On May 1, 1902, African American jockey Jimmy Winkfield rode Alan-a-Dale to victory, claiming his second straight win at the Kentucky Derby. Winkfield, who had also won in 1901 aboard His Eminence, became one of the few jockeys in history to win the prestigious race in back-to-back years. During the early years of the Derby, Black jockeys dominated the sport—winning 15 of the first 28 races between 1875 and 1902. Despite their early success, systemic racism and exclusion would soon push many African American riders out of the sport. Winkfield’s legacy endures as one of the greatest riders in horse racing history.
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