Railroad tycoon, champion contract bridge player (a game he invented), yachtsman, author, and licensed pilot, Harold “Mike” Vanderbilt steered three J-Class sloops to America’s Cup wins in the 1930s. Vanderbilt sailed from birth on his father’s yachts, becoming a proficient helmsman and tactician. From 1922 to 1938, he won six King’s Cups and five Astor Cups. At the helm of Enterprise in 1930, Vanderbilt defeated Thomas Lipton’s Shamrock V, four races to nil. In 1934, Britain’s Endeavour, commissioned by aircraft magnate T.O.M. Sopwith, was loaded with innovations, including a quadrilateral jib. In a best of seven series, the faster navy (Endeavour) blue yacht won the first two races against Vanderbilt’s Rainbow. With assists from the British crew that was striking for higher pay, a hastily made quadrilateral jib of his own, and tactician Sherman Hoyt, Vanderbilt took four in a row to win the Cup.  Three years later, Vanderbilt skippered the “super” J-Class Ranger to a 4-0 Cup win over Endeavour II . During that series, Vanderbilt’s wife Gertude called the time at the start, thereby becoming the first woman to race on a Cup defender. A year later, Vanderbilt and two associates began a complete rewrite of the racing rules of sailing. Their new version of the rules was not approved until 1938. Vanderbilt continued to fine tune them with various committees of the International Yacht Racing Union (now ISAF), until they were adopted in 1960.

~ Roger Vaughan