The 30: Two Weeks

Inside Joke: Judah Friedlander

Jamie Squire/Getty Images Emirates Team New Zealand and Oracle Team USA

The Peacock and the Raven

Larry Ellison's vision of the America's Cup comes to life in San Francisco. But is it too bold for its own good?

It was freakishly warm in San Francisco on a recent Friday afternoon, but the marble halls of the Asian Art Museum provided cool respite. A guided tour group milled around in a first-floor exhibition hall, peering at a small, dark sculpture of two molelike forms midsquirm.

” … and so nobody painted puppies before that,” a curator was saying, “because no one would commission it.” Moving on to the next piece, the curator continued, “This particular sculpture is one of the earliest of puppies in Japan … “

The puppy sculpture in question, along with several other rooms full of sturdy bronze works, ceremonial warrior duds, massive accordion-style screens, and delicately hand-painted hanging scrolls — some of them featuring additional puppies — were all part of a special exhibit called “In the Moment: Japanese Art From the Larry Ellison Collection.”

Ellison, the billionaire CEO of the Oracle Corporation, has harbored a fascination and appreciation for Japan and its art ever since a visit to Kyoto in 1970. Emily Sano, the museum’s former director, retired in 2007 to kick back in Florence; by 2008, she’d been tapped to be the personal manager of Ellison’s burgeoning private collection of Japanese artwork. And now the Asian Art Museum of San Francisco and its visitors were reaping the benefits of this well-heeled relationship.

“Access to the collection until now has been extremely limited,” a sign outside the exhibit read. “Most of the artworks are kept at Ellison’s residence, a Japanese-style home surrounded by a traditional seasonal garden, where only a few visitors have the opportunity to see them.”

It’s no secret why the collection has been made temporarily public. This summer, the show is running concurrently with another of Ellison’s pet passions, one that similarly revolves around beautiful works of art to which only a select few have access — the America’s Cup. A few years earlier, Ellison had stood right around the corner from the museum, on the steps of City Hall, and discussed his vision for bringing the yacht race to San Francisco in 2013.

Imagine if the team that won, say, the Stanley Cup earned along with it the right to completely revise everything about the NHL. A championship owner could tinker with the league’s salary cap or eliminate it. He could shorten the regular season and lengthen the playoffs; he could mandate that goalies play padless; he could require that to be eligible for the postseason a team must triple the size of its rink and equip its players with sticks made of 100 percent solid gold. Too expensive an undertaking? Too bad.

It sounds out there, but it’s essentially how things work for whoever wins the America’s Cup. First awarded in 1851, the America’s Cup is several decades senior to the NHL’s famous chalice, making it the international sporting world’s oldest active trophy. It has been associated with characters ranging from J.P. Morgan to Ted Turner to, these days, Ellison. The annals of legal history are checkered with America’s Cup–related court cases and appeals and decisions, some of them more closely fought than the on-water battles. It’s an arms race and a design contest; it’s an overprivileged soapbox derby of the sea. It is, as I put it in a blog post on the subject last year, a game of asshole. It is whatever you want it to be. Win it, and you get to define it.

Following two failed attempts to challenge for the America’s Cup in 2003 and 2007, Ellison’s entry won the Auld Mug in Valencia, Spain, in 2010. He earned the right to call the shots, and the result has been a nearly wholesale reimagining of the regatta, from the boats being sailed to the spectators watching them.

As he stood at City Hall that day, flanked by then-mayor Gavin Newsom, Ellison described how spectators would be able to watch the races from land — from office buildings, even! No longer would sailing enthusiasts need a good pair of binoculars, a strong stomach, and a friend with a boat to view the races, typically held far offshore and sometimes lasting for as many as six hours. The races Ellison spoke of would be short and sweet and just a few hundred meters from San Francisco’s Marina District shoreline, where fans could sit in stadium-style seating. The shorter races meant there would be more of them, with the winning boat being the first to nine points. (It had previously never been more than five.)

He projected that more than a dozen boats from around the globe would show up for the preceding Louis Vuitton Cup.1 The Bay would sparkle with round-robin sailing all summer long between boats seeking to challenge the defender Oracle boat, concluding with the September showdown. All this would take advantage of a landscape that he called “the most spectacular natural amphitheater for sailing that God created on this Earth.” Of course, ambitious and expensive real estate development plans were involved, as were taxpayer dollars.

The changes piled up. Gone were the photogenically heeling monohulled Newport keelboats of yore, with their rippling sails and their names like Courageous and Heritage and their crews of short-shorted, polo-shirted Corinthian gentlemen. In their place would be nimble behemoths called AC72s, which share more DNA with a commercial jetliner than with your grandmother’s Sunfish and are staffed by grunts in space-age wetsuits. The boats would fly back and forth in comparatively short races, with the first team to reach nine wins getting to drink from the Cup. And all of this would be televised using neat new technology developed by the same guy who brought you the first-down line and the glowing puck (and who is, himself, also a sailor). It would all be a boon for the sport, and for San Francisco.

