NASCAR on water: The billionaire fight for the America’s Cup

In the name of all things that go fast, Neal Pollack went to San Francisco to explore the world of America's Cup yacht racing. - Ed.

All summer, it had been whispered around the piers: “The Kiwis are better.” In the Red Bull Youth America’s Cup, New Zealand’s 45-footers ripped to a one-two finish, beating the world’s top young sailors, many of them seasoned Olympians. The U.S. boats, in particular, were left sucking the Kiwi wake.

Now the real America’s Cup was about to dawn, and the Americans were in trouble. The Cup was theirs to lose. A loss suddenly seemed likely. They’d watched New Zealand destroy a decent Italian crew in the semifinals. The Kiwis were a flawless machine. Their boat was a monster.

For years Larry Ellison had strutted across the sport like a randy rooster tech lord, pasting the sport with his Oracle brand. The 72-foot catamaran that Ellison, as the title holder, had chosen for the America’s Cup, with its giant 130-foot carbon-fiber wing sail and its insane ability to fly both hulls above the water, was the definition of show-offy. San Francisco worships wealth, but disdains conspicous displays. The town likened the boat to a giant phallic symbol running around the Bay. Columnists decided that the America’s Cup was a “bust,” a “fiasco,” a mindless display of power and rich-guy technology. In a town that loves its home teams, no one really wanted Oracle to win.

Schadenfreude swelled the week leading up to the race. Oracle got caught cheating. Earlier in the year, one of their 45-foot training boats had broken apart and washed up ashore. In the wreckage, investigators found that someone had added weight to some forward posts during some preliminary races. In the America’s Cup, all boats have to be built to the exact same specifications. All differences are illegal, and these were big differences. Oracle got fined $250,000, milk money for Ellison. But more importantly, they lost their lead wing-sail trimmer for the entire regatta, and a grinder for four races. Also, they got docked two points, meaning they’d have to win 11 races in the Cup series, as opposed to New Zealand’s nine.

The race day dawned cloudless, more like Southern than Northern California. On the water, the temperature registered 62 degrees, with the wind a pleasant 18 knots. It was a perfect day for sailing.

The guns went off.

New Zealand seized a small lead. Oracle was a little slow getting to the start. But it was close. The boats crossed each other tightly several times, seeking to gain starboard advantage. They whistled into our purview, sleekly skimming over the water. For all the scandal and the wealth-bashing, at the end of the day, sailing had finally happened, and it was lovely to watch.

A cheer went up. Oracle had seized control of the race in the second turn, with skipper Jimmy Spithill engineering a bold crossing maneuver. The Oracle fans -- and there were some, despite it all -- started to feel hopeful. Maybe all the doubters had been wrong.

But then in the next turn, Oracle swung left for current relief. The Kiwis tacked brilliantly, and got the lead back. At that point, they were turning downwind, and it was too late for the Americans. The announcers said, “New Zealand is a little faster, a little lower.” As we watched the denoument on the big screen, a Kiwi fan said to me, “genetically, they’re far superior, and their boat is incredible. Oracle had too many distractions this summer. If you miss one day of learning about technology, you’re lost. It’s a good life lesson.”

New Zealand cruised into the finish 30 seconds ahead. “Oracle needs to spend another $50 million,” someone said to me. Just like that, the home team was down 1-0. Because of the penalty, they needed to win 11 races, so it was effectively 3-0.

There was barely time to breathe before the second race. New Zealand grabbed a two-second lead through turn one, fought off an early Oracle challenge, and then dominated all the way through. The first-day rout was complete, and the Americans were still up against it. If they didn’t come back in day two, the Cup was basically lost.

Earlier in the the summer, I rode on an AC45 with several members of the Oracle team, having gained access to an exhibition race as part of an extreme sports video. My thrilling time on that boat, swaddled in more gear than a Jolie-Pitt baby, showed me one thing: The actual America’s Cup sailors were serious athletes who knew exactly what they were doing. Many of the Oracle sailors themselves came from New Zealand themselves, so it’s not like there was any real difference in sailing ability between the finalists. The New Zealand team just seemed to have a better boat.

Day Two dawned a little chillier and windier on the water than the first day. I watched the races on the Bay, having boodled my way onto a motorized luxury skiff alongside a monied raft of Midwestern yachting fiends, one of whom, a 60-something woman from Ohio, didn’t stop talking the entire time. We learned all about her daughter’s wedding, the time she’d seen Jim Morrison pass out backstage, and the last time she was in Del Mar, when she’d seen “over 36 whales.” We all wanted to pitch her, and her endlessly refilled glass of champagne, overboard, but we resisted.

We were bobbing nearish to Alcatraz when the race started. A few minutes later, the boats came whipping out of the fog, New Zealand foiling and Oracle dragging again. The TV feed said, “The Kiwis don’t make a mistake when they get a lead like this.” Oracle had a brief lead coming out of the first turn, and after that it was all New Zealand. The Kiwis were up 3-0 before the second round of canapes came out of the galley. It was depressing. As Steve McQueen said in The Magnificent Seven, “I never rode shotgun on a hearse before.” The Americans were going down in flames.

The second race followed quickly apace. Our skipper maneuvered us into even better position to watch things. We were right up the gut, so close that our boat got swarmed by speedboats and Coast Guard schooners, honking at us and trying to herd us--and about four dozen private sailboats--off the race course. It was a mess out there in the Bay, and the cargo ships didn’t stop coming either.

The catamarans burst out of the fog like the Romulans chasing the Enterprise. We were maybe 300 yards away, close enough to see Spithill make some sort of minor navigational error, sinking his port-side hull in the water and dragging the rest of the boat down, too, letting the Kiwis pass in the first turn. A collective moan went up on our boat. Toes curled in Topsiders. The U.S was going to lose four in a row. On their home waters. This was an epic embarrassment.

But then Oracle came back. As the boats receded back toward the Golden Gate, we saw that Oracle had retaken the lead and had a very thin 16-second lead. I stood on the bow and prepared for the deluge. Then they appeared, in full THX sound, coming right at us, going at least 20 knots each, charging for the finish line.

Spithill and his crew tacked hard and the Oracle boat spun right in a turn that would have been tough for a motocross boat to take, much less a 72-foot catamaran with a mainsail taller than a redwood. But it moved with a perfect grace and astonishing speed, a hairpin that would have made Senna proud. New Zealand was right behind, and they matched Oracle grind for grind, maybe even gaining a few seconds.

And then, amazingly, the boats both turned again, right on top of the first one, around the fourth gate, at equal speed, a one-hulled move of rocketing desperation. Both boats, yet again, were flawless. But Spithill had his sailors ahead, and they foiled past and through. Oracle had it. Once you’re fully downwind in these races, you’ve won. They charged through the gates eight seconds ahead.

To beat the Kiwis, Oracle had to run a perfect race, and they did. Would they be able to do that ten more times? Almost certainly not. But at least the home team had made a respectable showing. A great cheer went across the water. All around us, the yachts honked their horns. Pip pip cheerio for our boys! It truly had been an epic race.

The America’s Cup is the sport of the rich, a massive waste of money that’s about as relatable to the average person as a weekend at Windsor Castle. But seeing it up close on the water was still incredible. Men have been sailing since the dawn of civilization, and these were the best sailors in the world. To watch them race at their peak was a massive privilege. Still, reality trailed right behind.

“That was a great day,” said our chattering companion from Ohio, “almost as great as my daughter’s wedding.”

Mercifully, we’d be off the water soon.