Paul Cayard began his sailing career by winning in a tiny El Toro dinghy at the age of eight. Years later, he remarked, “As an eight-year-old, sailing just bit me. I really liked it. As a kid you’re always doing what your parents tell you. But when I was on my boat, I was the captain of my ship. I was in charge of my own destiny.”
One word that defines Cayard’s remarkable career is “versatile.” He has won seven World Championships and the Whitbread Round the World Race, competed in seven America’s Cup campaigns, and is a two-time Olympian. Beyond all this racing experience, he became one of the most effective communicators of the joys and challenges of grand prix yacht racing.
Rounding out those accomplishments are some notable complementary skills. Due to his European family roots, Cayard is fluent in English, French, and Italian; he is a licensed pilot and has demonstrated effectiveness as a marketer and manager. He learned about business practices from many of the titans of industry with whom he raced over the years. In the process, Cayard became a strong leader and a vital asset in running an America’s Cup campaign.
Cayard was first recruited for the Cup by the late Tom Blackaller to serve as a sail trimmer aboard the 12-Meter DEFENDER in 1983. The boat had below-average speed and was eliminated early from the defense trials. Despite this disappointing showing, Cayard was smitten and jumped at the opportunity to try again. His next campaign would be as tactician for Blackaller in the 1987 America’s Cup in Fremantle, Australia. Their innovative boat featured a forward canard rudder, a bulbous keel, and a traditional rudder at the stern. At times, they demonstrated remarkable speed, advancing to the semi-final round. After two America’s Cups serving as crew for Blackaller, Cayard realized it was time to branch out on his own.
In 1988, Cayard won the International Star Class World Championship in Buenos Aires, Argentina. With his Star Class victory, he gained considerable international notoriety. Business mogul Raul Gardini recruited Cayard to skipper his maxi yacht, IL MORO DI VENEZIA. In 1988, they won the Maxi Yacht World Championship. Cayard encouraged Gardini to challenge for the next America's Cup in 1992. For Cayard, it meant joining an Italian team. He spoke Italian and felt right at home with the crew. Gardini and Cayard won the Louis Vuitton Cup Challenger Trials but lost to AMERICA3 in the America’s Cup final, 4-1.
In 1995, he served as helmsman for Dennis Conner’s America’s Cup defense effort. They reached the Cup final again but lost 5-0 to New Zealand. The American boat was outmatched by a faster boat and perhaps a more polished crew. The Royal New Zealand Yacht Squadron scheduled the next match for 2000.
It was a long wait, and Cayard filled the time with a remarkable victory. He was a noted small boat champion and a match racing specialist. Shifting gears, he was recruited to compete in the Whitbread Round the World Race. Although Cayard had done some long-distance racing, he had never faced anything as compelling or exhausting as the Whitbread. Cayard also found another opportunity to maximize his exposure. The Whitbread organizers allowed the sailors to communicate with fans during the long ocean legs, a practice that had never occurred in ocean racing up to that point. Cayard excelled at writing articulate accounts of facing squalls while racing around the Southern Ocean or drifting endlessly while crossing the doldrums near the equator. EF LANGUAGE went on to win the Whitbread, and Cayard was recognized as a small boat sailor who had mastered long-distance racing.
With the momentum and confidence gained from winning the Whitbread, Cayard launched a campaign for the 2000 America’s Cup in New Zealand. This time, Cayard challenged on behalf of his home club, the St. Francis Yacht Club. His team, AmericaOne, reached the Louis Vuitton Cup final against the Prada Challenge from Italy.
In the best-of-nine series for the Louis Vuitton Cup, with the score tied at 4-4, the final race was quite a show for everyone, with the lead changing hands multiple times during the race. Cayard came up short, losing the 18.5-mile, six-leg race by 47 seconds. For many, such a tough defeat might spell the end of the line, but Cayard had greater ambitions.
After all his Grand Prix racing, he took up a new venture as a leader committed to giving back to the sport. Cayard served as board chair of the St. Francis Yacht Club, from 2018 to 2020. In 2024, Cayard was the President of the International Star Class Association. In September of that year, Cayard won three of six races in the Star World Championship sailed off San Diego against 64 boats, and finished in an impressive fourth place. At that time, Cayard was 65 years old.
With a lifetime of experience, Paul Cayard understands what it takes to prevail at the highest levels of sailing. “Sailing, like all sports, is extremely competitive and there are a lot of young, hungry sailors who would love to be sailing in the America’s Cup or the Olympic Games,” he said. “It takes nothing short of total dedication. Boats are much more athletic now. I’ve always considered myself athletic. It was bred in me, not from sailing, but from playing football and basketball in high school, and I’ve always stayed in great shape. Where sailing is right now, if you are young and you want to be at the top of this game, you might as well adopt the 100-meter sprinter’s training regime.” Paul Cayard is the epitome of what a top athlete is all about. It’s a proven formula: keep reaching high, learn from your mistakes, and move on to the next adventure.
