With this year’s Kentucky Derby ensconced in the history books, I wanted to chronicle the extraordinary life of Jimmy Winkfield the last African-American jockey to win the Kentucky Derby.
Winkfield was born in 1882 in Chilesburg, Kentucky, a small town outside of Lexington. He was the youngest of 17 children in a family of sharecroppers. Working first as a shoe shine boy, he became a stable hand and then progressed to exercising horses. Finally at the age of sixteen he was given his chance to race.
Wink began his career as a jockey in 1898 riding a horse named Jockey Joe at Hawthorne Race Track. Gunning his mount out of the gate, he crossed the paths of three other rivals in his zeal to reach the rail. His aggressive riding style didn’t endear him to the stewards that day and they handed Wink a one year suspension. Chastened he returned in the fall of 1899 to ride his first winner.
Six months later found him finishing third on Thrive in the 1900 Kentucky Derby. In 1901, at the age of 19, Wink captured his first Kentucky Derby on His Eminence. He went on to win 220 races that year, including victories in the Latonia Derby on Hernando and the Tennessee Derby on Royal Victor.
He returned to Louisville in 1902 to claim a second Kentucky Derby on Alan-A-Dale. The following year he narrowly missed winning a third consecutive Derby. Had he done so, he would have been the first jockey to have accomplished this feat. Riding Early, the odds-on favorite, Winkfield, took a 1 1/2-length lead but was passed in the stretch by Judge Himes. He would consider this loss the worst of his career.
Winning back to back runnings of the Kentucky Derby put him in rarified company as Wink joined Isaac Murphy as only the second jockey to achieve this. It wouldn’t be duplicated again until 1967 when Bobby Ussery rode Proud Clarion and Dancer’s Image the following year.
With the advent of the Jim Crow Laws in 1903, Wink was blacklisted for breaking a contract with one horse owner by riding for another. Accepting an invitation from Tsar Nicholas II to race in Russia, Wink quickly rose to fame. He won the Emperor's Purse, the Moscow Derby twice, the Russian Derby three times and the Russian Oaks five times.
Wink won important races throughout Europe including two runnings of the Poland Derby and Germany’s Grand Prix de Baden.
In Czarist Russia, Wink won their national riding championship an unheard-of three times. He became fabulously wealthy and married a Russian Baroness. But the advent of the Russian Revolution of 1917 forced the entire horse racing community south to Odessa on the Black Sea.
In 1918, as the Red Army was closing in on Odessa and burning down the racetrack, Wink and his fellow riders, trainers and owners drove 250 thoroughbreds across the Transylvanian Alps to Poland - a thousand-mile odyssey - eating horseflesh to survive.
He left Poland and settled in France in 1922 where he resumed riding and resurrected his career. His numerous wins included the Prix du Président de la République, Grand Prix de Deauville, and the Prix Eugène Adam. He retired as a jockey at age fifty having won more than 2,500 races and then began a second successful career as a horse trainer.
Winkfield lived on a farm near the Hippodrome de Maisons-Laffitte (racetrack) in Maisons-Laffitte on the outskirts of Paris. By 1940 he was training horses as the Nazis occupied France. When German soldiers commandeered his property and confronted him at his own stables, Wink defended himself with a pitchfork. Once again, Wink was forced to flee in the face of historic catastrophe.
During World War II Winkfield returned to the United States and worked as a groom. In 1953 he went back to France and opened a school for training jockeys with his son, Robert. Wink lived in France until his death in 1974.
While being treated with respect in Europe, segregation still ruled American society. Sports Illustrated invited Winkfield in 1961 as a two-time winner, to a Kentucky Derby banquet. But when he and his daughter arrived at Louisville's historic Brown Hotel, they were told they couldn't use the front door; after a long delay they were let in, but most people at the banquet ignored them. Except for an old competitor. Jockey Roscoe Goose, who rode Donerail to victory in 1913, recognized Jimmy even though he hadn't seen him since their Derby days sixty years earlier, came over, introduced himself, and sat down next to him.
One of the last public photos of Jimmy, was taken at the Kentucky Derby the following day. He was sitting next to his old rival Roscoe, both in suits and hats, smoking cigars, smiling and telling stories to incredulous reporters. Wink had not only outrun his competition on the racetrack but he’d outrun racism once again.
Jimmy Winkfield was inducted into the Racing Hall of Fame in 2004. The following year, the United States House of Representatives passed a resolution honoring Jimmy Winkfield. A race is named in his honor and is run at Aqueduct Race Track.