing back and forth to an imaginary point, like a friendly pickup scrimmage. Oracle keeps up on the upwind legs, which is a good sign, because that’s where Artemis is supposed to be faster. On the downwind legs, Oracle destroys them.

The difference between the two is that Oracle’s boat can foil. Hydrofoiling, or foiling for short, is when the boat’s two hulls lift fully out of the water, as the boat skims along with nothing but the two razor-thin daggerboards keeping it from floating away. When the rules were written, none of the teams expected to foil. “In fact,” Coutts says, “the rule was written to prevent it.” But one by one, the teams discovered a loophole that made it possible. Artemis was still working on it.

De Ridder says that when Oracle first started learning to foil in the AC72, “we were lunatics. We were completely unstable.” It’s a trade-off between speed and stability – basically, how unstable you are willing to be in order to go very, very fast. Even now, they’re still trying to master it. As the AC72 slices across our bow, with nothing but a couple millimeters of carbon tethering it to the water, I joke that it looks like it might fall over at any second. At the wheel, the Captain cocks an eyebrow. “That’s because it could,” he says.Jimmy Spithill was born to be on the water. He grew up on Scotland Island, a half-mile speck in Elvina Bay, just north of Sydney. There were no roads or cars, and to get to the mainland for school and grocery shopping, they had to take a boat. Spithill didn’t even own a car until he was 27. “I was never really interested,” he says, sitting at a picnic table next to the water outside the Oracle base. “It was always boats for me.”

Spithill started sailing when he was seven, when some neighbors threw out an old wooden dinghy they’d kept under their house, and he and his dad fixed it up. He entered his first race when he was 10, with a crew consisting of his eight-year-old sister, Katie. He won handily and soon started sailing youth regattas at a nearby yacht club.

Spithill’s road to the Cup started when he met an Australian sailing legend named Syd Fischer – a former rugby player who was kicked out of the sport for being too aggressive – at an awards ceremony in 1996. Spithill was being honored as a finalist for the Youth Yachtsman of the Year, Fischer as Ocean Racer of the Year. “Afterward I went up to him and said, ‘I’d love to have a go at this ocean racing thing,'” Spithill recalls. “And he said, ‘Well, what are you doing this weekend?'” Spithill steered Fischer’s boat, and they won the race. A few years later, before the America’s Cup in Auckland in 2000, Fischer scraped together some money and asked Spithill to cobble together a team.

They were called Young Australia, and none of the sailors were older than 23. Spithill, 19, was the youngest skipper in history. “It was pretty much a dream job for a 19-year-old,” he says. “We were staying in a campus full of university students, and we definitely maximized our leverage.” At one point, Fischer posted a sign on their dormitory door, reminding them that the legal drinking age was 20, the age of consent was 16, and their curfew was 9:30. “There’d be a bit of a rush to hide girls in closets and stuff like that,” Newton says. “It was awesome fun.”

John Kostecki sailed with an American team from San Francisco that year, and he was deeply impressed by the kid from Australia. “Obviously he was incredibly young,” Kostecki says. “But you could see he was a very talented sailor.” Spithill didn’t win many races – the boat almost sank a couple of times, and at one point they had to put out a fire in the head – but the experience earned him a job at the next Cup, in 2003, as the skipper on Microsoft billionaire Paul Allen’s boat. That team came in third.

At the next Cup, in 2007, Spithill was hired to drive for Italian team Luna Rossa. The Italian fans nicknamed him Jesse James, for his gunslinging ways, and Jimmy Pitbull, for his aggressive starts. They also nicknamed him San Giacomo – St. James. The defining moment came in the semifinals, when Luna Rossa was taking on Oracle. Thanks to some masterful jockeying at the starting line, Spithill forced the Oracle team into two penalties, thus taking a big early lead and effectively ending the race before it had begun. (Oracle’s skipper resigned ignominiously a few days later.) Then, in 2010, Spithill became the youngest skipper ever to win the America’s Cup.

According to the crew, Spithill has a few key talents: He’s a natural leader. He’s impossibly calm under pressure. (“I would say he’s the calmest helmsman I’ve ever sailed with, and I’ve sailed with the best,” de Ridder says.) And he’s extremely, extremely competitive. It doesn’t matter the game: a stand-up-paddle race, a push-up contest, a $20-a-shot basketball competition, a card game, bench press. Newton says one of Spithill’s favorite tricks is hustling for ice cream at Ping-Pong: “He’ll let you get, like, 15 ice creams up, then make you go double-or-nothing and just crush you.”

Spithill says his biggest advantage is the thousands of hours he spent on the water as a kid. “We were on the water every single day,” he says. “We went to school by the water. In our downtime, we would windsurf. We were just looking at the water, and I think that adds up.”

