It was years before he got back on the water. He was a wealthy man from the day that Oracle went public in 1985. Surely, when he looked at other people’s boats, he must have thought, “Why don’t I go and get one like that?” “It just never really occurred to me. When I wanted to go on holiday, I’d always go to warm places near the water, like Kona Village in Hawaii, but I never went on boats. I read, rode my bike, surfed a bit, but no boats. As my son, David, got older, he rekindled my interest in a lot of things. He got me back into flying. He got me back into playing guitar. Another David [Thompson] got me back into sailing. Then my ex-girlfriend Kristine convinced me to buy my first motor yacht. It was the summer of 1996, and we were in Sardinia for the maxi sailing world championships. Kristine was standing at the dock and staring at this huge, white 200-foot luxury motor yacht. Suddenly she pointed at Sayonara and said, ‘That’s not a yacht.’ She then pointed at the 200-footer and said, ‘That’s a yacht.’ To my credit, I immediately recognized that she was right, so I went right out and bought October Rose [renamed Sakura by Ellison and subsequently the center of a legal dispute with the yacht broker], a 192-footer, from Kirk Kerkorian for around $10 million. I’d never even been on a big motor yacht until I bought one.”
What Ellison seemed to be saying was that it had taken him a while to realize he was rich enough to indulge whatever desire he might have. “It’s true,” he says. “My life had been focused on work, work, and more work. Oracle had crashed in 1991, and I couldn’t rest until it was healthy again. I didn’t have any time to spend money or think about spending money. I bought a house [in Atherton] in 1992, but that was my only house, and I only had one car. The car was a Mazda RX7. Don Lucas told me I had to get rid of the RX7 and buy a more appropriate car for business. I loved my old rotary-engine RX7, but Don was right, so I sold the RX7 and bought a big silver Mercedes. A few years back Mike Seashols [Oracle’s then head of sales] had looked at my cheap Seiko watch and said, ‘Come on, Larry, you shouldn’t wear a watch like that. You should have a Rolex.’ He then handed me his solid gold Rolex President so I could feel how heavy it was. I went out a bought a Rolex, but in stainless. I just couldn’t deal with the gold. Anyway, it took a while and a lot of help from my friends, but I’m now world class at buying things. I moved from Rolex to Patek Philippe. I still have a Mercedes, a couple of them actually, plus the new BMW Z8, a McLaren F1, and a Bentley. It took me a while to learn how to spend money, but once I got started”—Ellison laughs—“I discovered that I have a real talent for it.”5
So when David Thompson put the idea into Ellison’s head that he might like to get himself a maxi yacht, he was pushing on an open door. But why did he want a pure racing machine instead of just a really nice, big sailing boat? “I talked with Rupert Murdoch about the big luxury sailing yacht that he and his family enjoy spending time on. But I never thought of sailing as a form of relaxation. To me, sailing is about adventure and competition. Sailing is completely unpredictable. If Mother Nature decides to make things difficult for you, it can get pretty intense, pretty fast. You always have to be prepared for that. If I want to relax, I’ll read a book.” I’d mentioned to Ellison a few days earlier a theory I had that people who had very intense work lives often found relaxing difficult and that the best they could do was to find some alternative stress that so fully engaged their attention that it drove everything else out of their mind. Ellison said, “That’s certainly true for me. I’d never heard the expression ‘alternative stress’ until you said it, but it immediately struck me as a perfect explanation for all my hobbies. Sailing and flying are definitely alternative stress activities. Driving the boat or the plane demands total concentration. Playing classical guitar is not stressful, exactly, unless I do it in public, but it requires one hundred percent of my attention.”
