The Southern Ocean

Between Australia and Tasmania

December 1998

Sleek, white, and beautiful, Sayonara sailed toward the Southern Ocean, a stretch of sea that circles Antarctica and is home to the world's most treacherous waves. Larry Ellison, at the wheel of his eighty-two-foot, twenty-five-ton maxi yacht, was doing over twenty knots downwind. Feeling the dense air on his face and watching the humidity press against Sayonara's massive mainsail and spinnaker, Larry marveled, "Even Sayonara isn't supposed to go this fast." His boat began to plane, her bow lifting and the stern skimming the water, an angle the carbon fiber rocket was not designed for and had never done. Something was wrong.

In his red foul-weather gear and gray Sayonara cap, Larry looked at Brad Butterworth, a New Zealander with a gentle smile, thick hair, and a cache of major trophies. "Sayonara doesn't plane," Larry said incredulously. "It's great to go so fast, but this is surreal." They were twelve hours into one of the world's most competitive sailboat races and were sailing so fast they were already ahead of where the race record holder had been in twenty-four hours.

Larry and his team of twenty-two men — a who's who of professional sailors and a smattering of notables, including Lachlan Murdoch, Rupert Murdoch's son — had left Sydney harbor on the afternoon of Saturday, December 26, in the running of the fifty-fourth annual Sydney-to-Hobart race. It was the height of summer in Australia and the sun shone brilliantly on the hundreds of thousands of people who lined the shore to watch the start. Sayonara, with her pristine white spinnaker with the red Japanese sun stamped in the middle — Larry's design — took an early lead in the 628-nautical-mile race due south to the island of Tasmania along the Tasman Sea.

Larry, the fifty-four-year-old cofounder and CEO of Oracle Corporation and a billionaire thirty times over, won the race in 1995 and had driven Sayonara to three consecutive maxi yacht world championships since. He wanted to see just how much better a sailor he had become. It will be an interesting test, he told himself of his second Sydney-to-Hobart. There was a clarity to be found in sports that couldn't be had in business. At Oracle he still wanted to beat the rivals IBM and Microsoft, but business was a marathon without end; there was always another quarter. In sports, the buzzer sounds and time runs out. Quarterback Joe Montana, with fifty-eight seconds left on the clock, throws a high pass to the back of the end zone and Dwight Clark makes a leaping grab with his fingertips, winning the NFC Championship against the Dallas Cowboys. Muhammad Ali endures seven rounds of pummeling by a younger and stronger George Foreman before knocking Foreman out in the eighth round, regaining the Heavyweight Championship of the World title. Michael Jordan nails his buzzer-beating jump shot against the Utah Jazz to win his sixth championship. Game over. Winner declared.

By early Sunday morning, December 27, the second day of the race, Sayonara blazed into the southeast corner of Australia, where the open ocean waves grow bigger and stronger, unimpeded by any mass of land. The wind had built continuously with gusts now approaching forty-five knots (about fifty-two miles per hour) and the sky had grown darker. Before the race the Australian Bureau of Meteorology had issued a gale warning, so sailors knew things could get rough. But Larry and most of the men on board had weathered similar winds in the 1995 race.

Sayonara was getting close to Bass Strait, the waters separating Australia from Tasmania, where the shallow sea bottom kicks up waves like surf and swells hit from all directions. Suddenly, a violent gust of over fifty knots accelerated Sayonara, and Larry angled her farther downwind to ease the pressure on her sails and rigging. But it was too late. The huge nylon spinnaker resembling the Japanese flag was shredded like a cotton sheet. With the wind becoming stronger and less predictable, the call was made to hoist the strongest spinnaker — nicknamed "the mini"— they had on board. "That sail is indestructible," Larry said confidently as Sayonara sliced through the whitecaps.

Stress focused the billionaire daredevil, who did aerobatics for fun, surfed in storms in Hawaii — he once broke his neck and the injury nearly left him a paraplegic — and had taken Oracle back from the brink of bankruptcy more than once. He was the world's fifth-wealthiest person just two decades after facing foreclosure on his own home and having his water and electricity turned off because he couldn't pay the bills. His hobbies, by his own admission, were a constant search for alternative stress. He had the same feeling now aboard Sayonara as when he'd landed his Italian Marchetti jet fighter on the 2,600-foot-long runway of the Bay Area's tiny San Carlos Airport: it concentrated his mind, forcing him into the present; and landing a jet on such a short runway was something his friend Steve Jobs had told him couldn't be done.

Sailing directly south on this Sunday morning, Sayonara was pounded by another massive gust and the impossible happened: the indestructible sail broke. The bronze fitting, with heavy threads almost two feet deep in the carbon fiber, had been extruded out of the spinnaker pole and the mini was swinging through the air like loose laundry. Gripping the wheel, Larry wondered, What kind of force does that?

Sayonara was now entering Bass Strait, ninety-five miles long and twice as wide and rough as the English Channel. Like the Bermuda Triangle, the Bass Strait had a mythical reputation; nicknamed the Black Hole, it was a place where vessels were lost or shipwrecked, where boats were snapped like twigs.

The gale force winds abruptly dropped, and the wind...