Nobody in America's Cup history has sailed in the afterguard of more successful Cup boats than Hank Haff, skipper or tactician of four winners between 1881 and 1895. As of 2004, only Nathanael G. Herreshoff, C. Oliver Iselin, and Dennis Conner have matched his remarkable record.
Haff learned to sail while fishing in catboats off Islip, Long Island. His talent as a racing sailor was soon recognized and he rose to the position of "advisor" (tactician) in the afterguard of two America's Cup winners, Mischief in 1881 and Mayflower in 1886. In 1887, he was captain of Mayflower and beat back the dangerous challenger Thistle from Scotland. After serving as skipper of the unsuccessful 1893 defense candidate Colonia, in 1895 he won the Cup again as captain of Defender, crewed by professional fishermen whom he had recruited from Deer Isle, Maine.
The man whom Cup historian Herbert L. Stone called "that foxy old Hank Haff" had a long white beard and was 58 years of age in 1895, making him one of the oldest winning skippers in Cup history. He briefly came out of retirement in 1901 for his sixth America's Cup season as captain of the defense candidate Independence. Two of his sons later sailed aboard Cup defenders.
One of the very best skippers in the generation before Charlie Barr, Hank Haff dominated big boats in a way matched by few captains, before or since, winning the Cup four times in 14 years.