C. Oliver Iselin's sailing career began with small, over rigged boats known as sandbaggers. These were wide, shoal boats on which capsize was always imminent. He raced catboats in Long Island Sound and gained a reputation as a keen racing skipper while still in his teens.
Iselin, whose grandfather had amassed a large fortune in the importing business, was elected to the New York Yacht Club in 1877. Within ten years he found himself a crew member aboard VOLUNTEER in 1887. This experience no doubt led Iselin to successfully manage the Cup yachts built by Herreshoff. He headed up the VIGILANT syndicate in 1893, the same year the Earl of Dunraven was elected to the New York Yacht Club as an honorary member.
Aboard DEFENDER in the 1895 Cup challenge, Iselin was at the center of the Earl of Dunraven controversy. As his honor and that of his nation were in question, Iselin put his fate in the hands of a New York Yacht Club committee which vindicated him and gaulted Dunraven. Being the great sportsman and yachtsman that Iselin was, he offered to resail the entire match. Few could equal his experience at racing and tuning these great yachts and few could equal his sense of dignity and honor in the face of poor sportsmanship.
In 1899, Iselin managed the syndicate that built the Herreshoff yacht COLUMBIA at an astonishing cost of $250,000. Coming out of retirement to manage the RELIANCE in 1903, Iselin oversaw a perfect defense that year. As manager of these Cup Defender syndicates, he showed the embodiment of America's Cup spirit. He understood the great yachts, commanded with authority, and defended the America's Cup with honor and dignity.
