On May 17, 1875, Oliver Lewis won the very first running of the Kentucky Derby while riding Aristedes with a time of 2:37.75, setting an American record. He claimed his victory by two lengths. He also rode the colt to a win at Belmont Stakes and won a total of three races at what would become Churchill Downs in Louisville, Ky.

Later after retiring from racing horses, he still remained involved in the business and enjoyed success as a horse handicapper and a bookie. Little is known about his life outside of racing, but he was notably left out of literature about the sport for more than a century. He died in 1924 and was inducted into the National Museum of Racing and Hall of Fame in 1998.

When he was just 12 years old, Alonzo “Lonnie” Clayton joined his brother Albertus, who was already a jockey in Chicago and began his amazing career in racing. In 1890, at just 14, he turned professional and the next year he won the Champaign Stakes at Morris Racetrack Park in New York riding Azra, a horse that proved crucial to his future. In 1892, Clayton and Azra raced to the Winner’s Circle at the Kentucky Derby. At 15, he was its youngest winner ever.

Clayton became one of the most prolific racers of those times, winning 144 races in 1895 alone, and later winning the Preakness Stakes. Although he enjoyed good fortune from his racing days, racism forced him and many other Black jockeys from the sport, costing him his wealth. He died in 1917 in California. He was inducted into the Arkansas Sports Hall of Fame in 2012.

Coming from a family familiar with horses, James “Soup” Perkins' father was a hostler, a caretaker of horses owned by travelers, and his brothers were both jockeys and trainers. He followed them into horse racing and even would prefer eating soup for meals to remain light weighted, hence his nickname.

Starting at just 13 years old, Perkins won five of the six appearances he made in his debut at the Kentucky Association Race Track and placed second in the sixth. In 1895, riding Halma, he became the second youngest jockey to win the Kentucky Derby, winning by five lengths. He rode the same steed to victory later at the Phoenix Stakes. In 1899, unable to keep a low enough weight for the sport, he switched to horse training. He died in Canada in 1911.

If there’s a G.O.A.T. of American jockeys, Isaac Burns Murphy may be that person. He consistently won at least a third of his mounts each year and by his counts, he won 44 percent of them, although the number could not be verified in records. He was a three-time Kentucky Derby winner, a five-time Latonia Derby winner, and four of the American Derby’s first five runnings. 

Not only was he known as a winner, but Murphy was a man of integrity. He was once offered a bribe to allow  a horse to loose the 1879 Kenner Stakes, but would not accept the money. He died in 1896 and was inducted into the National Museum of Racing and Hall of Fame  in 1955, becoming the first Black jockey to receive the honor.

Boasting more than 1,100 wins, Willie Simms built himself up from learning to ride horses in a livery stable near his birthplace of Augusta, Ga. His equestrian skills gained the notice of wealthy horse owners who entered him in races along the East Coast. In 1893, his horse Dobbin finished in a dead-heat with the previously undefeated Domino, which captured national attention.

In 1898, Simms became the only Black jockey to win all of the Triple Crown classic races, claiming victory at the Kentucky Derby (which he won twice), the Belmont Stakes and the Preakness Stakes. He also became the first jockey to win a race in England on an American horse. He died in 1927 and was inducted into the National Museum of Racing and Hall of Fame in 1977.

Born into slavery in 1860, by age 13, William "Billy" Walker had won his first race riding Astral during the Lexington, Ky., fall meet. Although he was in the first Kentucky Derby in 1875, he did not win. Instead, victory came for him in 1877 when he rode Baden-Baden for a two-length victory.

With multiple wins in major races around the country, Walker enjoyed a 25-year career, with his last race at Churchill Downs in 1896. He transitioned into being a specialist in breeding horses and became one of the nation’s leading pedigree experts. Walker died in 1933 and in 2006, the William Walker Stakes was named in his honor.

Jimmy Winkfield is recognized as one of the most gifted jockeys of his era, but his life story is even more amazing. Winkfield had become the second rider (behind Isaac Murphy) to win the Kentucky Derby back-to-back. He became a celebrated athlete, but his stardom came at a time when Black jockeys were being forced out of the sport due to racism. A clash with an owner left him blackballed and he wound up racing in Europe, again proving his prowess. But that also put him squarely in front of the Bolshevik Revolution in Russia, where he had been racing horses for Czar Nicholas II. He fled to France where he married and continued racing until his retirement.

But during World War II, he was forced to flee again, this time from the Nazis, returning to America. Cris-crossing the Atlantic several more times, between the U.S. and France, died there in 1974 at age 91. In 2004, Winkfield became the third Black jockey inducted into the National Museum of Racing and Hall of Fame. The New York Racing Association inaugurated the Jimmy Winkfield Stakes in 2005.