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."