So the idea of racing at the very highest level just seemed like an obvious thing to do if you were going to do it at all? “Why not? I could afford a big maxi boat—they’re slightly larger than the America’s Cup boats and maybe slightly faster—and the idea of racing one seemed very exciting to me. My nephew, Judge Jimmy, wanted me to buy a basketball team. But if I bought an NBA team, league rules would prevent me from playing point guard—that plus a strong aversion to public humiliation. Anyway, the point is, I don’t want to watch; I want to play. I want to be a part of the team. I want to be taught by, coached by, and sail with the best people in the business. I like feeling a part of the team at Oracle. I enjoy the people I work with very, very much; otherwise I couldn’t spend so much of my time with them. Sailing is similar in one way, because I love working with the Sayonara crew, but it’s totally different in another, because I’m not the star. I’m just a pretty good amateur driver. The rest of the Sayonara crew are the best professional sailors on the planet. Chris Dickson, Brad Butterworth—these guys are unbelievably good at what they do. They’re the best. When we won our four maxi world championships, I usually raced against other amateur drivers, but some of the time I got a chance to drive against the best professional drivers in the world. I’ve even been at the wheel of Sayonara when Russell Coutts was driving Morning Glory. Imagine going head-to-head with Russell Coutts! How cool is that?”6
From 1996, Sayonara competed in all the maxi-yacht series and nearly all the major ocean races. Ellison says that he missed only one, when his daughter, Megan, was graduating from grammar school. Sailing for several weeks every year, he also thinks his driving skills became better than respectable: “I’m very focused. I put the time in, and my driving got better and better. I did most of the driving during all four of our maxi world championships. Sayonara won every buoy regatta she ever entered. The second-best maxi team, Morning Glory [owned by SAP CEO Hasso Plattner and skippered by Russell Coutts], never beat us, not even in one race. We came second in a couple of ocean races, like Bermuda, but we won every buoy regatta. I’m very proud of that. One of the reasons I did the 1998 Hobart was to find out how much I had improved as a driver since 1995, the first time I did the Hobart. I thought I had improved a lot. I wanted to test myself.” The time Ellison spent sailing—the alternative stress—coincided with accusations from within the company that his new interest and his new toys were taking him away from Oracle.
Naturally, he doesn’t agree. “Winning is a habit. So is losing. Competing and winning at sailing has made me more confident, intense, and determined to win at Oracle. Winning breeds winning. The more you win, the more you want to win. The more you win, the more you think you can win. Three of our four world championships were very close. I won a key start against Morning Glory; I drove past Boomerang during the first windward beat after she got out ahead of us at the start; and I made the critical tactical call on the Bermuda race. Had I screwed those three things up, we would have won only one world championship. But I didn’t screw up, and we won four. I did my job, and so did everyone else on the crew. So we ended up winning them all—even one that seemed utterly hopeless.
“One year, the final race of the maxi world championships was the ocean race to Bermuda. We were comfortably in first place after the buoy racing finished, but we still had to finish at least fourth in the Bermuda race to take the championship. Now, ocean races are rarely included in world championship regattas because they are much more subject to chance than racing around the buoys. You can have the fastest boat and the best crew and still lose an ocean race. In an ocean race the boats are often tens of miles apart, some in much more favorable wind than others. Well, the wind gods really had it in for Brad [Butterworth] on this race. The first two nights, the moment Brad came on watch the wind just died. [During ocean races Sayonara races with twenty-four people, who are divided into three groups of eight. Two of the groups are on watch up on deck while the third group sleeps below.] We were becalmed for two nights in a row. We just went nowhere for hours and hours. After the second day’s position report, we knew we were in tenth place, behind some boats we had never even heard of. Desperate times call for desperate me
asures. I looked at the latest weather charts on the computer and decided our best chance would be to head as far to the left side of the racecourse as possible, where we might pick up more breeze and a better wind angle. This was a very risky bet. Conventional wisdom says that on a long race you stay near the middle of the racecourse and keep your tactical options open. Anyway, I overruled the tactical team and sent the boat to the far left-hand side of the racecourse. We were so far behind I thought that the only chance we had was sailing in a part of the ocean where there were no other race boats. If we got lucky, we’d get a favorable breeze all to ourselves. That’s exactly what happened. The further left we sailed, the more breeze we got. Then we got a favorable shift in the wind direction. Everything came good. We rocketed on by all the boats that were in front of us except Alexia. It was a high-risk call, and I got lucky, okay, I know that. It was a lucky call. But it was my call at a critical time, and it gave us the championship. I’ll never forget it.
