Skip to main content
Original Issue

Pilloried at the Post

Jimmy Winkfield was America's top jockey, but bigots drove him abroad, where his ride got really wild

by Joe Drape
William Morrow, 280 pages, $24.95

Jimmy Winkfield gave up on his country just before the 1903 Kentucky Derbybegan. The 21-year-old African-American jockey had already won two Derbies andwas clearly the nation's finest rider. Nonetheless, as he guided his mount tothe mark, the starter shouted at him, "You little nigger! Who told you thatyou knew how to ride?"

The insultreminded Winkfield that he was in constant danger at U.S. tracks. The more hewon, the more white Americans despised him: Jockeys bumped and whipped himduring races, trainers were reluctant to hire him because they feared that anattack on Winkfield could result in an injury for their mounts. And so, afterfinishing second in his third--and final--Derby, Jimmy Winkfield set sail forEurope.

Winkfield's lifestory would be worth chronicling if only as a reminder of the enormouscontributions made by African-Americans to the sport of kings. Of the 15jockeys who entered the first Kentucky Derby, in 1875, 13 were black; 15 of thefirst 28 Derbies were won by African-American riders. (Winkfield was the lastto do so, in 1902.) But Drape, a New York Times reporter, doesn't settle fordelivering a sermon on race. Instead, he tells a tale worthy of narration byBaron Munchausen or Forrest Gump.

After Winkfieldleft the States, his first stop was a lush stud farm in Russian-occupiedPoland, where an oil tycoon, attempting to breed the finest horses in EasternEurope, hired Winkfield as his jockey. Despite Russian rules that requiredforeign riders to carry a 10-pound handicap, Winkfield quickly establishedhimself as a jockey without peer. "For us," a Russian horseman wrote inSI in 1961, "Winkfield was like Shoemaker, Arcaro and Longden combined inone." Soon Winkfield, the son of a slave, became fluent in Russian, marriedthe stunning daughter of a military officer and was frequently seen downingcaviar at lavish soirées hosted by the wealthiest aristocrats in the Czar'sempire.

This idylliclifestyle came to a crashing halt in 1917 with the arrival of the Communistrevolution--an event that two years later produced the most remarkableadventure of Winkfield's remarkable life. Fleeing the Bolsheviks, Winkfield anda small group of horsemen set out from Odessa with 260 Russian racehorses. Theytook a circuitous route to Warsaw, through burning villages and smolderingbattlefields littered with rotting corpses. Despite coming under firerepeatedly and nearly starving to death, they lost just 10 horses on their1,100-mile trek.

Unfortunately,Winkfield's devotion to horses was matched by his irresponsible treatment ofhis wife and son, whom he left in Moscow knowing that they would receive harshtreatment from the Communists. Presuming them dead, he moved to France, wherehe established himself as a successful trainer and started a new family. Thenin 1926 his Russian wife, Alexandra, arrived, half-mad, at Winkfield's doorstepwith their 16-year-old son, George. What followed was a tragedy of Gothicproportions: 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 alsostories of how Winkfield escaped Nazi-occupied France in 1941 and returned tothe U.S. with just $9 in his pocket, of how he nearly went blind from drinkingrotgut moonshine, of how an angry mistress shot him in the arm. Drape's writingis not artful, but little art is necessary when a saga is as well researchedand riveting as this one. Winkfield, who died in France at the age of 91, oncesaid, "No matter what kind of life you have, you'll never have a life likemine." He wasn't kidding.



ROSIERTIMES In 1902, aboard Alan-a-Dale, Winkfield was the last black jockey to winthe Derby.