From 1875 to 1902, black jockeys rode 15 of the first 28 winners of the Kentucky Derby, the most prestigious horse race in America. In the first Derby race, all but one of the riders was black, including the winner, Oliver Lewis, who rode a horse named Aristides. The trainer of the triumphant horse was also black.
Seventeen years later, the 90-pound Clayton rode Azra to victory, making up six horse lengths to edge two other contestants at the finish. Clayton would later ride Azra to victories in the Champagne Stakes, Clark Handicap, and Travers.
Competing in three later Kentucky Derbys, Clayton finished second twice and third once. His career effectively ended when he was arrested for allegedly fixing — that is, taking money to intentionally lose — a race in 1901. Charges were dismissed, but the racist backlash against black jockeys in the 1900s made riding opportunities scarce.
Clayton worked as a bellhop in a California hotel before dying of tuberculosis at age 40 in 1917.
The best African-American jockey — possibly the best of any race — was Isaac Murphy, the first person to ride three Kentucky Derby winners. Murphy won in 1884 aboard Buchanan, in 1890 aboard Riley, and in 1891 aboard Kingman. His 44 percent winning rate is the highest of any jockey.
Jimmy Winkfield was the last African-American jockey to ride a Kentucky Derby winner. He won back-to-back Derbys in 1901 and 1902 before racist laws prevented black jockeys from competing with whites in most major U.S. horse races.