The centrality of horse racing to the culture of the nineteenth-century American South is well understood, but its interplay with the region’s defining institution has become less apparent through time. In Race Horse Men: How Slavery and Freedom Were Made at the Racetrack, historian Katherine Mooney reveals the ways in which the social and professional status of black jockeys and trainers rose and fell with the times, from relatively privileged positions in slavery, to a post-emancipation peak of celebrity, to a devastating collapse with the rise of Jim Crow. In tracing this history Mooney gives us capsule biographies of dozens of horse men, including Jimmy Winkfield, to this day one of only four jockeys ever to win the Kentucky Derby in consecutive years. With this year’s Derby upon us, we’ve excerpted Mooney’s telling of Winkfield’s story below.
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Seasoned bettors figured they knew where to put their money in the 1903 Kentucky Derby. In 1901, nineteen-year-old Jimmy Winkfield had piloted His Eminence to victory. By the end of the year, the young man had established himself as a rider of “good judgment and cold nerve.” In 1902, Winkfield used those qualities in his Derby ride aboard the fragile Alan-a-Dale, a product of the breeding program at Ashland, where the talented young black horse man Courtney Matthews started the colts. Alan-a-Dale went to the lead early, and the other jockeys assumed the delicate-legged horse would fall back at the end. But Winkfield, intimately familiar with Churchill Downs from morning workouts, cagily kept his mount in the light footing along the inside rail, allowing stronger challengers to tire themselves in the deep sand in the middle of the track. When horse and rider went under the wire, Winkfield became the first jockey to win two consecutive Kentucky Derbys since Isaac Murphy in 1890 and 1891, a feat unequalled until Ron Turcotte rode Riva Ridge in 1972 and Secretariat in 1973. By 1903, Winkfield had cemented his reputation on all the tracks in the Midwest and the South, from Chicago to New Orleans. When he sought an unprecedented third Derby win in three years, Louisville railbirds knew to watch his mount, Early, the property of veteran Midwestern horse man Patrick Dunne.
Turning for home, Winkfield took Early to the lead but left space on the rail for the long shot Judge Himes, ridden by a first-time Derby competitor, the white jockey Henry Booker. When Judge Himes slipped through the hole, Early could not hold him off. After the race, Winkfield, surrounded by reporters, slumped against the wall of the jockeys’ room and wept. Booker, recounting his victory, told the newspapermen about the moment he had brought his horse up even with Early: “Winkfield turned around at me and laughed. It was then that I was sure I did not have a chance. That nigger, I was sure, was trying to make a sucker out of me.” But Early did not have enough stamina to withstand the challenge, and Booker brought his horse surging to the lead. “I have got that nigger beat,” Booker recalled his thoughts for the writers. His grim satisfaction suffused his words. Jimmy Winkfield never rode in another Kentucky Derby, not because his skill had failed him, but because the track itself was changing profoundly, in ways that resounded in Booker’s well-publicized bigotry.
The youngest in a family of seventeen children, Jimmy Winkfield grew up in the all-black hamlet of Chilesburg, Kentucky, a few miles east of Lexington. His father George, almost fifty when Jimmy was born, had joined up with the U.S. Colored Troops at Camp Nelson in 1865. Jimmy was a member of the first free generation of his family. But Winkfield was still barely a teenager, doing odd jobs and hanging around the racetrack, when Isaac Murphy died in 1896. In 1897, he began his career as a rider, and by 1903 he had made his mark decisively, despite his disappointing Derby loss.
The formidable John E. Madden, one of the nation’s most successful owners, saw the rising young jockey at the New York tracks and gave Winkfield his seal of approval and a contract to ride his The Minute Man in the Futurity at Sheepshead Bay. Winkfield had come east to ride for Lexington horse man Bub May, but Madden’s offer was a tempting ticket to the highest peak of his profession. As the jockey later told it, he took Madden’s money and then accepted an additional $1,000 from May to stay with his original employer for the race. Enraged at being used, Madden informed the young man that he would never ride at top-class American tracks again. Six months after his loss with Early, Winkfield signed a contract to ride in Europe in the 1904 season. “They gave me a book so I could learn Polish,” he remembered decades later, “and I rode two winners on opening day in Warsaw.” He was hardly the only American on the tracks of Poland, Russia, Germany, and France, where black and white riders from the United States migrated in search of higher weight limits and bigger paychecks. But, even in cosmopolitan company, Winkfield stood out. In 1904, he captured the Warsaw Derby and began his ascent as one of Europe’s premier jockeys. Horsemen recognized talent when they saw it, and the bettors of eastern Europe put their money down on Winkfield’s mounts, making “him a favorite even though he’d be riding a goat.”
