Jockey Eddie Arcaro at Keeneland Race Course in April 1953. Arcaro was a Hall of Fame jockey who won more American classic races than any other jockey in history, and he is the only rider to have won the Triple Crown twice, aboard Whirlaway in 1941 and Citation in 1948. He is widely regarded as the greatest jockey in the history of American Thoroughbred horse racing. The Keeneland spring meet concludes this Friday. Herald-Leader Arichive Photo