At age 8, Paul Cayard began sailing on San Francisco Bay and accumulating a case full of trophies when he wasn’t playing basketball. His natural talent, a fierce, competitive spirit, and strong work ethic attracted the attention of the late San Francisco legend, Tom Blackaller, who invited Cayard on board his Star boat as crew. As a skipper, Cayard became known for his skill around the buoys beginning in 505s as a teenager.

Moving on to Stars, his rise to prominence culminated with a Star World Championship in 1988. Prior to that, Blackaller had signed Cayard on his America’s Cup contender, Defender, in 1983 as a jib trimmer. Blackhaller promoted him to tactician and alternate helmsman for the 1987 campaign. Cayard would participate in five America’s Cups, two as helmsman in the finals, picking up another language (Italian) in the process. He’s also a two-time Olympian.

Cayard’s record in big boats is impressive, with six world championships in various classes, and a host of international, grand prix Cup wins. But Cayard the buoys’ racer surprised the sailing world in 1997/1998 when he skippered EF Language in the grueling Whitbread Round the World Race. Even more impressive, he became the first American ever to win it.

He raced round the world again in 2005/2006 (the Volvo RTWR), finishing second after some perilous breakdowns at sea. “Tacks, off watch,” Cayard said of round the world maneuvers after which sopping wet sails and gear had to be moved to the new weather side, “were like waking up, spending 20 minutes in the gym, then going back to sleep.” He smiles at the recollection.

~ Roger Vaughan