How many Americans can say they have been on a winning America’s Cup crew and have won an Olympic medal in sailing? Randy Smyth is a member of that elite club. (For the record there are nine). Soon after Dennis Conner on Stars & Stripes defeated the Australians to take the America’s Cup to his home San Diego Yacht Club in 1987, he received an unexpected challenge from New Zealand’s Cup challenge in 1988. Conner defended the Cup with a catamaran and got a huge assist from his wing trimmer, catamaran ace and Olympic silver medalist Randy Smyth. And, for good measure, Smyth won a second silver in 1992 in Barcelona.

His multihull prowess started at a young age. Along with his 9-year-old brother, David, Randy won his first catamaran race at the age of 11. The brothers raced an Aqua Cat 25 miles from Long Beach, California out to Catalina Island. Like most Southern Californian sailors, young Randy had a singlehanded Sabot, but the Aqua Cat was faster, and he says, “I could take friends along.” Later in 1968 he crewed for Rick Taylor in Germany in the first Tornado World Championship. In 1981 and again in 1982, Smyth and his crew Jay Glazer won back to back Worlds. Smyth’s list of achievements includes both inshore racing and long-distance contests. In the 1980s a grueling 1000-mile multihull race was sailed between Daytona Beach, Florida and Virginia Beach, Virginia. Smyth won the contest in a record 75 hours. No one ever sailed the course faster.

His resume includes 55 national, continental and world championship victories in a variety of multihulls. Today he is a highly regarded coach and advisor. Randy Smyth has also had fun with the media. He consulted on two Hollywood films and sailed different catamarans for Kevin Costner in Water World, and Pierce Brosnan in The Thomas Crown Affair. In 2010, he commentated on the America’s Cup for ESPN and in 2016 covered the Rio Olympic Games for NBC.

As an aside, the other eight Americans with both Olympic medals and America’s Cup victories on the resume include George O’Day, Eric Ridder, Dennis Conner, Conn Findlay, John Marshall, Carl Buchan, Buddy Melges and John Kostecki.

~ Gary Jobson