While only a schoolboy when the first SHAMROCK came over to challenge in 1899, "Mike" Vanderbilt was destined to rebuff Sir Thomas Lipton's fifth try for the Cup. In 1930, as the skipper of ENTERPRISE, he defeated SHAMROCK V handily in four straight races, marking the end of Lipton's America's Cup challenges.
A great-grandson of "Commodore" Vanderbilt, who founded the New York Central in 1869, Vanderbilt was always more interested in sailing than he was in railroads.
He skippered RAINBOW in 1934 against T.O.M. Sopwith's ENDEAVOUR, one of the closest matches in America's Cup history. ENDEAVOUR won the first two races in the 4 out of 7 series and was ahead in the third race. Expert strategy and superb sail handling by Vanderbilt and his tactician, W. Sherman Hoyt, allowed RAINBOW to recover and win the next three races.
In 1937, Vanderbilt skippered the "super J" RANGER, the last J-boat to defend the America's Cup. As an owner and skipper of large yachts, he won six King's Cups and five Astor Cups between 1922 and 1938. Vanderbilt is also credited with developing the yacht-racing rules that are the basis of those in force today.