Jimmy Winkfield, born on April 12, 1882, became famous as an early 20th Century horse jockey.  Winkfield, the youngest of 17 children, was born in Chilesburg, Kentucky, a town just outside of Lexington.  As a child, he had a routine that included performing chores on the farm where his father was a sharecropper and overseeing the thoroughbred parades down the country roads. He and his family moved to Cincinnati in 1894.

On August 10, 1898, Winkfield rode his first race. Aboard Jockey Joe at Chicagos 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 Emperors 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