Eddie Arcaro was one of the greatest jockeys in the history of horse racing, but he rode 250 losers before he won his first race. By the time he retired, Arcaro had racked up 4,779 wins on such famous horses as Whirlaway, Citation, and Kelso. He was also the only jockey in history to ride two Triple Crown champions -- Whirlaway in 1941 and Citation in 1948.