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Jimmy Winkfield was born on this date in 1882. He was a Black horse jockey.
From Chilesburg near Lexington, KY, he began racing in 1898. Winkfield went from being the youngest of 17 in a family of sharecroppers to racing for $8 a month and eventually, $1,000 a race. His racing statistics show him winning back-to-back Kentucky Derby's, (1901 on His Eminence, and 1902 on Alan-A-Dale). He was the last Black jockey to win a Kentucky Derby.
Blacklisted after he broke a contract with one horse owner by riding for another, Winkfield accepted an offer to race in Russia, where he became a big star again. But by 1917 as the Bolsheviks and the Communists rose to power, racing suffered from its association with wealth and aristocracy. Winkfield led 260 horses, trainers, and owners overland to Poland; a journey the group survived by eating their horses on the way. In Russia, he won the Emperor's Purse, the Moscow Derby twice, and the Russian Derby three times. In Germany, Winkfield won the Grand Prix de Baden. In Poland, he won the Poland Derby twice and in France, he won the Prix du President de la Republique. Winkfield also trained a horse that won the Grand Prix de Paris.
He was married twice. His first wife, Alexandra, was a white-Russian baroness who died in 1920 or '21; they had a son, George who died in 1934. Winkfield’s second wife, Lydia, died in 1958; they had a son, Robert, who died in 1977, and a daughter, Liliane Casey, living in Cincinnati. After his first two Kentucky Derby wins, Winkfield lost his third Derby attempt, and racing itself faltered, plagued by anti-gambling movements and financial hard times. Plus some white jockeys resented the choice mounts and big money earned by successful Black riders. Races became combative; there was even a riot between Black and white jockeys in Chicago.
Winkfield eventually tallied over 2,600 racing victories retiring in 1930 and becoming a horse trainer. During World War II, he returned to South Carolina and worked at an Aiken horse farm, but went back to France in 1953 and lived there to the age of 93. In 1961, 60 years after he first rode to Derby victory, Jimmy Winkfield returned to Louisville for the race and still found recognition and respect elusive. Though he had been invited to a pre-Derby dinner at Louisville's luxurious Brown Hotel, it was still segregated and so the doorman wouldn't let him and his family inside. They were eventually given some seats but nothing as far as recognition of his presence was done.
Jimmy Winkfield died on March 23, 1974, in Maisons-Laffitte, France. His family and supporters pushed for his admission to the Thoroughbred Hall of Fame, so he could join two other Black jockeys already honored there. On August 9, 2004, Winkfield was inducted into the National Museum of Racing and Hall of Fame in Saratoga Springs, NY. The award was presented to his daughter Liliane Winkfield Casey by Edward Hotaling
THE BLOOD-HORSE magazine