Two years later, Ellison’s vision is finally playing out live, though it’s maybe not looking quite the way it did in his head. His Oracle Team USA boat has taken three races against the challenger Emirates New Zealand, but the Kiwi boat has won seven and could end the entire regatta today with a pair of first-place finishes.2

While the last few months have been marked by catastrophic crashes and illegal shenanigans and tumbleweeds blowing through near-empty venues, the last few days have featured immensely competitive, thoroughly enjoyable racing in an unprecedented setting. (Sunday’s races in particular had Cup organizers in a chipper mood.) It’s just too bad it’s a setting that the America’s Cup might not be returning to anytime soon.

 Alcatraz Island

The California Promotion Committee was being a little bit opportunistic when it sent a note to the New York Yacht Club singing the praises of San Francisco Harbor. With a wealthy and well-known captain of industry using his deep pockets to indulge his love of sailing, the sport was becoming more high-profile than ever before. And the Bay Area wanted in.

On behalf of California and San Francisco, the committee’s executive officer, Rufus P. Jennings, outlined the benefits of holding an America’s Cup challenge event in the harbor. He cited “the assurance of brisk winds” and included reference figures of their average velocities during the summer months.

“Deep and safe waters on the largest landlocked harbor in the world with 450 square miles of water surface insures a safe and exciting contest which could be viewed from beginning to end by spectators upon the land,” he wrote. “The fact that there is no rain during the summer months is an additional feature.” He made no mention of fog.

“If the competing yachts should be brought through the Suez canal,” Jennings concluded, “the long trip would arouse the greatest interest in this international event.”

It was 1903,3 and the New York Yacht Club–endorsed, 202-foot schooner Reliance would soon be defending the America’s Cup against Shamrock III, owned by popular Scottish tea (and other sundries) magnate Sir Thomas Lipton.

Lipton was in some ways the Buffalo Bills of yachting: Shamrock III was his third of five attempts to wrest the Cup away from the New York Yacht Club. He never did succeed, though his efforts were bully for tea sales. Rufus P. Jennings and the California Promotion Committee didn’t have any luck with the New York Yacht Club, either. The 1903 race was held off the shore of Sandy Hook, New Jersey, as per usual, and Reliance — a “radical-looking boat [whose] designers thought it was a little too radical to be built,” according to the America’s Cup history Sailing on the Edge — easily won. (The dichotomy between the sailing community’s plodding conservatism and its almost futuristic sense of innovation existed even then.)

Four years later, Lipton wrote a letter of his own to the NYYC brass. Arguing that event costs were growing outlandish and prohibitive, he proposed a racing series on smaller and more reasonable crafts. Sailing on the Edge describes their response.

After the NYYC America’s Cup Committee fully discussed Lipton’s suggestion, Commodore Ledyard proposed, and Commodore J.P. Morgan seconded, a resolution declaring that the America’s Cup was “a trophy which stands preeminently for speed and for the utmost skill in designing, construction, managing, and handling the competing vessels, and should, therefore, be sailed for by the fastest and most powerful vessels that can be produced.”4

Oracle Team USA, left, and Emirates Team New Zealand

As it turns out, in the 2013 race, the “fastest and most powerful vessel that can be produced” appears to belong to Emirates New Zealand. Owned in part by the New Zealand government and helmed by 41-year-old Dean Barker, who has been racing sailboats on an international level since he was a kid in an Optimist, the Kiwi boat has had a slight but essential edge over Oracle, particularly in the first few races of the match.

A quick digression: While Ellison’s operation is called “Oracle Team USA” and while we say things like “the Kiwi boat,” there are actually no nationality provisions in the America’s Cup. The “Americans” are helmed by Jimmy Spithill, a 34-year-old Australian, and managed by New Zealander Russell Coutts, 51. Artemis and Luna Rossa, the Swedish- and Italian-owned syndicates that competed in the Louis Vuitton Cup, were each lousy with Brits, Aussies, and Kiwis. And while New Zealanders compose much of the world’s top sailing talent, even the Emirates boat benefited from a pair of influential Americans: boat designers Gino Morrelli and Pete Melvin.

When you stand on Marina Green, which runs along the north shore of San Francisco, you can see Alcatraz, the Golden Gate Bridge, and the hills of Marin County across the bay. In the water there are rental kayakers and there are slow boats to China laden with shipping containers after a stop-over in Oakland. There are picturesque old-timey sailboats beating on, and there are Coast Guard boats meddling, and there are commuter ferries and aqua jalopies. You can see all these things, yes — but if there’s an AC72 on the water, it’s hard to look at anything else.

