The journey from the first Kentucky Derby to the 150^th has included its share of influential names, men and women who have left their mark on the country’s most famous race. Starting with founder Meriwether Lewis Clark Jr., the racetrack has survived thanks to Col. Matt J. Winn, the general manager and promoter who built the race into an event; and William E. Applegate, businessman and bookmaker who influenced the business side of Churchill Downs.

Alongside Winn and Applegate, Charles F. Grainger invested in both the city and its signature sporting facility, spending decades building the Kentucky Derby and Churchill Downs into integral parts of both Louisville and the sport of horse racing.

Bluegrass Roots

Public Domain

Born in England, William H. Grainger was one of many in the early 19^th century who crossed the Atlantic to make his fortune in America. As a child, his family emigrated to New Jersey, where he was apprenticed to a brass finisher. As an adult, Grainger moved westward to Kentucky and put down roots in Louisville, starting the Phoenix Foundry and Machine Shop, which later became Grainger and Co. One of his 13 children, Charles, worked as a molder for his father before venturing into other trades, as a stonemason and a grocery clerk, eventually returning to Louisville to become a part of the family company.

The Grainger family not only invested in Louisville as employers but also as public servants. William served on the Louisville city council, representing the area in the state’s General Assembly, and then was elected a state senator. Charles followed in his footsteps, serving on the city’s Board of Alderman and sitting on the board of public works. In 1901, Grainger parlayed his experience in city government into a four-year team as mayor of Louisville, where he improved the city’s park system and invested in its public libraries, and then served as president of the Louisville Water Co., continuing his work improving the city’s public waterworks.

Charles F. Grainger’s years of service to his city coincided with his decades of contributions to another Bluegrass industry, the sport of horse racing.

One Man’s Work

Like many men of his era, Grainger’s success in business enabled him to pursue other interests, including those of the sporting kind. As a native Kentuckian, he invested in the state’s signature sport as an owner, but his role as a public servant also gave him opportunities to support horse racing in other ways. Grainger would become one of the earliest members of the Kentucky Racing Commission. Then, after his term as mayor, the Louisville native would take on his most important role: president of the New Louisville Jockey Club.

In 1894, bookmaker and bourbon distiller William E. Applegate was among the group of investors that created the New Louisville Jockey Club, taking over a flailing Louisville Jockey Club and its racetrack, now known as Churchill Downs, from founder Meriwether Lewis Clark Jr.

Click image to purchase shirt.

A decade later, Grainger, Applegate, and a handful of others, including Matt J. Winn, purchased the racetrack outright, rescuing it from a potential takeover by another business interest and setting the stage for its signature race’s development into a national event.

Bookmakers had been the primary means for gambling on the Kentucky Derby since its earliest days, though the track also offered auction pools and pari-mutuel wagering that first year. Bookmaking and auction pools survived while Clark’s pari-mutuel machines went into storage, as most patrons were not educated on how that form of gambling worked. The anti-gambling movement of the early 20^th century put the sport in jeopardy as laws like Hart-Agnew in New York forced racetracks across the country to close. When James Grinstead succeeded Grainger as mayor, he persuaded the city council to ban bookmakers ahead of the 1908 Kentucky Derby. This left the track’s leadership, including Winn and Grainger, scrambling for solutions.

The answer came in the form of a loophole that allowed pari-mutuel wagering in Louisville. The Louisville Jockey Club leadership quickly assembled as many betting machines as they could ahead of that year’s Derby and succeeded in acquiring six, enough to allow racing to go forward. Grainger’s iron and steel company then went to work producing pari-mutuel machines for racetracks across North America. Additionally, Winn’s and Grainger’s efforts also made this kind of wagering more sustainable for the sport as a whole as bookmakers, the target of many reformers’ ire, fell out of fashion in favor of the more equitable pari-mutuels.

Grainger not only helped save the Derby and its home through his influence and industry, but also left other positive impacts on racing in his native city.

A Lasting Legacy

During the former mayor’s tenure as president of the Louisville Jockey Club, he partnered with Matt Winn to help raise the Derby’s profile nationally. The purse for the 1905 edition was only $4,850; by 1923, when Grainger passed away, the purse had increased to $53,600. With winners like Regret, Sir Barton, and Zev, the Kentucky Derby had gone from a paltry field of three during that first year to upward of 20 horses in the early 1920s.

Additionally, Grainger used his own money to establish a school for jockeys, exercise riders, and stable boys at the racetrack. He hired the teachers and provided a cottage for the young men to attend classes in between their duties, ensuring that they would continue to receive a proper education. He even provided a prize for the student who showed the most improvement each year.

A century after his passing, Charles F. Grainger stands alongside Col. Matt Winn as one of those whose tireless work on behalf of the Kentucky Derby and Churchill Downs have made both enduring parts of the sport of horse racing in America. The vision of this businessman and his contemporaries turned Clark’s grand experiment into a bucket list event for sports fans around the Bluegrass and beyond.