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Pilloried at the Post
Charles Hirshberg
June 26, 2006
Jimmy Winkfield was America's top jockey, but bigots drove him abroad, where his ride got really wild
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June 26, 2006

Pilloried At The Post

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

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BLACK MAESTRO: THE EPIC LIFE OF AN AMERICAN LEGEND
by Joe Drape
William Morrow, 280 pages, $24.95

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. And so, after finishing second in his third--and final--Derby, Jimmy Winkfield set sail for Europe.

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

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 SI 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 soir�es 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. Drape's writing is not artful, but little art is necessary when a saga is as well researched and riveting as this one. 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.

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