The America’s Cup has a long and storied history of people being freaked out by the yachts. In the book The Billionaire and the Mechanic, Julian Guthrie writes about America, the Cup’s namesake and a boat built to show off her country’s ingenuity at the 1851 World’s Fair in London:

The Marquis of Anglesey, a member of the Royal Yacht Squadron, formed in 1815 and the first club in England granted the “Royal” designation, took one look at America and said, “If she is right, we are all wrong.” Another Brit remarked that the America looked like a “hawk among pigeons.”5

There was the “radical” Reliance in 1903, and later there would be innovations like the winged keel of the Australia II, which ended the New York Yacht Club’s 132-year grip on the Cup and led to a “legal circus.” (Between all the on-the-water protests and all the hours logged by lawyers, frequent and fervent appeal to the judicial system has long been a part of yachting. In the America’s Cup’s early days, according to Sailing on the Edge, there was a saying: Britannia ruled the waves, America waived the rules.)

And now there are the AC72s. Next to some of their more genteel counterparts, the massive catamarans are vulgar. New Zealand Herald columnist Paul Lewis described them as “slightly wild, almost feral.” Some sniffed that the boats look like tractors. They do appear to have been created from leftover Pacific Rim parts; it’s easy to imagine a postapocalyptic robot tearing the wing from a commercial jetliner and affixing it to a raft. Voilà: Frankenyacht! It takes several dozen men and a huge crane just to dock the things every night.

Oh, and speaking of wings: These boats can fly. Morrelli and Melvin and the rest of Team Emirates were the first to realize that they could get these AC72 sailboats to hydrofoil — basically, to get the great beasts to rise up out of the water like nautical hovercrafts, their hulking bodies supported almost entirely by a thin board shaped a bit like a crowbar. Foiling had “always been part of a fringe part of the sport,” said Adam May, a designer for the Swedish team; indeed, French sailors in particular have long been known for tinkering with foils, and the aptly named “Moth” class of boats skit around like water crawlers. Few had really expected that the 34th America’s Cup would feature hydrofoils, but once one boat did, the others rushed to follow.6

The implications were stunning: With their enormous wing sails and virtually no drag on the surface of the water, the boats could reach speeds that were almost three times faster than the wind powering them. Cars crossing the Golden Gate Bridge are limited to 45 miles per hour. On the water beneath them, terrorcrafts with no engines were hitting 50.

Asking a random San Franciscan about the America’s Cup is like asking a tea partyer about death panels. The former group can be reliably counted upon to mutter something about “a bunch of billionaires with their toys” in the same way that the latter group is sure to unfurl their Don’t Tread on Me flags at the slightest provocation. That, and the name “Larry Ellison” is pronounced with the same crazy-eyed venom as “NOBAMA.”

You can’t really blame them. They were suspicious a few years ago when they kept hearing wild promises being thrown around about revenues and hotel room projections and global melting pots and vague reassurances that taxpayers would be reimbursed by private donors. (According to estimates, the city of San Francisco remains about $4 million in the hole. Also, that article includes the city supervisor calling the race “3 billionaires in a tub.” DRINK!) They were confused by the haphazard marketing around the city this summer, never knowing which races actually constituted the America’s Cup. They either live in the Marina, in which case any hubbub in the neighborhood is a hassle, or they don’t, in which case they probably brag about how they never go there.

They’ve seen one bit of bad news after another, like the fact that only three syndicates ultimately coordinated Cup challenges (as opposed to the “14 teams, 16 teams” Ellison envisioned) because they found the boats too dangerous and/or too costly, or that one of those three syndicates, Artemis Racing, disastrously capsized during a training run in May. It was the second AC72 capsize in seven months — Oracle had flipped in October — but with far graver consequences: Adored 36-year-old crew member and father of two young sons Andrew Simpson was killed.7

In an interview with Charlie Rose, Ellison called Simpson’s death a “freak accident,” but you could tell he was rattled. In 1998 he had been at the helm of his boat Sayonara8 during an annual Sydney-Hobart Race when the boat was trapped in a typhoon; he and his crew survived the storm (and finished first), but six other sailors died. “If I live for another thousand years I’ll never do this race again,” he said at the time, according to The Billionaire and the Mechanic. People in San Francisco have been saying the same thing for months, and it’s looking like they’ll get their wish. And I probably shouldn’t admit this, but I’d be lying if I said I wasn’t a little bit disappointed.

At the Asian Art Museum, the curator was explaining how many of the pieces in Ellison’s collection only very occasionally saw the light of day. In the West, she said, we tend to hang a painting on the wall and leave it there for years on end. In Japan, pieces are rotated in and out of sight. If your boss is coming over, you might prefer to hang scrolls denoting strength or power, perhaps depicting a dragon or a battle scene. If you’re courting a woman, you’d display symbols of love, luck, and prosperity. (I tried to imagine Larry Ellison calling up Emily Sano and being all, “Tonight I’ll be needing the puppies.”)

