The Epic Journey of James ‘Wink’ Winkfield

Jimmy Winkfield aboard 1902 Kentucky Derby victor Alan-a-Dale. (Churchill Downs photo)

He was on the doorstep of becoming America’s greatest black race rider. One of just five men to win back-to-back Kentucky Derbys (1901-1902), he barely missed a third victory the following year.

But, the story of James “Wink” Winkfield being a great jockey would just be a slice of his existence. Has any jockey led a more incredible life?

In the early 1900s, a combination of big money, violence by white jockeys, even intimidation from the Ku Klux Klan was forcing the great African-American jockeys from the racing game. A professional jockey for just five years, Winkfield bought a steamer ticket and headed for Russia with nothing but a Russian/Polish/English dictionary in late 1903. He regularly rode winners in Russia, Poland, France, Austria, Hungary, England, Spain, and Italy, ultimately winning nearly every marquee race on the continent. He was celebrated in the sports pages, and the gossip pages, too.

In 1919, Winkfield escaped the Bolshevik’s thundering cannon fire leading 250 top-tier Thoroughbreds, Polish noblemen, and horsemen on a harrowing 1,100-mile journey to a safe haven in Warsaw.

Winkfield resurrected his career in France in 1922. His father-in-law presented the newlyweds with a three-story chateau and private stables in the lush countryside outside Paris. When the Nazis stormed the property in 1941, Winkfield defended himself with a pitchfork. Returning home to America 60 years after his first Kentucky Derby victory, Winkfield found his legend at home all but forgotten.

Born in Chilesburg, Ky. in 1880, Winkfield was the youngest of 17 children in a family of sharecroppers. The son of a slave, as a youngster Winkfield split his time between daily chores on the farm and eyeing the strings of Thoroughbreds that paraded down the farm's dusty lane. He observed the ways of gifted horsemen by watching through the fences that dotted the Bluegrass horse country.

Winkfield dreamed of becoming a jockey and following in the footsteps of prominent black riders like Isaac Murphy, who in 1891 became the first jockey to capture successive Kentucky Derbys and would go to win a third. At age 15, Winkfield left the farm to work as a stable hand at Latonia Racetrack, and progressed to exercising horses. He earned $8 a month and board.

“I was rich,” he later boasted.

Jimmy Winkfield (Smithsonian photo)

Winkfield went to post the first time piloting Jockey Joe at Chicago’s Hawthorne Racetrack. It was a disaster. In the book “The Kentucky Derby: The First Hundred Years” author Peter Chew described the scene: “Breaking fourth from the rail, he cut straight across the path of three inside, trying to get to the rail — and all four horses went down. The stewards put Winkfield down too, for a year."

Winkfield reached the Kentucky Derby in 1900 with Thrive and finished third. He returned in 1901, guiding His Eminence across the finish line first. He repeated the feat in 1902 with Alan-a-Dale. He rode Early in the 1903 edition, finishing second by three-quarters of a length. No jockey has topped his Derby record. In four appearances he won two and finished second and third in the others.

Just 21, Winkfield was a cocky and daring rider who was very much in demand. Then, his life changed dramatically. "Wink" broke a verbal commitment made to the powerful Thoroughbred owner John Madden, opting to ride the horse of another man in the same race. Madden swore that the jockey would not ride for anyone again in New York. At the same time, race riding was becoming almost exclusively for whites.

When an offer came to ride in Czarist Russia, Winkfield travelled to Europe and went on to Russia. European noblemen and wealthy oil barons owned top-tier horses that competed at Moscow and St. Petersburg racetracks. Winkfield won the multiple editions of the Moscow Derby, including aboard four-time victor Bahadur, and competed with great success in Austria and Germany over the years.

Winkfield earned a king's ransom, $100,000 annually. He purchased a suite in Moscow's luxurious National Hotel, where he employed a white valet. He ate caviar for breakfast and drank vintage bottles of wine. His circle of friends included millionaires and aristocrats in Czar Nicholas II’s court.

Winkfield’s high life didn’t last. By 1917, the Bolsheviks and the Communists had risen to power and racing was being shut down. Winkfield and his racing community moved to Odessa on the Black Sea. But soon, Winkfield was once again on the run.

He led 250 Thoroughbreds, Polish noblemen and horsemen overland across the Transylvania Alps to Poland. There was no food, and villagers robbed them. During the three-month nightmarish odyssey they survived by eating some of the horses. Today, the bloodlines of some of those same horses Winkfield saved are some of the greatest stallions in Europe.

After jump-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 of Paris. He spoke French fluently, became a bon vivant of the Paris racing scene and shared the limelight with the likes of Ernest Hemingway, Josephine Baker, and royalty from around the world.

By age 48, the physical toll of riding forced him to retire, but Winkfield launched a successful training career in 1930. A decade later, when Adolph Hitler’s troops invaded France, they requisitioned all his horses, his stables, and his house. Winkfield fled once more, this time back to America.

Hardly anyone knew or cared about his racing history. The only job he got in racing was as a groom. Fed up with the second-class citizen status, Winkfield returned in 1953 to Maisons-Laffitte, where he operated one of the most successful racing stables through the 1950s and 1960s.

In May 1961, Winkfield returned to the United States for one last 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 to honor the two-time winner at the luxurious Brown Hotel in Louisville, Ky. Still segregated, the black doorman wouldn’t allow Winkfield to enter through the front door. Winkfield stood his ground. Eventually they were admitted. The banquet guests ignored them.

That is, except for Roscoe Goose. A white jockey, Goose had won the 1913 Derby on Donerail, who at 91-1 was the longest price winner in Derby history. He recognized Winkfield and sat at his table. Three days later they met again on Derby day. "Wink" was dressed in a dapper, pin-striped suit, and sported a Fedora. They smoked cigars and told stories to the hometown reporters.

When Winkfield had earned enough money, he travelled back to Maisons-Laffitte. In his later years, he walked torturously with the aid of two canes, exercising a body that had lived almost 92 years. He passed away on March 23, 1974, and was buried in the town cemetery. It closed the book on a life and career, one of the most fantastic of the 20th century.

Thirty years after Winkfield died he received his due. He was inducted into the U.S. Racing Hall of Fame, its third African-American jockey. The award was presented to his daughter Liliane Winkfield Casey. Every year, Aqueduct stages the six-furlong Jimmy Winkfield Stakes on the third Monday of January, Martin Luther King Day — 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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