By the time he was 14, he'd won the North American sailing championship in the El Toro class. "I was always very, very determined to win," says Cayard. "I don't know where I got that from. My dad wasn't an athlete. But I never wanted to give up. To me, that was a sign of weakness.
When he got to college—San Francisco State—he decided to switch from fleet racing to match racing, the head-to-head style used in the America's Cup. The top match racer in San Francisco at the time was Tom Blackhaller, who would die of a heart attack in 1989 at age 49. The 18-year-old Cayard knocked on Blackhaller's North Sails office door in 1977 and asked Blackhaller to teach him to match race. "He told me he'd teach me during his lunch hours," Cayard recalls, "but I had to do all the preparations—get the boats on the water, rig them—and put them away afterward."
Cayard so impressed Blackhaller that Blackhaller asked him to crew for him in some Star class regattas. In 1983 Blackhaller, a flamboyant man who delighted in being a thorn in Dennis Conner's side, invited Cayard to be a sail trimmer on Defender during the America's Cup trials in Newport; Conner's Liberty won there before going on to lose to Australia II. Cayard teamed up with Blackhaller again in 1987 in Fremantle, this time serving as his tactician. But the team from San Francisco was again beaten by Conner, and Cayard earned a reputation as a hotheaded adversary, particularly when things weren't going his boat's way. "I've always been very intense and focused," he says. "When I was younger, it was close to out of control."
In 1988 Cayard, who speaks French and Italian, teamed with Italian industrialist Raul Gardini to win the Maxi-boat world championship, which led to Gardini's entry in the '92 America's Cup. Gardini put Cayard in charge of the challenge by Il Mow de Venezia—a four-year, five-boat campaign that cost more than $50 million. "Raul became something of a father figure to me," Cayard says. "He took me in as if I were his son."
Il Mow had a fine run, staging a stirring comeback after Cayard fell behind New Zealand in the best-of-nine challengers' series, four races to one. Or so it appeared. After losing the fifth race Cayard protested, saying the Kiwis had violated an obscure America's Cup rule in the way they had rigged one of their sails to the bowsprit. An international jury reluctantly agreed with Cayard and, while admitting that the rigging had not affected the outcome of the race, threw out the result and ordered a resail. It was the first time in 141 years that an America's Cup race had been annulled. The distracted Kiwis went into self-destruct mode and lost the next four races to Cayard, who proved again that he knew how to rally a team.
Shortly after Il Mow was beaten by Koch's America³, Gardini's life came down around him. In an anticorruption crackdown, Italian authorities began investigating Gardini and his chemical company, Montedison, for alleged bribery of public officials. Rather than face a criminal trial, Gardini committed suicide in 1993. Cayard had seen him a few days earlier. "I knew he was stressed out, but [his death] was still a shock," Cayard says. "I had a special relationship with him, just as I did with Tom Blackhaller. Now neither of my two greatest sailing influences are here to see what a good job they did. I think about that a lot."
Just as he thinks about how perfect the timing would be if next year he fulfills the dream that Gardini chased, that Blackhaller chased and that Cayard himself has chased since 1983: bringing home the America's Cup. Cayard says he wants to spend more time with his kids—son Danny, 10, and daughter Allie, 9. Between the Whitbread and the end of the forthcoming America's Cup, Cayard will have spent 24 of the past 30 months on the road. Rather, on the sea. "I've been on a five-year tear," he says, "and during that time my kids have gone from being toddlers to young people with their own personalities. I don't want to miss the next five years. So I've got more invested personally and emotionally in this America's Cup than in any of the other four."
It is an investment he clearly does not regret as he stands on the deck of AmericaOne, his 49er. It is new and fast and eye-catching, with many races to win before this sailor can come home from the sea.