The achievements of African-American jockeys after the Civil War and into the turn of the 20th century are little-known in the annals of horse racing. But nowhere was their proficiency more evident than in their rides in the Kentucky Derby.

Fifteen of the first 28 Kentucky Derbys were won by an African-American horseman with the last win by Jimmy Winkefield, the winner in both 1901 and 1902.

With spots for African-Americans diminishing, Winkefield took his riding career to Europe where it is said he rode for the Czar of Russia. He later bought a horse farm near Paris.

One of the most famous winners was Isaac Murphy, who was the first jockey to win three Kentucky Derbys. He was elected to the National Museum of Racing's Hall of Fame in Saratoga Springs, New York. Dying at age 34 of pneumonia, his body was re-interred in 1977 in the Kentucky Horse Park in Lexington near the grave of Man O'War.

Alonzo "Lonnie" Clayton rode Azra to victory in 1892 winning by a nose to become the youngest jockey to win the Kentucky Derby. He had followed his brother into racing at age 12 starting as an exercise rider. At the time of his victory, he was a mere 15.

Willie Simms won both times he rode in the Derby. Simms is the only African-American jockey to win each of the Triple Crown events.

He is credited with introducing England to short stirrup riding , which puts the rider in a crouching position.