It is a case of two "firsts'' for Dennis Conner: first to lose the cup, first to win it back.
Dennis Conner is also the only four time skipper in America's Cup history, with FREEDOM in 1980, LIBERTY in 1983, and STARS & STRIPES in 1987 and his catamaran called STARS & STRIPES in 1988. He lost the Cup in 1983 with LIBERTY, and regained it on STARS & STRIPES in 1987.
It was during the losing series that Dennis Conner showed the skill and courage that were to become his trademarks. AUSTRALIA II was a faster boat, thanks primarily to a revolutionary keel and hull shape. She was significantly faster than LIBERTY, faster than a challenger had ever been relative to a defender.
To win, Dennis Conner had to be almost perfect, and he was for three of the seven races In the deciding race that he lost, the lead changed many times with LIBERTY ahead much of the way. On the strength of his character alone, Dennis Conner almost succeeded in winning against unbelievable odds. "It was a sad day when we lost the Cup in 1983", Conner said. "We had two choices for the 1987 America's Cup competition. We could stay home and watch it on television or mount a campaign to win it back." It was no surprise that Dennis Conner took the second option. The 1987 America's Cup was no ordinary race. American technology and pride were on the line when Dennis Conner and STARS & STRIPES challenged KOOKABURRA III in Fremantle, Australia. Dennis Conner and his crew sailed close to a perfect series to win in four straight races. "It seems to me that Dennis had a little bit over everyone else in the world just in this last bit of the regatta", lain Murray, skipper of KOOKABURRA III, said after the fourth race.
In the controversial 1988 America's Cup challenge that went all the way to the New York Supreme Court, Dennis Conner defeated Sir Michael Fay's 120' NEW ZEALAND 2-0 on STARS & STRIPES, the first catamaran to ever compete in America's Cup racing. In 1992, Dennis Conner and STARS & STRIPES went head to head with Bill Koch and AMERICA3 in the defender trials. In the best-of-thirteen finals, STARS & STRIPES lost to AMERICA3 4-7.