When Dennis Conner (b. 1942) came out of San Diego YC in the 1970s he was red-hot, and he had a mantra: “If they can do it, I can do it too.” And he did, winning the Star Worlds in 1971 and 1977 and finished second in 1978. He also won the Congressional Cup in 1973 and 1975, and in 1976 he and Conn Findlay won a bronze medal in the Tempest Class. In 1977 he also sailed as tactician and helmsman for the Mariner America’s Cup syndicate, then joined Ted Hood in the _Courageous _ afterguard as a starting helmsman and tactician.
In 1980, Conner successfully defended the Cup with Freedom. In 1983, sailing Liberty, he lost the Cup to a dominant Australia II in seven races, ending the New York Yacht Club’s 132-year winning streak. Not one to take such a loss lightly, Conner came back to the Cup battleground in 1987, going to Perth with _Stars and Stripes _ and taking the Cup back in four straight. In 1988, he successfully defended against the big-boat challenge from New Zealand in what may have been the oddest America’s Cup series ever. New Zealand, the challenger brought a 120-foot mega-sloop and Conner sailed a 60-foot catamaran.
In 1992, Bill Koch beat Conner’s defense candidate, but Conner earned the right to defend again in 1995. Conner, the only man to ever lose the Cup did so again that year, to a strong Team New Zealand.
Conner and Stars & Stripes reunited with the New York YC in 2003, the first time he’s done so since 1983. The campaign was plagued with poor timing and bad luck, losing its second boat to the bottom of the ocean (it was later salvaged and used in Cup competition). Connor’s last challenge ultimately fell short, eliminated from the 2003 Louis Vuitton Cup after the Quarterfinals.