“Another thing I’ll never forget is the start of one of the buoy races during the world championships in Newport, Rhode Island. It was just before the gun, and Morning Glory was well set up near the starboard end of the starting line. I had Sayonara to the right of Morning Glory, and it looked like there was no room between them and the buoy. We were both on starboard tack, and Morning Glory had right-of-way because she was the leeward boat. If I couldn’t squeeze between Morning Glory and that right-hand buoy, I was going to have a very bad start. So we eased the sails a bit and headed directly for Morning Glory at about twelve knots. As we closed to about half a boat length of Morning Glory, the guys on Sayonara started screaming, ‘No room, no room, turn the boat.’ Anyway, at the last second I turned up hard. I was going to get a penalty if I touched either Morning Glory or the buoy. But I made it. We started two feet to the right of Morning Glory and two feet to the left of the buoy. It was very close to a massive high-speed collison. We had lots of speed at the start, so we quickly got over the top of Morning Glory, and Chris had me tack onto port and head out to protect the favored right-hand side of the course. I said, ‘Chris, Chris, did you hear those guys screaming, “Turn the boat, no room, turn the boat”?’ He stares intensely right at me with those blue laser eyes and asks, ‘Did you hear me screaming?’ I said, ‘No.’ Then Chris smiles slightly and says, ‘Nice start.’ I think, ‘Wow; Chris never smiles.’ It was my best start ever.”
• • •
Ellison knew that the 1998 Sydney-to-Hobart race was likely to be tough. The wave conditions in the Bass Strait usually guarantee that. “The Southern Ocean, the ocean that circles Antarctica, is unique because there’s no landmass interrupting a wave’s journey around the world. The waves just continuously travel around and around, getting bigger and bigger. The world’s biggest waves, sometimes more than a hundred feet high, form in the Southern Ocean. The shallowest part of the Southern Ocean is a ninety-five-mile stretch of water between southeastern Australia and the island of Tasmania. It’s called Bass Strait. When big waves pass over a shallow sea floor, they become very steep. The friction of the sea floor slows the bottom of the wave and causes the face of the wave to become a vertical wall of water [he makes a gesture with his hands]. Under severe conditions the waves can break. The shallows trip the wave and topple it over forward, just like a wave approaching a beach. In Bass Strait the waves always have steep vertical faces, and they come very close together. They hit your boat in rapid succession—bang, bang, bang—very unpleasant. But they almost never break. In an ocean storm it’s not the speed of the winds or the height of the waves that threatens your survival, it’s the steepness and the frequency of the waves. The constant battering of steep, high-frequency waves can break critical gear and cause crew injuries. A single breaking wave can cause severe structural damage and send a boat to the bottom in a couple of minutes.”
Ellison had wanted to do the race again because he thought he was now good enough to be the primary driver and it was a way of proving himself both as a sailor and as a man. Compared to the big-wave body surfing in Hawaii a couple of years earlier, where he had broken his neck and nearly been left a paraplegic, sailing the Hobart seemed perfectly sensible—macho, but not potentially deadly. It made you more impressive in the eyes of others and gave you a collection of exhilarating memories. He says, “The Sydney-to-Hobart is one of those events that everyone thinks of as cool because it’s dangerous. But it’s not really a dangerous race, I mean, it’s not life-threatening, it’s just a hard, demanding race. You have to be reasonably fit to cope with the pounding in Bass Strait, but it’s pretty unlikely that you’ll get hurt. In 1995, we hit winds of about forty-five knots, got banged around a bit, and won the race. It was just your typical Sydney-to-Hobart. The 1998 Sydney-to-Hobart was not typical. I don’t know how, but somehow I managed to pick the one year out of a hundred when the risk wasn’t an illusion. We sailed into a hurricane.
