A native of Chilesburg, Kentucky in Lexington’s Bluegrass Country, Jimmy Winkfield began his work with horses in the late 1890s. He had a short racing career in the United States, lasting from 1898 to 1903. However, he won many premier stakes races such as the Latonia Derby in Northern Kentucky, the Tennessee Derby in Nashville and the Clark Handicap at Churchill Downs. Most importantly, he won the Kentucky Derby twice, 1901 and 1902, and is the most recent Black jockey to win the celebrated race.
Due largely to segregation, Winkfield eventually left the United States to ride overseas. He had a successful riding career in countries such as Russia and France. He retired from race riding in 1930 and managed a racing stable with his family in the town of Maisons-Lafitte. In 1940, the Nazi forces occupied France and eventually seized the family’s property. They fled to the United States for safety. Winkfield worked several odd jobs in the equine industry, eventually trained a few horses and returned to France in 1953.
Winkfield returned to the United States in 1961 for surgery. After a successful operation, Winkfield was invited to attend a 1961 pre-Derby celebration at the Brown Hotel in Louisville. Because of his race, Winkfield was initially refused admission through the front door. Through much discussion, Winkfield was finally allowed to attend the celebration. He returned to Maisons-Lafitte and continued working with the horses in his stable until his death in 1974 at the age of 91. He was posthumously inducted into Thoroughbred Racing’s Hall of Fame in 2004.