Historical Jockey Profile: Jimmy Winkfield

The last in a series of great African-American jockeys who won the Kentucky Derby, Jimmy Winkfield went on to achieve fame and fortune across Europe in a career that reads like a gripping novel – or a tale best told by cinema.

Winkfield was the 17th, and final, child born to a sharecropping family in Chilesburg, Kentucky, in 1880. After his parents died, young “Wink” took up residence with a sister in Lexington, where he worked as a carriage driver before landing a job on the racetrack.

Once hired by Bub May, Winkfield progressed from stable hand/exercise rider to jockey. 

“May brought him up, but May never had to teach that boy how to ride,” observed Col. Phil Chinn, a fixture of the Bluegrass establishment. 

“He was a natural from the start. He had no particular style; he just sat up there like a piece of gold.” 

By the age of 20, Winkfield secured his first Kentucky Derby mount aboard Thrive, who rallied for third to front-running favorite Lieut. Gibson in the 1900 edition. 

Winkfield won the next two runnings of the Kentucky Derby in 1901-02, becoming just the second rider to score back-to-back wins. The first was the iconic African-American jockey, Isaac Murphy. Their feat was not equaled until Ron Turcotte rode Riva Ridge (1972) and Secretariat (1973). The only others to achieve it are fellow Hall of Famers Eddie Delahoussaye (Gato Del Sol and Sunny’s Halo in 1982-83), Calvin Borel (Mine That Bird and Super Saver in 2009-10), and Victor Espinoza (California Chrome and American Pharoah 2014-15). 

Both of Winkfield’s Derby victories came in wire-to-wire fashion, but His Eminence (1901) was a steering job compared to the prolonged suspense aboard Alan-a-Dale (1902). In one of his finest pieces of artistry in the saddle, Wink nursed the unsound Alan-a-Dale along, floated his oncoming rivals onto the deepest part of the track, and held on by a nose. 

Winkfield arguably should have taken a third straight Derby in 1903. A rare misjudgment of timing –moving too soon on the odds-on favorite ironically named Early – left him vulnerable to late-running Judge Himes, and he wound up second.

Considering that Winkfield compiled a remarkable Derby record of two wins, a second, and a third, from four starts, he likely could have added more. But a remorseless combination of personal and societal factors drove him to leave the country.

Winkfield broke a verbal agreement to ride a horse for prominent owner/trainer John Madden in the 1903 Futurity, and instead picked up a mount on a rival. Madden gained revenge by getting Winkfield virtually ostracized, and the once in-demand jockey found himself devoid of opportunities.

By that point, American racing was already feeling the strain of an economic downturn and the political threat posed by the antigambling movement. If even leading white jockeys were decamping for more lucrative offers in Europe, the situation was worse for African-American jockeys who had to deal with systemic barriers of segregation as well as deliberate campaigns of racist intimidation.

America’s loss would be Europe’s gain as Winkfield joined the exodus. By 1904, he was the contract rider for Armenian oil tycoon Mikhail Lazareff in Russia and its Polish territory. 

An immediate hit, Winkfield was soon landing major races from Warsaw to Moscow and St Petersburg, and ranked as Russia’s champion jockey from 1906-08. He was feted as the “black maestro” and “black miracle-worker” by the racing public that loved to bet on him.

Winkfield then signed on with a Polish prince, Stanislaw Lubomirski, and became a celebrity in the aristocratic racing circles of the Habsburgs’ Austro-Hungarian Empire and the Kaiser’s Germany as well as Tsarist Russia. That dynastic world, however, was in its waning days, soon to be destroyed by World War I and revolution. 

As a wealthy expat associated with the ruling class, Winkfield fled Moscow when the Bolsheviks seized power in 1917. He found a brief refuge in the Black Sea resort of Odessa, but the racing community there evacuated en masse rather than fall into the hands of Lenin.

In an epic venture, Winkfield and other dedicated horsemen guided more than 250 Thoroughbreds on a long march to safety in Poland. The bedraggled column finally arrived at Warsaw after a circuitous, and often perilous, three-month trek in 1919. 

Winkfield resurrected his riding career in Paris, thanks to the good offices of another Armenian oil tycoon, Leon Mantacheff, who had employed him on the eve of the Great War. Once again, his skills translated borders, and Wink captured such prizes as the Grand Prix de Deauville (1922) and Prix du President de la Republique (1923).

Gradually transitioning into a trainer at his home in Maisons-Laffitte, Winkfield retired from riding by 1930 with approximately 2,300 wins in a career spanning two continents. But his hard-won status would be swept away in another conflagration.

As World War II raged in 1940, the French authorities commandeered Winkfield’s property, and then the invading Nazis seized it. The 60-year-old Winkfield, undaunted, raised a pitchfork to defend a horse being abused by a Wehrmacht soldier. 

Winkfield had to flee again, this time making his way to New York in 1941. Having lost everything, he was reduced to operating a jackhammer as part of a WPA project before latching onto the Bostwick stable in Aiken, South Carolina. He eventually set up shop as a trainer, and gave a few rides to a promising young man by the name of Bill Hartack, a future Hall of Famer and five-time Derby winner.

Returning to live in France in 1953, Winkfield made one final visit to the Kentucky Derby in 1961. But the pervasive racism was on display as he was initially denied entrance to a dinner at the Brown Hotel, despite the fact he was an invited guest. All the attendees ignored him too, except for one – retired jockey Roscoe Goose, best known for his 91-1 upset aboard Doneraile in the 1913 Derby. Goose sat at his table and treated Wink as an esteemed colleague. 

Winkfield’s reception in Louisville was in stark contrast to his status in Europe, where he was welcomed by grandees. His accomplishments were recognized belatedly in his American homeland. 

Thirty years after his death at Maisons-Laffitte in 1974, he was enshrined in the National Museum of Racing’s Hall of Fame. Aqueduct renamed a stakes race in his honor in 2005, and that spring, the U.S. House of Representatives passed a resolution that  

“(1) celebrates the remarkable life and accomplishments of one of the truly great American athletes, Jimmy ‘Wink’ Winkfield, who continuously overcame racism and other significant obstacles during his lifetime; and 

“(2) recognizes and celebrates the significant contributions and excellence of African American jockeys and trainers in the sport of horse racing and in the history of the Kentucky Derby.”

Yet all the posthumous tributes can’t quite capture Wink’s star quality in the halcyon days. 

“For us Russian horsemen in the days before the revolution, the name Winkfield was like Shoemaker, Arcaro and Longden – combined into one.”