The Great Oliver Iselin
Sailing World|Fall 2022
His name may not be well-known to today’s America’s Cup managers, competitors and casual fans, but C. Oliver Iselin’s place in the history of this venerable event is considerable.
GARY JOBSON
The Great Oliver Iselin

Winning the America’s Cup requires excellence in a number of areas, including management, financial resources, a leading design team, a fast boat, a top skipper and a smooth-operating crew. If any one of these vital areas is lacking, an America’s Cup effort is doomed. A successful campaign is managed by someone with cunning and integrity, who is pragmatic and calm during the heat of battle. Over the long history of the Cup, few individuals have excelled in this manner, and among them is Charles Oliver Iselin, who sailed in six winning defenses. Every one of his campaigns had unique and strange quirks that challenged one of the most dynamic managers in America’s Cup history.

Iselin’s final campaign was managing Reliance, the massive Herreshoff masterwork that easily defeated two potential defenders and Sir Thomas Lipton’s third challenge in 1903. Eight years earlier, Iselin had his integrity questioned by Windham Wyndham-Quin, the 4th Earl of Dunraven, who claimed he had cheated by secretly adding ballast to Defender in the middle of the night. Iselin had a good reputation and was outraged by the claims. After an exhaustive inquiry and hearings, Iselin was cleared of any wrongdoing. Following this potentially career-ending debacle, Iselin managed three more winning campaigns. In the process, he secured a legacy of excellence that deserves study and recognition.

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