“We take for granted things that are always there,” the curator said. “People who live in beautiful houses with a view don’t appreciate the view.”

The view, once the America’s Cup races finally began after so many years of buildup, has turned out to be surprisingly fetching. For one thing, Oracle and Emirates are worthy adversaries: While the Emirates boat has been faster throughout the regatta, there’s no question that in the past few days that gap has narrowed and at times even reversed. Many of the races have featured numerous lead changes — something that hadn’t happened too often in the open-sea, hours-long races that the America’s Cup had long been known for. There’s no love lost between Jimmy Spithill and Dean Barker, who have made for a compelling pair of rivals. The televised product is aesthetically pleasing; the boats, seen up close, make you gasp.

And with a first-to-nine format, there have been shifting narratives, crushing mistakes, noticeable tactical improvements — and plenty of time for the overanalysis of each and every tack and jibe. Kiwi yachtsman Brad Butterworth compared Oracle’s boat to “inmates running the asylum” after Race 5, which was so ugly that the team exercised their onetime right to postpone the next one. Later, they demoted tactician John Kostecki, one of two actual Americans on the boat, in favor of British Olympian Sir Ben Ainslie.9

Last Thursday, after Oracle lost its sixth race, Spithill tried a little reverse psychology on Barker. Asked about the pressure he was feeling, he turned the question around. “I think the question is, imagine if these guys lost from here,” he said, almost smiling. “What an upset that would be. They have almost got it in the bag.”

It was classic Spithill — a little cocksure, a little nudging, trying anything to rattle the preternaturally composed Barker. (When Oracle won the next two races — one in which the Emirates boat nearly capsized — you almost began to wonder if something was working.) But two days earlier, still stinging from Oracle’s most discombobulated showing, he’d been slightly more honest and raw. Asked if he felt like his job was secure, he sighed and said: “You can be a rooster one day, and a feather duster the next, mate.”

Spithill’s colorful response reminded me of a pair of the big six-paneled screens on display at the Asian Art Museum. The left one featured a giant peacock in full and glittering plumage; on the right was a raven staring at a lone discarded peacock feather. The placard explained:

The peacock and raven pairing is unusual in Japanese art. The painter of these screens, Usumi Kiho, may have been inspired by a fable attributed to the ancient Greek storyteller Aesop, in which a plain bird (a jay or a crow) picks up a dropped peacock feather and parades with the magnificent plume in his tail. The fable’s moral comes in his friends’ mocking words: “It is not only fine feathers that make fine birds.”

Last summer, Ellison bought an island — specifically, 98 percent of the Hawaiian island of Lanai. The place came fully furnished. According to the Wall Street Journal, for $300 million he acquired “many of the candy-colored plantation-style homes and apartments, one of the two grocery stores, the two Four Seasons hotels and golf courses, the community center and pool, water company, movie theater, half the roads and some 88,000 acres of land.”

The purchase was the latest of his personal acquisitions. In 2009 he bought a tennis tournament, the BNP Paribas Open at Indian Wells, for a cool hundred million,10 then spent another $43 million to buy a nearby compound of houses. That number doesn’t include the cost of buying 35 couches, 70 chairs, and a hundred ottomans from Pottery Barn to furnish the place, as Guthrie reported in The Billionaire and the Mechanic.

She outlined some of his other holdings throughout the book: a Newport mansion, 11 houses in Malibu, a thousand species of orchid, two places in Kyoto, one in San Francisco, art — lots and lots of art — however many sailboats and megayachts, a Bugatti, a McLaren, a race car, and a few shares of a small going concern known as Oracle.

That’s a lot of fine feathers. In this context, what’s another hundred million or so to try to build and race the world’s fastest boat?11 Larry Ellison is the kind of rich that makes you daydream: What would you do if you could do anything? Who would you become if your every strange compulsion and peculiar obsession could be automatically indulged to the point of such excess? What’s tough is that the relationship to perfection is asymptotic — get close enough, and each incremental step won’t move you much closer.

After all the plans and the negotiations and the escalating costs and the R&D and the international espionage and the tragedy and the adrenaline and the municipal squabbling — after all this, your boat’s not even the fastest. It’s part of the silliness of this big bizarre race, but it’s also part of the allure. Most people don’t appreciate the view; Ellison’s problem may be that he’s obsessed with it.

Ellison’s personal curator, Sano, told San Francisco magazine that when she brought him the Peacock and Raven screen for consideration, “Larry’s reaction to this was so interesting.

“In his mind,” Sano said, “the raven is looking back at the peacock and saying, ‘Hah! You’re all dressed up, but you can’t even fly.'”

This article has been updated to correct the name of the 1998 race that took the lives of six sailors.

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Katie Baker is a staff writer at Grantland.

Archive @ katiebakes