Jockey Jimmy Winkfield Two-time Derby winner found acceptance, respect in Europe

By Mark Coomes

The last black jockey to win the Kentucky Derby struck the finish line 100 years ago.

The victory was tiny Jimmy Winkfield’s second straight in America’s greatest horse race, a feat matched by only three other riders.

Winkfield’s victories, in 1901 and 1902, were merely another implausible milestone in what might be the most far-fetched life and far-flung riding career in the history of thoroughbred racing.

Played out in New York, Moscow, Warsaw, Paris and back, the picaresque life of Jimmy Winkfield is an exuberant epic of contradictions.

Born in a Kentucky sharecropper’s shack, he died in a French chateau. He rode for Polish princes, German barons and Armenian oil tycoons — and against the last czar of Russia.

Old age claimed him when Bolshevik bullets, Nazi occupation and threats from the Ku Klux Klan couldn’t.

He drank tainted moonshine that literally crossed his eyes, but he won 2,000 races using that peculiar stare.

He had his own suite at Moscow’s best hotel but couldn’t have rented a cot at Louisville’s Seelbach or Brown.

”If Mr. Winkfield’s life were a jigsaw puzzle,” his friend Marjorie Weber wrote in 1971, ”the Derby would be only one small piece.”

Denied mounts in America because of his race, Winkfield lived longer, freer and infinitely better overseas, but never changed his citizenship. Or his feelings. In his heart, the United States was always home.

Overlooked while living in the United States, Winkfield has been largely ignored since he died. Eighty jockeys are enshrined in the National Racing Museum’s Hall of Fame — Jimmy Winkfield is not among them.

He always loved America more than America loved him.

Tasting victory Derby wins in 1901, 1902 put Winkfield on the map

Back in 1902, few would have taken odds that Winkfield would be the only black jockey to win the Derby in the 20th century. After all, African-American riders had won 15 of the first 28 Derbys.

In 1901, his third year in the saddle, Winkfield won 161 races and captured his first Kentucky Derby in a facile romp aboard His Eminence.

”I got him away in front and stayed there,” Winkfield told Sports Illustrated in 1961. ”Was nothin’ to it.”

That wasn’t the case in 1902. Winkfield rode Alan-a-Dale, whose skinny legs were so tender that the
Derby was his only start as a 3-year-old. He trained for the race by pulling a sulky, like a harness racer. His trainer was afraid that even a jockey’s weight would overstress the colt’s brittle bones. In the Derby, he would go lame two strides past the finish line and wouldn’t race again for a year.

When fit and sound, Alan-a-Dale was ”a rapid good horse,” Winkfield said, but his stablemate The Rival was held in higher regard. Owner Thomas Clay McDowell, great-grandson of Kentucky statesman Henry Clay, was determined to see one of them win the Derby. He recruited a white jockey, East Coast hotshot Nash Turner, to Churchill Downs for the big race.

Printed in Volume 1 Issue 8