Sitting by the channel outside Oracle’s base, I ask if he can read the water now. He takes a few seconds to size it up. “So there’s very little current here,” he says. “It’s basically high tide, but it’s shifting a bit. There’s very little wind by that wall, but you can also see a gust of wind in the middle – it’s puffy. Also, you see this dark patch in the middle? It’s not moving as quick, and that’s probably because it’s being fought off by a right-hand shift.

“In this channel,” Spithill continues, “the tide is pretty straightforward. But out on the bay, it’s always changing. They have these computer models, but they’re never right. And that’s one of the cool things: trying to piece it together and being a step ahead. Thinking about, if something does go wrong, what’s next? Because as soon as something goes wrong on that bay, it’s like an avalanche. It gets big real quick, and it’s very difficult to get back ahead of it.”

On May 9, the day of the Artemis crash, Spithill was proved all too right. The Swedish team was out training in the main bay. The conditions were moderate, not too rough, and they had already made a few uneventful runs. They were just about to line up again, near Treasure Island, when, in the middle of a bear away – the same maneuver that tripped up Oracle in October – something went very wrong. There was a loud crack, and the Artemis boat listed heavily to port. Then the boat nose-dived, and its crew went into the water.

Spithill was nearby, watching from Oracle’s boat. “It just folded onto itself,” he says. “Then it went straight down.” Oracle’s support crew raced over to help – but the water was strewn with wreckage, and in the confusion, Simpson, the English Olympian, had gone missing under a piece of debris. By the time he was found, it was too late. They pulled him out and tried to revive him, but he was already dead.

All sailing was suspended indefinitely while the race organizers launched an inquiry. There was a lot of hand-wringing about safety requirements and preventive measures. Some people questioned whether the race could – or should – even happen. After their own capsize, Oracle had instituted several safety measures designed to protect sailors in case of another accident, like high-visibility gear and a tank of spare air. They had shared their findings with the other teams, but not everyone had taken advantage.

Oracle’s sailors won’t speculate publicly about what went wrong with Artemis’ boat, saying they’re waiting for the official Coast Guard investigation. But they all agree that it was something structural. “You don’t expect the boat to break in half,” de Ridder says. “When we got there, it was in pieces. It was messy.”

Two weeks after Simpson’s death, Spithill is back at Oracle’s base. Several of his teammates are on their way to the airport to attend the memorial service in the U.K. “A couple of our guys were close, but everyone knew him,” he says softly. “He was one of the world’s best.” Before Oracle’s capsize in October, Spithill had talked about how crashes would be good for the sport, like a pileup in nascar – that’s what appealed to fans. But now, he seems to have reconsidered.

The fallout from Simpson’s death soon threatened to derail the whole Cup. The preliminary rounds had been scheduled to start in July, but because of the damage to Artemis’ boat, they had to sit out while they built a new one. A bigger problem, however, was the rules changes. Race director Iain Murray proposed 37 of them, from lowered wind limits to mandatory high-visibility gear. Most were accepted by the teams unanimously, but two changes sparked great controversy, especially one governing an obscure piece of equipment called a rudder elevator. Team New Zealand and Luna Rossa charged that the rudder change was about performance, not safety, and that it gave Oracle an unfair advantage. Both appealed to an impartial jury, and, in the meantime, Luna Rossa refused to sail. For the first week of the Louis Vuitton Cup, New Zealand ran three races unopposed: two against Artemis (still out of commission), and one against Luna Rossa (boycotting). The Cup had officially become a farce.

The jury eventually decided in the appealing teams’ favor, and the teams were directed to return to the old rudders. Luna Rossa – whom Coutts had derided as “a bunch of spoiled rich kids dressed in Prada” – resumed sailing. Artemis, meanwhile, look on track to be back on the water by the third week in July, but their future was also doubtful: Because they had built their boat with the new-style rudders, it remained to be seen whether they would be allowed to race.

It’s extremely unlikely that, after nearly half a billion dollars, the Cup won’t actually go on in some form or another. But either way, the sailors say, they’re already ruined. “There’s never been any sailing like this,” Tom Slingsby says. “It’s a once-in-a-lifetime opportunity. What if someone else wins, and they decide to go back to boats that go eight knots?”

“I’m going to have to change sports,” jokes Shannon Falcone. “I can’t go back to another boat.”

“It’s that thrill factor,” Spithill says. “The adrenaline is unreal.” He admits that his family worries about him, and that there are times when he himself is…not scared, exactly, but definitely anxious. “But afterward,” he says – once you’re back safe and dry on the dock – “you look back and think, ‘Fuck! How good was that?'”

Contributing editor Josh Eells profiled Blake Shelton in the August issue.

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