Winkfield raced in the United States from 1899 to 1904. He won 161 races in 1901 alone. When Jim Crow injustice finally reached the racetracks, like many other African American jockeys, it eventually forced him off the tracks. Winkfield was the last Black jockey to win the Kentucky Derby (in 1902—he won two Derbies) until a Black jockey reentered the racing scene in the early 2000s.
After death threats from the Ku Klux Klan and damage to his reputation for jumping a contract, Winkfield left the US for czarist Russia in 1904. There his riding skills gave him celebrity and fortune beyond anything he could imagine in the States. He stayed until he had to flee the Bolshevik Revolution in 1917, landing in France to race for another decade until he retired with over 2,600 wins.
Yet again in 1940, he had to flee established success when his stables were seized by Nazis. He returned to the Unites States and signed onto a Works Progress Administration road crew.
In 1953 he left again for France and opened his own training school for jockeys. He returned once more to the States in 1961 to attend the Kentucky Derby. He and his daughter were denied entry to a pre-Derby banquet at Louisville’s historic Brown Hotel. Only after the hotel management confirmed they were guests of Sports Illustrated were they allowed to attend. Winfield lived in France until his death in 1974.
In this photo, taken in 1901, Winkfield is shown on Martimas, in Washington Park in Chicago.
For further reading about Jimmy's life and acheivements, as well as more information about other Black jockeys, please follow this link to an article from the Smithsonian Magazine.