Paul Cayard is one of the very few sailors who has competed at top level in the three disciplines of the sport: The Olympics, The America’s Cup and Offshore round the world racing. It is impossible to shrink his career to a few lines; with over forty years of experience in sailing, he more than earns his title as a legend of the sport. Cayard has won World Championships in seven different classes. He is a seven-time America's Cup competitor and circumnavigated the world twice, becoming the first American to win the Whitbread Round the World Race in 1998 and placing second with the Disney syndicate Pirates of the Caribbean in the 2005-2006 edition of the Volvo Ocean Race. Cayard is a two-time Olympian (1984, 2004), and he won the Louis Vuitton Cup in 1992 with the Italian syndicate Il Moro di Venezia, becoming one the most appreciated skippers in Italy. Cayard's accolades include induction to the US Sailing Hall of Fame (2011), and the Rolex Yachtsman of the Year Award (1998), he also serves on the Board of US Olympic Sailing. Out of all of this he will be quick to declare that his most treasured prize is winning the Star World Championship in 1988 in Buenos Aires, Argentina.