Born 1882, in Chilesburg, KY, Jimmy Winkfield had one of the most storied careers of all.
Jimmy Winkfield was one of only four jockeys in history to win back-to-back runnings of the Kentucky Derby, scoring on “His Eminence” in 1901 and “Alan-a-Dale” in 1902. Known as the king of the Chicago tracks, he was described by Col. Phil Chinn as a “gentleman on the ground, a demon in the saddle.” Wink, as he was called, won 220 races in 1901 including the Clark Handicap, Tennesee Derby, Latonia Derby, and New Orleans Derby. But Wink was not allowed to continue his dominance at home.
Jimmy Winkfield gave up on his country just before the 1903 Kentucky Derby began. The 21-year-old African-American jockey had already won two Derbies and was clearly the nation’s finest rider. Nonetheless, as he guided his mount to the mark, the starter shouted at him, “You little nigger! Who told you that you knew how to ride?”
The insult reminded Winkfield that he was in constant danger at U.S. tracks. The more he won, the more white Americans despised him: Jockeys bumped and whipped him during races, trainers were reluctant to hire him because they feared that an attack on Winkfield could result in an injury for their mounts.
An Anti-Colored Union was in place, with the goal of running the black riders off the racetrack. It had begun earlier in the year at the Queens County track when the white jockeys…put the word out that if owners wanted to take home first-place purses, they’d best not ride the colored jockeys…Sometimes [the white jockeys] pocketed, or surrounded, a black jockey until they could ride him into and over the rail. Their whips found the thighs, hands, and face of the colored boy next to them more often than the horse they were riding. Every day a black rider ended up in the dirt; and every day racing officials looked the other way.
And so, after finishing second in his third–and final–Derby, Jimmy Winkfield set sail for Europe.
(and POU…this is where the story gets VERY interesting!)
After Winkfield left the States, his first stop was a lush stud farm in Russian-occupied Poland, where an oil tycoon, attempting to breed the finest horses in Eastern Europe, hired Winkfield as his jockey. Despite Russian rules that required foreign riders to carry a 10-pound handicap, Winkfield quickly established himself as a jockey without peer. “For us,” a Russian horseman wrote in Sports Illustrated in 1961, “Winkfield was like Shoemaker, Arcaro and Longden combined in one.” Soon Winkfield, the son of a slave, became fluent in Russian, married the stunning daughter of a military officer and was frequently seen downing caviar at lavish soirees hosted by the wealthiest aristocrats in the Czar’s empire.
This idyllic lifestyle came to a crashing halt in 1917 with the arrival of the Communist revolution–an event that two years later produced the most remarkable adventure of Winkfield’s remarkable life. Fleeing the Bolsheviks, Winkfield and a small group of horsemen set out from Odessa with 260 Russian racehorses. They took a circuitous route to Warsaw, through burning villages and smoldering battlefields littered with rotting corpses. Despite coming under fire repeatedly and nearly starving to death, they lost just 10 horses on their 1,100-mile trek.
Unfortunately, Winkfield’s devotion to horses was matched by his irresponsible treatment of his wife and son, whom he left in Moscow knowing that they would receive harsh treatment from the Communists. Presuming them dead, he moved to France, where he established himself as a successful trainer and started a new family. Then in 1926 his Russian wife, Alexandra, arrived, half-mad, at Winkfield’s doorstep with their 16-year-old son, George. What followed was a tragedy of Gothic proportions: Alexandra died in an insane asylum eight years later, and George, after showing promise as a jockey, was fatally stabbed in a fight.
There are also stories of how Winkfield escaped Nazi-occupied France in 1941 and returned to the U.S. with just $9 in his pocket, of how he nearly went blind from drinking rotgut moonshine, of how an angry mistress shot him in the arm. In 1961, six decades after winning his first Kentucky Derby, Winkfield returned to Kentucky to attend a pre-Derby banquet. When he and his daughter Liliane arrived at Louisville’s historic Brown Hotel, they were denied entry. After a long wait and repeated explanations that they were guests of Sports Illustrated, they were finally admitted.
Winkfield, who died in France at the age of 91, once said, “No matter what kind of life you have, you’ll never have a life like mine.” He wasn’t kidding.
In 2004, Winkfield was inducted into the Racing Hall of Fame, and the following year, the New York Racing Association named a race in his honor, run each year on the Martin Luther King, Jr. holiday. The Jimmy Winkfield Stakes, the only race run today that commemorates the contributions and accomplishments of African-Americans in racing.
From: BLACK MAESTRO: THE EPIC LIFE OF AN AMERICAN LEGEND by Joe Drape