But the story that James “Wink” Winkfield was a great jockey would be only part of his existence. Has a jockey lived a more incredible life?
In the early 20th century, a combination of big money, violence by white jockeys, and even intimidation by the Ku Klux Klan forced major African-American jockeys out of racing. A professional jockey for only five years, Winkfield bought a steamboat ticket and left for Russia in late 1903 with nothing but a Russian/Polish/English dictionary. He regularly rode winners in Russia, Poland, France, Austria, Hungary, England, Spain and Italy, eventually winning almost every major race on the continent. He was celebrated on the sports pages, but also on the gossip pages.
In 1919, Winkfield escaped the thunderous cannon fire of the Bolsheviks and led 250 top-level Thoroughbreds, Polish noblemen and horsemen on a harrowing 1,100-mile journey to a safe haven in Warsaw.
Winkfield revived his career in France in 1922. His father-in-law gave the newlyweds a three-story castle and private stables in the lush countryside outside Paris. When the Nazis stormed the building in 1941, Winkfield defended himself with a pitchfork. When he returned to America 60 years after his first victory in the Kentucky Derby, Winkfield found his legend all but forgotten at home.
Born in Chilesburg, Kentucky in 1880, Winkfield was the youngest of 17 children in a family of sharecroppers. The son of a slave, as a youth Winkfield divided his time between daily farm chores and watching the strings of thoroughbreds parade down the farm’s dusty street. He observed the manners of gifted horsemen by looking through the fences that dotted the Bluegrass horse country.
Winkfield dreamed of becoming a jockey and following in the footsteps of prominent black riders such as Isaac Murphy, who in 1891 became the first jockey to capture consecutive Kentucky Derbys and would win a third. At the age of 15, Winkfield left the farm to work as a groom at the Latonia Racetrack, and continued training horses. He earned $8 a month and board.
“I was rich,” he later boasted.
Winkfield posted the first time he piloted Jockey Joe at Hawthorne Racetrack in Chicago. It was a disaster. In the book “The Kentucky Derby: The First Hundred Years,” author Peter Chew described the scene: “When he broke the rail in fourth, he crossed straight across the path from three to the inside, trying to reach the rail – and all four horses went down. The stewards also put Winkfield down for a year.”
Winkfield reached the Kentucky Derby in 1900 with Thrive, finishing third. He returned in 1901 and led His Eminence across the finish line first at Churchill Downs. He repeated this feat in 1902 with Alan-a-Dale. He raced early in the 1903 edition and finished second by three-quarters of a length. No jockey has surpassed his Derby record. In four appearances he won two and finished second and third in the other.
Winkfield, still only 21, was a stubborn and daring rider who was in high demand. Then his life changed dramatically. “Wink” broke a verbal commitment to powerful Thoroughbred owner John Madden, who chose to ride another man’s horse in the same race. Madden vowed that the New York jockey would not ride for anyone again. At the same time, racing became almost exclusively the preserve of white jockeys.
When an offer came to ride in Tsarist Russia, Winkfield traveled to Europe and then went to Russia. European noblemen and wealthy oil barons owned top-level horses that competed in the racecourses of Moscow and St. Petersburg. Winkfield won multiple editions of the Moscow Derby, including aboard four-time winner Bahadur, and competed with great success in Austria and Germany over the years.
Winkfield earned a king’s ransom, $100,000 a year. He bought a suite in the luxurious National Hotel in Moscow, where he hired a white servant. He ate caviar for breakfast and drank vintage bottles of wine. His circle of friends included millionaires and aristocrats from the court of Tsar Nicholas II.
Winkfield’s good life did not last long. In 1917 the Bolsheviks and the Communists had come to power and racing was stopped. Winkfield and his racing community moved to Odessa on the Black Sea. But soon Winkfield was on the run again.
He led 250 thoroughbreds, Polish noblemen and horsemen overland through the Transylvanian Alps to Poland. There was no food and villagers robbed them during the three-month nightmarish odyssey. Today, the bloodlines of some of those same horses Winkfield rescued are among the greatest stallions in Europe.
After kick-starting his riding career in Poland, a former Russian patron brought Winkfield to France in 1922. There Winkfield married his third wife, Lydia de Minkiwitz, a Russian baroness, and launched a racing stable in the historic town of Maisons-Laffitte, 11 miles outside Paris. Fluent in French, he became a bon vivant of the Parisian racing scene and shared the spotlight with the likes of Ernest Hemingway, Josephine Baker and royalty from around the world.
At the age of 48, the physical toll of riding forced him to retire, but Winkfield embarked on a successful training career in 1930. Ten years later, when Adolf Hitler’s troops invaded France, they claimed all his horses, his stables and his house. Winkfield fled again, this time back to America.
Almost no one knew or cared about his racing history. The only job he got in racing was as a groom. Fed up with his second-class status, Winkfield returned to Maisons-Laffitte in 1953, where he operated one of the most successful racing stables in the 1950s and 1960s.
In May 1961, Winkfield returned to the United States for a final visit to attend the Kentucky Derby for the first time since 1903. Winkfield and his daughter Liliane were invited to a reception hosted by Sports illustrated honoring the two-time winner at the luxurious Brown Hotel in Louisville, Kentucky. Still separated, the black doorman would not let Winkfield enter through the front door. Winkfield stuck to his guns. Finally they were admitted. The banquet guests ignored them.
That is, except for Roscoe Goose. Goose, a white jockey, had won the 1913 Derby on Donerail, who at 91-1 was the longest prize winner in Derby history. He recognized Winkfield and sat down at his table. Three days later they met again on Derby day. “Wink” was dressed in a sharp pinstriped suit and wore a Fedora. They smoked cigars and told stories to their hometown reporters.
When Winkfield had earned enough money, he traveled back to Maisons-Laffitte. In his later years he walked torturously with the help of two sticks, training a body that had lived for almost 92 years. He died on March 23, 1974 and was buried in the city cemetery. It closed the book on a life and career one of the most fantastic of the 20th century.
Thirty years after Winkfield’s death he received his due. He was inducted into the US Racing Hall of Fame, the third African-American jockey. The award was presented to his daughter Liliane Winkfield Casey. Every year Aqueduct hosts the six-furlong Jimmy Winkfield Stakes – a fitting tribute to the last black jockey to win the Kentucky Derby.
Note: This article was originally published in September 2014.
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