“During the morning weather briefing, we were warned that there was going to be a storm—forty-plus knots—in the Bass Strait. What a surprise. Predicting a storm in the Sydney-to-Hobart is like predicting a cool summer night in San Francisco. Summer nights are always cool in San Francisco. So wear a sweater. No one was concerned about the storm forecast. No boats pulled out of the race. The weather in Sydney was absolutely perfect. It was warm and sunny, and nearly a hundred and fifty boats were tacking and jibing around the most beautiful harbor in the world, trying to get into a good position for the start of the race. During our prerace maneuvering we managed to break a carbon fiber gear in one of our brand-new winches. Dickson got really pissed off: ‘How the hell can we break one of our main winches in light air before the goddamned race has even started?’ It was a good question. We only had about ten knots of breeze, and you’re not supposed to break stuff in light air. I was driving the boat, and I was glad he didn’t blame me for the damage. Anyway, we didn’t have time to fix the winch before the start of the race, so I had to tack the boat very slowly and very carefully. That made starting more difficult.
“Chris was standing right behind me, barking out tactical instructions. I was at the wheel, doing what I was told. Chris had me stay away from Nokia, the biggest boat in the fleet, because they had a nasty habit of banging into nearby boats. We were looking for a safe start. We got Sayonara into a good position for the beginning of the race, the gun went off, and we got up to speed. We did our tacks slowly and precisely. It was a good start. We rounded the first mark ahead of the rest of the fleet. Sayonara was the first boat to sail out of the harbor, through Sydney Heads, and turn to the south. Hobart is due south of Sydney; you set a course of exactly 180 degrees. As we made our right turn to the south, we dropped the jib and set the spinnaker. The breeze was out of the northeast and increasing. We were going through the water at about fifteen or sixteen knots. It was just about as perfect as sailing conditions could get. We had no idea what was going to happen to us over the next three days. If we had, we would have turned left and gone up north to the Great Barrier Reef. That’s where all the sensible people having sensible Christmas holidays go. Instead we turned right and raced down the Australian coast toward the island of Tasmania.
“The wind was very puffy and heavy with moisture. These big puffs would hit the chute [spinnaker], and the boat would suddenly lift up and accelerate through the water. We were absolutely flying down the coast. It was very exciting. Then this really big puff hits the chute, and it just explodes—gone—ripped to pieces. We had a nice lead on Brindabella, the number two boat, but they caught up to us before we were able to set another spinnaker, a smaller one this time. I blamed myself for blowing the chute. If at the beginning of the puff I had come down fast enough—turned the boat five or ten degrees to the right—maybe I could have saved the chute. I had been driving the boat for a couple of hours, and maybe I was getting tired. I thought I must have been sailing the boat at too high an angle. That’s what put too much pressure on the spinnaker. Maybe I should get off the wheel. So I asked Br
ad [Butterworth] if he wants to drive. The wind is getting stronger, and it’s very puffy, very heavy. It feels different from anything I’d ever experienced. We’re now doing eighteen or nineteen knots, and I’m looking back, checking our lead on Brindabella. Then bang, we blew a second chute. The wind was twenty-five, gusting thirty. And the wind was continuing to build. After blowing two chutes we decided to be safe and set the mini—our smallest, strongest spinnaker. The mini is an unbreakable sail. The mast will rip off the boat before the mini blows up. Brad and I were taking turns driving, and the wind just kept on building. Sayonara was surfing through the water at amazing speeds: twenty-two knots, twenty-four knots, twenty-six knots. It was amazing. Maxi racing sailboats don’t go twenty-six knots. But we were going twenty-six knots. Twelve hours into the race, Sayonara had gone twice as far—twice as fast—as the Sydney-to-Hobart race record holder. Wow, that’s incredible. But what the hell is happening here? Why the fuck are we going twenty-six knots?
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