First offered by Chicago Yacht Club in 1915 to encourage competition between the club and eastern yacht clubs. The first club to accept the challenge was Indian Harbor Yacht Club of Greenwich, CT. Addison Hahan skippered the P Class yacht Josephine to victory for IHYC and the cup went to Greenwich. In 1946, at the suggestion of IHYC, the competition was reinstated using Luders L-16’s and continued for eight years. The challenge was re-started in Shields in 2014.