Does character make a difference in the meaning of greatness? In addition, how much do you factor in regional versus national success?
No. 10: Jacinto Vasquez. 5,231 career wins. The first American jockey to ever win 5,000 races. Among those, Kentucky Derby winners, Foolish Pleasure in 1975, and Genuine Risk in 1980. Vasquez might have been the greatest rider of fillies in American history, guiding great filly Ruffian for her entire career, as well as Princess Rooney--winner of the first Breeders' Cup Distaff.
No. 5: Gary Stevens. 4,888 career wins. Winner of the prestigious George Woolf Memorial Jockey Award in 1996, the always affable yet competitive Stevens won eight Triple Crown races, coming the closest to winning the entire Triple Crown in 1997 aboard Silver Charm. Stevens also won seven Breeders' Cup races. Today he is a horseracing analyst for HRTV and NBC Sports.
No. 3: Eddie Arcaro. 4,779 career wins. A fierce competitor, a great judge of pace, and a strong finisher on a horse, the six-time winner of the United States Champion Jockey by earnings, won more American Classic Races than any other jockey in history, and is the only rider to have won the Triple Crown twice -- in 1941 on Whirlaway and again in 1948 on Citation. He is tied with Bill Hartack for most Derby wins at five, and has the most wins in the Preakness Stakes and the Belmont Stakes with six.