The very first race took place after Captain John Illingworth, a British naval officer who was stationed in Sydney during World War II, was invited to join a pleasure cruise from Sydney to Hobart, Australia’s second-oldest city and at one time an important maritime center. Only if it’s a race, he is said to have responded. It was agreed, and Illingworth’s thirty-nine-foot sloop Rani beat eight other yachts to win the first Hobart in six and a half days. Until the 1960s it usually took four or five days to complete the course. In the following decades, the average time required shrank to three or four. Plattner’s Morning Glory took just over two and a half days in 1996. The quickening pace reflected two of the biggest changes in competitive sailing: first, the move away from wooden boats, which were constructed according to instinct and tradition, to ones designed with the help of computers and built from fiberglass, aluminum, and space-age composite materials, and second, the transformation of what had been a purely amateur sport to one with an expanding number of full-time professionals.
For most of its history, sailing had proudly resisted the move to professionalism that had transformed many sports. But even Sir Thomas Lipton—whose five spirited but unsuccessful America’s Cup campaigns, which stretched from 1899 through 1930, earned him an almost saintlike reputation—understood the value of sponsorship. The publicity engendered by his prolonged pursuit of the Cup did much to make his tea a popular brand in the United States.
Since then, the level of competition has steadily risen, requiring increasing amounts of time and money. In 1977, Ted Turner spent six months and $1.7 million preparing his winning America’s Cup campaign. The only compensation he gave his crew was room and board. In 2000, five American contenders for the Cup planned to spend the better part of three years and more than $120 million preparing for the contest. Patrizio Bertelli, the head of the Italian fashion house Prada, provided the syndicate representing his country with a $50 million budget.
Ellison, who planned to compete for the America’s Cup in 2003, expected to spend at least $80 million. He would pay many members of his crew upwards of $200,000 a year for the more than two years they would train together. Ellison, who intended to sail on the boat—at least some of the time as its helmsman—would also take advantage of computer-based performance analyses and boatbuilding technologies that had been unthinkable even a few years earlier.
Turner, who had sailed on Sayonara for several races, was of two minds about what has happened to the sport he once dominated. During one race, he told Gary Jobson, his longtime tactician, “There are so many computers. Whatever happened to sailing by feel?”
As one of the computer industry’s pioneers, Ellison had no such qualms.
Ellison, who won the Hobart in 1995, had two goals for the 1998 race. First and foremost, he wanted to take the record away from Plattner. After Bill Gates, Plattner was Ellison’s most important competitor in the software business, and sailing had intensified their rivalry and added a deeply personal dimension. “It’s a blood duel,” Ellison would say, without the slightest suggestion that he was anything but deadly serious. He boasted that his yacht Sayonara, which didn’t race in the Hobart the year the record was set, had never lost to Plattner’s Morning Glory. Ellison and Plattner were not on speaking terms, but they had found other ways to express themselves. During one regatta, Plattner—incensed by what he felt was unsportsmanlike behavior by Ellison—dropped his pants and “mooned” Sayonara’s crew. Ellison’s other goal was to beat George Snow.
Snow, a charismatic Australian who had won the Hobart in 1997, and Ellison could hardly have been more different from each other. The crew on Snow’s yacht, Brindabella, was almost all amateur. On Sayonara, with the exception of two guests—one of them Lachlan Murdoch, Rupert’s eldest son and heir apparent—everyone was a professional. Ten of Ellison’s twenty-three crewmen were members of Team New Zealand, which had won the America’s Cup in 1995 and planned to defend it in 2000.
Ellison had always been upsetting traditions and bucking the odds. After his mother decided she couldn’t take care of him, he was adopted by an aunt and uncle. Ellison never got along with his adoptive father, Louis Ellison, a Russian immigrant who took his name from Ellis Island and worked as an auditor. Growing up in a small apartment on the South Side of Chicago, Ellison wasn’t interested in school or organized sports or anyone telling him what to do. “I always had problems with authority,” Ellison would explain. “My father thought that if someone was in a position of authority that he knew more than you did. I never thought that. I thought if someone couldn’t explain himself, I shouldn’t blindly do what I was told.”
After dropping out of the University of Illinois at Urbana-Champaign and then the University of Chicago, where he learned to write computer software, Ellison drove a beat-up car to California. Although he had little trouble getting hired, staying so was a different story. He stumbled through a raft of computer-related jobs until he heard about a new kind of software that could store and quickly manipulate large databases. Seeing its potential, he launched a business in 1977 that would become Oracle. The company doesn’t produce the kind of software that consumers buy or even know much about, but every organization that stores significant amounts of data needs it. For most of its first decade, sales doubled every year, so quickly that Oracle appeared to be on the verge of going totally out of control. Ellison’s personal life was equally rocky. He married and divorced three times, and he broke his neck in a surfing accident.
In 1990, Ellison was almost booted out of his own company after Oracle disclosed that some of its employees had booked millions of dollars of sales that hadn’t actually materialized. But by the mid-1990s it seemed that Ellison’s high-stakes, step-skipping management style was entirely appropriate for an industry that was changing faster than any traditional organization could. Ellison was confident that no company was better suited than his to capitalize on the burgeoning Internet. After all, the first generation of e-commerce blue bloods—Amazon.com, eBay, and Yahoo!—all relied on Oracle software. Thanks to them, and their gravity-defying stock prices, Ellison believed that the value of Oracle’s shares would also explode. And he thought that would enable him to achieve his ultimate ambition—to replace Bill Gates as the world’s richest man.
Ellison had always been interested in sailing. As a child, he imagined being able to travel to exotic places on the yachts he saw on Lake Michigan. Soon after he moved to California, he bought a thirty-four-foot sloop, although he gave it up because he couldn’t afford it. In 1994, Ellison’s next-door neighbor, a transplanted New Zealander named David Thomson, suggested the idea of building a maxi-yacht. The largest kind of boat permitted in many races, maxis are about eighty feet long. Ellison said yes, but he imposed a couple of conditions. First, he wanted it to be the fastest boat of its kind. Second, he wanted Thomson to do all the work. Thomson was a private investor affluent enough to live in Ellison’s neighborhood, but he wasn’t in a position to spend 3 or 4 million dollars for his own maxi. Deciding that it would be fun to oversee the design and construction of Ellison’s boat, Thomson readily agreed to his terms.
Typically, when someone decides to build a boat, he or she wants to be involved in the plans, but Ellison made it clear that he didn’t want to know about the details. When Thomson walked over to Ellison’s house with a set of engineering drawings, they spent only a few minutes talking about the boat before Ellison turned the conversation to his newest plane, which they discussed for more than an hour. Thomson did send Ellison occasional e-mail updates. At the end of one, Thomson, who had heard that Ellison was going to the White House for a state dinner honoring the emperor of Japan, asked about the protocol for such an occasion. “What will you wear? Do Americans bow to the emperor?” At the end of the e-mail, Thomson wrote, “Have a great time. Sayonara.”
Seconds after he pushed the SEND button, he sent another e-mail: “Sayonara. That’s not a bad name for a boat.”