Jimmy Winkfield aboard Alan-a-Dale in the 1902 Derby | Courtesy of Larry Muhammad
Jimmy Winkfield aboard Alan-a-Dale in the 1902 Derby | Courtesy of Larry Muhammad

Just in time for Derby, retired journalist and playwright Larry Muhammad presents his 2010 play “Jockey Jim,” which depicts the harrowing story of Jimmy Winkfield, a black jockey who rose to fame in the early 1900s and won two Derby races — but who later had to endure overt racism from both job and country. The play runs each night of Derby week, starting Saturday, April 30, and continuing through Friday, May 6, at the Henry Clay Theater.

Muhammad tells Insider he was first drawn to Winkfield’s story after he read the book “The Great Black Jockeys” by Edward Hotaling. Although rare today, African-American jockeys dominated the early years of the Derby, winning 15 of the first 28, including the inaugural run on May 17, 1875.

Jimmy Winkfield
Jimmy Winkfield

Winkfield was one of the first superstar jockeys and rode in races all over the world. He won the Derby in 1901 and ’02, and then went to Russia for more fame and fortune. However, upon returning to the United States after World War II, he found a country steeped in racism and a horse-racing industry that no longer wanted him.

“It’s arguably the most fascinating saga in racing history, and it’s set against a backdrop of 20th century bigotry, war and upheaval,” says Muhammad. “A poor boy wins the Kentucky Derby — twice, then rides winners from Moscow to Warsaw to Paris at a time when black jockeys were becoming extinct in America, marries an heiress, survives the Russian revolution and World War II in Europe, and returns to the U.S. to overcome racism and reclaim a forgotten legacy.”

He explains that black jockeys stopped being used at tracks across the country because of bigotry and professional jealousy. Dominant black horsemen were originally slaves, and then sons of slaves, so when they competed on tracks in the North, white jockeys would literally attack them during races, ramming them and their horses into the rails.

“Racing officials turned a blind eye, and owners, rather than hire black riders and risk losing a race and hurting a prized thoroughbred, just began hiring only white riders,” says Muhammad. “That’s partly how Winkfield ended up in Europe.”

In his prime in the early 1900s, Winkfield earned more than $100,000, and it was reported he spent time with the likes of Josephine Baker, Bing Crosby and Paul Robeson. But when Nazi occupation forced him and his wife to leave Paris and return to America, he struggled to survive in a racially segregated country where black jockeys had been forgotten. Winkfield and his wife also faced hardship due to the fact that they were an interracial couple, which was illegal at the time in most states.

Bing Crosby and Jimmy Winkfield | Courtesy of Larry Muhammad
Bing Crosby and Jimmy Winkfield | Courtesy of Larry Muhammad

Muhammad believes Winkfield’s story is an important one to remember this time of year. It not only speaks to the themes of courage and perseverance, but also “that the Kentucky Derby and thoroughbred racing in the U.S. has a rich African-American heritage,” he says.

“Jockey Jim” runs April 30-May 6 at 8 p.m. at the Henry Clay Theater, 604 S. Third St. Admission is $20 at the door, and for reservations, email [email protected].

Sara Havens
Sara Havens is the Culture Editor at Insider Louisville, known around town as the Bar Belle (barbelleblog.com). She's a former editor of LEO Weekly and has written for Playboy and The Alcohol Professor. Havens is the author of two books: "The Bar Belle" and "The Bar Belle Vol. 2."