Winkfield came home to Kentucky each winter, still trying to pick up a contract in the United States, near his family, including the wife he had left in Lexington. But he was fighting a rising tide of sentiment against black riders and trainers. “I know that just race prejudice keeps me out of my country,” he told one African American newspaper in frustration. The American racetrack that Jimmy Winkfield had seen as a teenager, the one on which Isaac Murphy had been a troubled hero, was inexorably changing. Ultimately, he gave up trying to find a place on it. By 1910, when he changed employers in Europe, boosting his contract by $2,000 annually, he no longer publicly expressed any desire to ride in the United States. In 1911, his wife sued for divorce, citing abandonment. Testifying in the case, which Winkfield did not contest, his sister Maggie answered a lawyer’s question about where her brother was. “He’s with the horses,” she answered simply. Generations of men before him had followed the animals and the opportunities they brought, but now staying with them meant leaving the United States behind.
Winkfield’s career soared, as European horsemen recognized his skills and accepted him as one of their own. When the Russian Revolution broke out, he was living in an apartment opposite the Kremlin with a white valet, ensconced in luxury purchased with his princely salary. Escaping ahead of Bolsheviks unsympathetic to a man who made an opulent living piloting the playthings of the rich, Winkfield and a large group of horsemen took refuge in Odessa, where a track still operated. But he knew his safety was only temporary. “This ain’t no longer a place,” he recalled his thoughts on the subject, “for a small colored man from Chilesburg, Kentucky to be.” Packing up women, children, and 262 of the finest horses still to be found in war-torn Europe in 1919, Winkfield and his backstretch colleagues walked for three months through 1,100 miles of hostile territory to safety in Poland. It was an epic journey, on which only ten animals were lost, the lack of casualties a tribute to the skill and experience of the horsemen in charge.
From Poland, Winkfield continued on to Paris, where he established himself as the darling of French tracks, known to adoring spectators as le blackman, the winner of some of the greatest races on the Gallic turf. After 1930, when he rode the last of more than 2,300 winners, he trained at his own stable in the equine colony of Maisons-Laffitte, where he resided in comfort with his Russian wife, their children, and his in-laws. At the Winkfield home, African American expatriates and visitors always found a warm welcome. Josephine Baker and Bill “Bojangles” Robinson danced in the living room for parties of friends. With the coming of the Nazi occupiers, the Winkfields quickly fled to the United States. Jimmy carried nine dollars in his pocket. They spent World War II in America, Winkfield wearing French suits to the track, concealing his connection with his white wife, and counseling patience to his son Robert, who was unaccustomed to American racial codes. In 1953, the family returned to France.
In 1961, Winkfield came to the United States for an operation, explaining that if he were going to die, he wanted to die in Kentucky. A Sports Illustrated reporter, catching wind of the visit, profiled the old man and drew national attention to him. Following successful surgery, the resurgent horse man decided to attend his first Kentucky Derby in nearly sixty years. Sports Illustrated invited Winkfield and his daughter Liliane to a dinner at Louisville’s Brown Hotel during Derby week, but the two nearly missed the occasion, when the doorman, himself black, denied them entrance to the hotel because of their race. Winkfield, however, could not be kept away from the Derby, where he sat with his old friend, the white jockey Roscoe Goose, wearing a fedora, smoking a cigar, and watching the runners with a joyously knowing eye. When the entries came on the track for the Derby to the strains of “My Old Kentucky Home,” he wept openly. Forty years later, Liliane Winkfield Casey explained the emotions that had welled up that day. “My father loved that song,” she said. “To him, that was the national anthem.” It was the national anthem of an America of racetracks where a black man could comfortably support his family and know that his children could have the lives he wanted for them. But Jim Crow had changed that country beyond recognition.
