THE FIRST KENTUCKY DERBY is celebrated in this 1875 collage. The winning team of owner H. Price McGrath, jockey Oliver Lewis and thoroughbred Aristides are pictured in what is known to be the only verified photo of Lewis. (Photo courtesy of Keeneland Library Collection, all rights reserved).
OLD HILLSIDE DISTILLERY made a commemorative bottle last year celebrating Oliver Lewis’ achievement as the first jockey to win the Kentucky Derby in 1875. (Photo by Bill Caine)
Long before the pageantry and week-long festival on the first Saturday in May, three young black men from Woodford County made their mark on horse racing history.
Oliver Lewis, William “Billy” Walker and Erskine Henderson were all born in Woodford County and etched their names on the list of Kentucky Derby winners. Their wins are reminders that skill – not color – is the determining factor on the race track. The right horse with the right trainer and jockey are unstoppable forces.
Winning the Derby at 19
Born on Dec. 22, 1856 in Woodford County to Goodson and Elanora Lewis, who relocated to Lexington in the 1870s, Oliver Lewis spent his time working with horses and found a love for the sport of horse racing. Ansel Williamson, an African American Hall of Famer, trained Lewis as a jockey and horseman.
Lewis was the winning jockey in the inaugural Kentucky Derby on May 17, 1875 when he was 19 years old. He held Aristides steady with a late surge, winning the Derby in two minutes and 37 ¾ seconds, which was an American record.
Initially, the consensus was that Aristides would be a pace horse for the favorite Chesapeake, but Lewis and his horse had other plans.
Despite the enormous success of winning the Derby and a second-place finish in the Belmont Stakes, Lewis did not continue his riding career and went on to become a successful bookmaker (A legal profession at the time) and helped lay the groundwork for traditional handicapping and the Daily Racing Form.
Lewis married Lucy Wright in 1881, and the couple had six children. They moved to Cincinnati in the 1900s, where Lewis worked for the City Street Department until he died in 1924.
Lewis is buried in Lexington at the African American No. 2 cemetery. Oddly enough, his Derby win was not mentioned in his obituary.
For many years Lewis’s birthplace was debated, but confirmation from the Keeneland Library places birthplace in Woodford County.
A life in horse racing
William “Billy” Walker was born in 1860 and a professional jockey when he was a teenager. Working under the guidance of horseman Daniel Swigert, Walker built a reputation as a patient jockey who knew when to push a horse.
At just 17 years old in 1877, Walker rode Baden-Baden to victory in the Derby, making him one of the youngest ever to win the Run for the Roses. Walker’s patience paid off as he rode Baden-Baden to a come-from-behind win, shocking the field and claiming the $3,300 purse.
As a breeder, trainer and pedigree expert, Walker continued a life in the horse business. Later in life, he worked as a clocker at Churchill Downs and gave analysis to trainers and owners alike. During Walker’s long career, he worked with E. Madden, the operator of Hamburg Place. Together, they molded decades of American Thoroughbreds.
In racing circles, Walker was respected as a man who could recall bloodlines instantly and had a sixth sense for race-day form.
Although he gave his life to the sport of horse racing, Walker was buried in an unmarked grave in a Louisville Cemetery until nearly 100 years after his Derby win, when a headstone was finally placed to honor his accomplishments in 1996.
A Derby win after being born in slavery
Erskine Henderson, aka “Babe,” was atop Joe Cotton as he ran to victory in the 11th running of the Derby May 14, 1885.
Born into slavery in Woodford County, Henderson developed into a horseman as a boy, which prepared him for the biggest stage in horse racing.
Erskine began his horse racing career at age 14 and gained early recognition for his feathery frame, weighing only 80 to 110 pounds. His riding skills were exceptional and earned him the position of a jockey with S. J. Salyers’ stable, marking the start of his ascent in the Kentucky racing circuit.
Henderson and Joe Cottom won a trio of derbies, including the Coney Island Derby and the Tennessee Derby that year.
In 2024, during the 150th celebration of the Kentucky Derby, Louisville Tourism also requested 11 extravagant horse statues created in honor of Black Derby jockeys who historically won the race. During those celebrations, Henderson received a statue from artist Keith Anderson to honor his legacy as one of the Derby victors.
Discrimination and racism
Competitors like Lewis, Walker and Henderson were eventually removed from the industry because of discrimination and racism, but their contributions will always hold importance.
In the early days of the Kentucky Derby, the presence of Black achievement stood out. By the turn of the 20th century, racism made it impossible for Black jockeys to continue being a part of a sport they helped create. After 1921, there were only two Black riders, and no Black jockeys have won since 1902.
Now, thanks to local researchers, descendants, and civic societies dedicated to preserving black history, these riders’ names are being returned to the public. Woodford County’s part in horse racing history is now being written alongside the tale of the Black sportsmen who dominated present-day Churchill Downs.
Their legacy continues not only in the history books but also in the increasing acknowledgment that the initial champions of the Kentucky Derby were black horse riders from Woodford County, a small Kentucky county that nurtured legends of the horse racing history.
Many thanks to the Woodford County Historical Society and the Keeneland Library staff for the information in this story.