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.
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.