Reclaiming the Derby from a history of profit and prejudice

A woman with a beat face, a hot pink organza hat and a tattoo of what looks like a Siberian husky on her left shoulder gazes from the pages of “At the Derby: Kentucky’s Grandest Celebration of Fashion,” (Rizzoli, $45).

In mid-April, the new book by equine lover and photographer Lili Kobielski landed in my mailbox, offering a vision of the Derby that did not match the one in my head.

Lili Kobielski is a contributing fashion photographer at Vogue who has photographed the Kentucky Derby for over a decade. "At the Derby: Kentucky's Grandest Celebration of Fashion" offers a view of Derby fashion and a deeper sense of the culture and history. (Courtesy of Lili Kobielski)

The Kentucky Derby is uniquely American, and its 151-year evolution from 1875 to the present is a master class in American culture. Kobielski’s images offered insight into what makes this “grand slice” of Americana both tradition and tragedy. The photos are visually arresting, but the deeper story is one of exclusion and rediscovery.

We may think that hiding the thornier parts of American history helps us move forward, but the harm always lurks under the surface.

I learned how to bet on horses in the summer of 1992. I would pick up my great-uncle in my metallic-blue, Isuzu-engineered Chevy and we would grab lunch at his favorite diner. Then we would drive to an industrial community on the far South Side of Chicago where Hawthorne Race Course, the oldest venue for horse racing in Illinois founded in 1891, operated off-track betting.

I always placed the easiest wagers, and once, when I won a few bucks, I promised I would pay for our next outing. This is the closest I have ever come to a racetrack, and I would not figure until much later why my great-uncle was so enamored with “the sport of kings.”

My grandfather, his brother, was born in 1892. He was old enough to be an impressionable young boy at a time when Black jockeys were still dominating the sport.

I never met my grandfather. He died tragically decades before I was born, but I like to think that my great-uncle picked up a passion for horse racing from his older sibling.

In the first 28 years of the Kentucky Derby, the most quintessentially American event in horse racing, 15 of the winning jockeys were Black. The crowd at Churchill Downs in Louisville, Kentucky, reflected the pride Black people felt at seeing jockeys who looked like them on the track.

"At the Derby: Kentucky's Grandest Celebration of Fashion" offers a view of the Derby fashion and a deeper sense of Derby culture and history. (Courtesy of Lili Kobielski)

But there was big money in horse racing, and the success of Black jockeys had a dark side. After successive wins in 1890 and 1891, Isaac Murphy became the highest-paid jockey in the country. He was a millionaire and a superstar. Talent and skill earned fame and fortune, but it also made him, and every other Black jockey, a target.

Historical records offer a host of reasons for the early financial and operational struggles of Churchill Downs, but until recently, those narratives did not call out the undergirding of avarice and racism.

For track owners, horse breeders and buyers, the Derby was a place to shamelessly display their wealth and influence. For jockeys, it was the place to earn those resources.

Betting was a chaotic enterprise in America, but as it became the primary source of revenue for horse racing — surpassing ticket and concession sales — bookmakers, track owners and white jockeys wanted to secure the bag. Locking Black jockeys out of the industry was part of the strategy.

On the track, white riders would hit Black riders with riding crops, box them out or run them into the rails. Off the track, the professional organization refused to license Black riders.

News articles arguing the superiority of white riders fomented public hostility toward Black jockeys, even as they continued winning races. For horse owners, hiring Black jockeys, no matter how talented, became a liability.

Photographer Lili Kobielski captures the famed two-spired grandstand and the action at Churchill Downs in this photo from "At the Derby: Kentucky's Grandest Celebration of Fashion." (Courtesy of Lili Kobielski)

Meriwether Lewis Clark Jr., the grandson of explorer Gen. William Clark of the Lewis and Clark Expedition, founded Churchill Downs and the Kentucky Derby, and he envisioned the Derby as a high-society spectacle for horse racing in the U.S. But the track was losing money, and some sources have suggested this is what led to his suicide in 1899.

By 1902, the Derby had new owners. That was the same year Jimmy Winkfield became the last Black jockey to win a Kentucky Derby.

By the time my great-uncle was born in 1904, the era of the Black jockey was waning. Between 1921 and 2000, there were no Black jockeys at all in the Kentucky Derby. Thirty years of history was undone by 100 years of exclusion, a harm that led Black Americans to believe the Derby was not a place for them.

Black fans still ventured to Churchill Downs to see the races, enduring the indignities of Jim Crow segregation, but some Louisville residents opted to host Derby parties in their homes, backyards and neighborhood streets.

"At the Derby: Kentucky's Grandest Celebration of Fashion" offers a view of the Derby fashion and a deeper sense of the culture and history. (Courtesy of Lili Kobielski)

That trend has continued in Louisville and other cities including Atlanta, where Alpha Derby Weekend, a three-day celebration, features golf, brunch, a best hat contest and a Derby watch party. The Derby-inspired fun has been a local tradition for more than a decade.

I never got the chance to use my prize winnings to treat my great-uncle to lunch and another trip to off-track betting. We planned a gathering, but I called to postpone. A few weeks later, he died unexpectedly.

Betting on horses helped end the reign of Black jockeys at the Kentucky Derby, but for me, through my great-uncle, it created an opening.

The photos in Kobielski’s book reminded me how important it is to lay claim to shared American history and invited me into a space that is part of my story too.