Dennis Conner isn't like other folks. He isn't even like other sailors. People who race sailboats and people who write about people who race sailboats have been trying to figure him out for years. Why did Dennis say this? Why did Dennis do that? What is Dennis up to now? More often than not the answer is a verbal shrug. "That's Dennis," they say.
Conner, the skipper of Stars & Stripes and the most perplexing personality on the America's Cup scene in Australia, is a wily and fierce competitor whose mind is on sailing 100% of his waking hours. His racing companions say they form tag teams so that late at night Conner always has someone to talk to about sailing. While lesser skippers race for the sport of trying to win, Conner races in order to win. He has defined his sport in his own terms, and his opponents have been forced to accept his definition, like it or not. At the same time, Conner's definition means he can neither court the sometimes useful role of the underdog, nor can he expect to be granted its dispensations even when, as in this year's America's Cup competition, he might well deserve them. He is feared and respected by many, admired by some and loved by very few. After three decades at the top in the tight, gossipy little world of sailboat racing, he remains an enigma, of whom a yachting journalist said, "He's done it all. He's the best there is. His only flaw is that he's Dennis. He's his own Achilles' heel."
This week, in the semifinals of the Louis Vuitton Cup, the 3½-month-long series of races to determine the challenger for the America's Cup, Conner has arrived at his moment of truth. He must beat Tom Blackaller and his double-ruddered USA in a best-of-seven series or be eliminated from Cup competition altogether. In Sunday's Race 1 he got off to a stunning start, taking a thriller from Blackaller by just 10 seconds. And on Monday Conner won again, by three minutes and two seconds, leaving Blackaller a formidable catch-up task. (The winner of that all-American series will meet the winner of the New Zealand-French Kiss series in the challenger finals, starting Jan. 13.)
The stakes would be high at this point in an America's Cup "summer" no matter who was involved, but when Conner and Blackaller, longtime California rivals with many old scores to settle, are slugging it out in what Conner likes to call "a game of life," the battle, for the moment, overshadows the war. It is a perverse but genuine tribute to Conner and to his reputation as a competitor to say that his losing would be bigger news than Blackaller's winning.
Until 1983, when Conner and his red-hulled Liberty lost the America's Cup, the urge to explain Dennis sprang from his success, a competitive record un-equaled in his generation of racers. In small one-design boats, medium-sized ocean racing boats and massive 12-meter campaigns he has won everything that matters most to people who devote their lives and their fortunes—or someone else's—to the sport of racing sailboats. He has won the Star class world championship twice, the Southern Ocean Racing Conference circuit four times, and he has helmed two America's Cup winners: Courageous in 1974, when he was picked out of the chorus line, so to speak, to share the wheel with Ted Hood; and Freedom in 1980, when, to his eternal credit, or shame, depending on who's talking, he reinvented America's Cup campaigning.
The $200 million America's Cup exercise in extravagance that is going on in Western Australia right now was set in motion by Conner and his unprecedented two-year, two-boat Freedom and Enterprise campaign leading up to the 1980 Cup. Until then the typical America's Cup program was five months long, cost around $1.5 million and bore a striking resemblance to sport. Conner's businesslike approach changed all that. With exhaustive attention to detail, thousands of man-hours devoted to crew work and sail testing, and the spending of previously inconceivable amounts of money, Conner laid waste to the defender trials that summer. Freedom won 45 of a possible 48 races, while Courageous, sailed by Ted Turner, and Clipper, steered part of the time by Blackaller, had only four wins between them.
Turner, the last of the true 12-meter amateurs, was so disgusted with the turn the game had taken that he quit 12-metering for good. Blackaller, a San Francisco sailmaker who, like Conner, has twice won the Star class worlds but who, unlike Conner, would prefer to be racing Formula One cars, has twice tried to beat Dennis at his own game: in 1983, with Defender, a boat and a program that came nowhere near measuring up to Conner's, and this year with USA, a gamble on a revolutionary design.
Twelve-meter skippers like Conner and Blackaller are the rock stars of sailing. Typically, they are dashing figures in a glamorous sport who look and feel their best at the wheels of their boats, preferably wind-whipped and wave-lashed. Conner, whose weight goes up and down, mostly up, and whose face has a boyish softness that belies 30-odd years of sun and salt, does not fit the mold. He is a star, nonetheless, because in one sort of boat or another he has beaten them all.
An America's Cup syndicate is a small corporation. Its product is a sleek, 65-foot, 55,000-pound racing machine that is as fast and strong as the corporation's resources of time, talent and money can make her. Most 12-meter skippers view the business side of racing as a necessary evil, a tedious means to a possibly glorious end. They attend to the endless details of preparing their boats because they have been doing it since childhood, and they know that preparation wins races. They scrounge for funds because they have to. However, they would gladly sail a dinghy through an icy gale on the North Atlantic with a broken collarbone if it meant they wouldn't have to put on a blazer and show up for a sponsor's cocktail party.
Conner, by contrast, loves it all. "I come from fairly modest beginnings," he says. "To me it's kind of a rush to get to go and meet people like Edsel Ford or Mike Dingman at the Henley Group, to walk in and see them and be on a first-name basis. I never would have had that opportunity if I hadn't been there asking them for help. I find that fun. I called on Donald Trump and asked him for $3 million. I told him we'd name the boat Trump Card. He gave it a lot of thought. The point is, I enjoy that. I'm a businessman. Sailing is my hobby. It's fun to be a small businessman and to go see how the heavies operate, and see what life is like at the top in another game, if you will, the game of making money."