Dennis Conner

Conner has won the America's Cup three times, successfully defending the Cup in 1980, and 1988 and winning as the challenger in 1987. His 4-3 loss in 1983 to Australian Alan Bond's controversial wing-keeled challenger Australia II was the first Cup defender to be defeated in the 132-year history of the race, simultaneously ending a run by the New York Yacht Club that began with the first contest. Following the loss Conner formed his own syndicate, the Sail America Foundation, through which he raised funds to mount a challenge on behalf of the San Diego Yacht Club, culminating with winning the Cup back from Australia in 1987.

Representing the San Diego Yacht Club (SDYC), Conner's Sail America Foundation faced another controversial challenger in "1988", backed by New Zealand banker Michael Fay.[3] Fay's team abandoned the 12-meter format that had prevailed since the pre-WW II demise of the massive and fantastically expensive J-sloops, and challenged with a huge and unconventional 90' super-sloop (KZ1). Conner responded with an even more controversial 60’ wing-sailed catamaran (US-1) in a surprise defense.

Fay's challenge and legal case based on the Deed foreshadowed the controversial 33rd America's Cup, whose legal wrangling resulted in the contest being decided in enormous multihulls in February 2010,[4] while returning to the pre-war style of exclusive, billionaire backed campaigns of Alinghi and BMW Oracle Racing.

Before the 1980s, America's Cup competitors were mostly amateurs who took time off to compete. Conner insisted on year round training with a new focus on physical fitness and practice. This change in approach led to a return to professional crews in sailing, which had hardly been seen since the 1930s.

A photo of America's Cup winner Dennis Conner while aboard a replica of the original Cup winner "America" in San Diego in 2010

Perhaps due to the bad media attention surrounding the 1988 catamaran defense, Conner had insufficient funding to mount a multiple-boat defense in 1992, which also heralded the debut of the IACC yacht. His USA-11 proved no match to Bill Koch's America3 campaign. USA-11 was built as a test-bed for design ideas that were to be incorporated into the "racing" boat, nicknamed TDC-2. However, TDC-2 was never built. Its ideas were incorporated into his single-boat campaign for 1995, and the yacht Stars & Stripes USA-34. After almost sinking during The Citizen Cup defender trials, USA-34 went on to a come-from-behind win over Mighty Mary, earning the right to defend The Cup against Team New Zealand's Black Magic, NZL-32. Believing Stars & Stripes was no match against the Black Magic, Dennis Conner swapped boats for the Cup matches, pitting Young America against New Zealand's Black Magic NZL–32. But the result was a humiliating defeat for Dennis Conner, losing to Team New Zealand 0–5.

Conner again found difficulty securing funding for the 2000 America's Cup in Auckland, New Zealand. As in 1992 and 1995, he mounted a single-boat campaign centered upon Stars & Stripes USA-55. Conner was eliminated in the quarter final repechage by Craig McCaw's OneWorld Challenge.

Conner was a rare non-billionaire fielding a team to compete in the 2003 America's Cup, held in New Zealand, receiving funding of up to US$40 million from his sponsors. His syndicate, Stars & Stripes, suffered a severe setback before they departed California, as one of the two Stars & Stripes boats (USA-77) sank when its rudder post failed during training. Despite raising the boat from 55 feet of water and eventually repairing it, they were unable to recover the valuable testing time lost and they were defeated in the quarter-finals of the Louis Vuitton Cup.

2003 marked Conner's last participation in the America's Cup.