Jimmy Winkfield

Jimmy Winkfield: The last of an era

The last Black jockey to win the Kentucky Derby became an international star due to American racism

By Tony McClean,

Black Athlete Sports Network

NEW HAVEN, Ct. (BASN) — Today, we take a look back at one of greatest African-American jockeys with the story of Jimmy Winkfield. Born on April 12, 1882 in Chilesburg, Kentucky, Winkfield began his racing career in 1898.

He went from being the youngest of 17 in a family of sharecroppers, to racing for $8 a month and eventually, $1,000 a race.

His racing stats show him winning back-to-back Kentucky Derbys (1901 on His Eminence, and 1902 on Alan-A-Dale). He was also the last Black jockey to win a Kentucky Derby.

After being blacklisted for breaking a contract with one horse owner, Winkfield accepted an offer to race in Russia, where he became a big star again. But as the Bolsheviks and the Communists rose to power in 1917, the sport suffered from its association to wealthy and aristocratic owners.

Winkfield led some 200 jockeys, trainers and owners to Poland. Many of the people involved in the move survived only by eating their horses along the way. Before leaving Russia, he won the Emperor’s Purse, the Moscow Derby twice and the Russian Derby three times.

In Germany, Winkfield won the Grand Prix de Baden. In Poland, he won the Poland Derby twice and in France, he won the Prix du President de la Republique. Winkfield would also train a horse that won the Grand Prix de Paris.

After his first two Kentucky Derby wins, Winkfield would lose his third Derby attempt. The sport of racing began to decline in the public eye due to anti-gambling movements and financial hard times.

To no surprise, some white jockeys resented the choice mounts and big money earned by successful Black riders. Races became combative including several riots between Black and White jockeys in Chicago.

Winkfield eventually tallied over 2,600 racing victories before retiring in 1930 and becoming a horse trainer. During World War II, he returned to South Carolina and worked at an Aiken horse farm, but went back to France in 1953 and lived there till he reached the age of 93.

In 1961, some 60 years after he first rode to Derby victory, Winkfield returned to Louisville for the race and still found recognition and respect elusive. Though he had been invited to a pre-Derby dinner at Louisville’s Brown Hotel, it was still segregated.

The doorman wouldn’t allow Winkfield and his family inside. They were eventually given some seats near the back of the hall, but nothing as far as recognition of his presence was done.

Jimmy Winkfield died on March 23, 1974 in Maisons-Laffitte, France.

Winkfield’s supporters were pushing for his admission to the Thoroughbred Hall of Fame, so he can join two other African-American jockeys (Isaac Murphy, Willie Simms) already honored there.

Finally on August 9, 2004, Winkfield was inducted into the National Museum of Racing and Hall of Fame. His daughter Liliane Winkfield Casey received the award from historian Edward Hotaling in Saratoga, New York.