The decline and virtual disappearance of African-American jockeys and horse trainers at the turn of the twentieth century presented a sharp reversal from previous decades. A Kentucky native, Winkfield was on the tail end of a long tradition of black horsemen. Following the Civil War, black jockeys and trainers dominated in numbers at southern race tracks as they had during the antebellum era, and the top riders competed against white jockeys in the North. Black jockeys won fifteen of the first twenty-eight Kentucky Derbies beginning in 1875. Isaac Murphy, also from Kentucky, won the Derby three times, as well as every significant race in the United States before his death in 1896. Winkfield won the Derby twice, in 1901 and 1902.
Then Winkfield’s life changed dramatically. During the autumn of 1903, Winkfield went from a rider in high demand to one who could barely line up horses to ride at the New York tracks where he had once known steady success. As Winkfield later explained, he broke a verbal commitment made to one horse owner in New York, opting to ride the horse of another man in the same race. “I got too smart for my pants,” Winkfield later blamed himself. The owner he spurned was John Madden, a powerful man in thoroughbred breeding and racing circles. Madden swore to Winkfield that the jockey would not ride for anyone again in New York;
and, in fact, Winkfield found it harder and harder to find horses to ride. At the same time, thoroughbred racing was becoming a sport almost exclusively for whites, like so much else in the United States. Segregation had received U.S. Supreme Court sanction in Plessy v. Ferguson in 1896. In New York in 1900, white jockeys formed a cabal to try to force black riders off the tracks.
An offer came in 1903 for Winkfield to ride in Russia. He seized the moment, booked passage, and stepped into a new life, acquiring flair and fluency in Russian. Horse racing was the national sport, and Winkfield won its top prizes, including the Russian Derby and the Emperor’s Purse. He became a celebrity. His acquaintances included aristocrats among Czar Nicholas II’s court. He earned an annual income comparable to $100,000 in American dollars. Highly successful in Russia, he also rode with great success in Austria and Germany. Yet the high life did not last. The Bolshevik Revolution of 1917 sent Winkfield and many others to Odessa on the Black Sea, where Russian horse racing tried to carry on as a shadow of its former self. The sport could not continue like this much longer, however. When the Bolsheviks moved their revolution to the Black Sea in 1919, Winkfield had to run once more. In the company of a Polish nobleman and other horsemen, Winkfield fled with two hundred thoroughbreds they hoped to save. During bitter winter months they crossed Moldavia and Romania on horseback, went into Hungary, turned north into Czechoslovakia and crossed part of Poland. They had covered some one thousand miles when finally they reached safe haven at Warsaw with most of the herd; unfortunately, they had to eat some of the horses along the way.
Soon Winkfield received an offer from a former Russian client to ride in France. He resurrected his career once more and rode with notable success. He married the daughter of an expatriate Russian who presented the newlyweds with a three-story chateau and private stables. Frenchmen adored Winkfield. They lovingly called him “le Blackman.” Winkfield spoke French fluently, and became a bon vivant of the Paris racing scene. Eventually, those twin enemies of the jockey profession, age and weight, steered him into a new career as a racehorse trainer in 1930, at age forty-eight.
Eleven years later, Winkfield was on the run again. Adolph Hitler’s troops invaded France in 1940 and for a brief while, Winkfield attempted to tolerate the soldiers who occupied his estate and took over his stables. But he found the Nazis too difficult to accommodate. He sent his daughter and wife to the United States and followed, with his son, in 1941. But he was hardly prepared for what he would find in America.
Winkfield must have been shocked to discover he could work in horse racing only as a stable hand. Jim Crow had changed much in the United States since he had left for Russia nearly forty years earlier. After the war, Winkfield trained some horses for a few clients and a few he was able to purchase. But with segregation and oppression continuing to define race relations in the United States, Winkfield had no prospect of replicating the success he had known in France. He returned to Paris in 1953.
Sports Illustrated interviewed Winkfield in 1961, when he visited the United States, invited by a horse racing journalist to attend a dinner during Kentucky Derby week at the prestigious Brown Hotel in Louisville. But not much had changed in America. At the Brown, a doorman (black like Winkfield) told the former jockey he could not come inside. The reason: This hotel, like most others, was for whites only. Winkfield waited outside for thirty minutes before he was eventually permitted in, only to be shunned by most of the guests. Winkfield promptly returned to France and died there in 1974. In 2004, he was inducted into the National Museum of Racing and Hall of Fame in Saratoga Springs, New York, joining two other African-American jockeys. Winkfield was a man who had seen a world of injustice from the backs of fast horses, yet he seldom looked back on American thoroughbred racing, which had once discarded its black talent to the rank of stable hand.