Jack Sutphen began his America's Cup career in 1958 as a sailmaker with Ratsey & Lapthorn on City Island, NY. He was with the Weatherly campaign that year. In 1974, Sutphen was with the Courageous Campaign as was Dennis Conner. Sutphen had made a name for himself racing against East Coast legends Cornelius Shields and Arthur Knapp out of Larchmont Y.C. When Conner brought together his own Freedom Syndicate for the 1980 Cup, he needed someone to skipper his trial horse in a two year campaign and felt Sutphen had great credentials.
Thus began a pattern of many successive campaigns including the great Freedom triumph of 1980, the U.S. defeat in 1983, and the monumental comeback in 1986-87 in Australia. It was out of Hawaii and Fremantle that year that Sutphen sailed daily with the backup crew on the trial horse to Stars & Stripes as Conner worked toward regaining the Cup. Sutphen's crew was labeled "The Mushrooms," because it was kept in the dark and could be pulled out and "canned" at any moment. "There was a great spirit on that boat," Sutphen recalled. "I think we made Dennis and Stars & Stripes better." This support continued through several subsequent campaigns. He has been with nine America's Cup campaigns from 1958 through 2000, seven with Team Dennis Conner.