On August 10, 1898, Winkfield rode his first race. Aboard Jockey Joe at Chicago's Hawthorne Racetrack, he raced his horse out of the gate and rode across the path of the three inside horses, in an effort to get to the rail. This aggressive behavior did not go over well with racetrack officials and he earned a one year suspension. Winkfield learned from his mistake and on September 18, 1899, won his first race. Six months later he rode for the first time in the Kentucky Derby.
In 1901, at 19, Winkfield captured his first Kentucky Derby title astride a horse named Eminence. He went on to win 161 races that year, including key victories in the Latonia Derby on Hernando and Tennessee Derby where he rode Royal Victor. While these were spectacular accomplishments, he returned to the Kentucky Derby in 1902 and won again in the most important race of his career.
In 1903, Winkfield narrowly missed winning a third consecutive Derby. Had he accomplished this feat, he would be the first (and only person) to have ever done so. Riding a thoroughbred named Early, the odds-on favorite, Winkfield, took a 1 1/2-length lead but his mount slowed in the stretch and lost by three-quarters of a length. Winkfield called the loss the worst of his career.
Blacklisted after he dishonored a contract with one horse owner by riding for another, Winkfield accepted an offer to race in Russia, where he rose to fame once again. 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 continued to race throughout Europe while living in Moscow. When the Communist Party came to power in Russia in 1919, horse racing was outlawed. Winkfield, now a trainer, led 260 horses, fellow trainers and owners overland to Poland during the winter of 1920. During this arduous journey the group survived by eating some of their horses on the way.
Winkfield married twice. His first wife, Alexandra, was a Russian baroness who died in 1921.They bore a son, George who died in 1934. His second marriage was to a French woman named Lydia who died in 1958. This marriage also produced a son, Robert, who died in 1977 and a daughter, Liliane Casey, who currently resides in Cincinnati, Ohio.
Jimmy Winkfield died on March 23, 1974 in Maisons-Laffitte, France. His family and supporters lobbied for his admission to the Thoroughbred Hall of Fame, so he could join two other African-American jockeys who had already been honored there. On August 9, 2004, Winkfield was inducted into the National Museum of Racing and Hall of Fame in Saratoga Springs, New York. The award was presented to his daughter Liliane Winkfield Casey by Edward Hotaling, President of the Museum.
Ed Hotaling, Wink: the Incredible Life and Epic Journey of Jimmy Winkfield (New York: McGraw-Hill, 2004); Neil Schmidt, “Black Jockey’s journey spanned different worlds.” The Cincinnati Enquirer. April 29, 2002.
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