A featured ingredient of the famed mint julep, bourbon is as synonymous with Kentucky as horses. Both are key components of the Bluegrass State’s economy. Bourbon is a $9 billion industry, and the state is home to 100 distilleries owned by 84 companies producing 95% of the global bourbon supply. This golden spirit is powering an industry that employs more than 23,000 people, opening up opportunities for underrepresented populations to make their own mark on this uniquely American phenomenon.

For the four men behind Old Hillside Bourbon Co., the spirit is more than just a business: it powers their mission to honor the contributions African Americans have made to the sport of horse racing. Their newest blend, The Trifecta, celebrates Sylvia Bishop, Eliza Carpenter, and Cheryl White, three African American women who broke through barriers and made a name for themselves in the sport of horse racing.

Four Friends and a Dream

Growing up in Durham, N.C., Jesse Carpenter and Brian Burton attended Hillside High School, one of the oldest historically Black high schools in the United States, going their separate ways after graduation and eventually catching up again as adults.

“How we got started was Jessie, one of our co-founders, had moved to Lexington after the military,” co-founder and CEO Emmanual Waters shared. “After his son went off to college, he was just in the house with his wife and his daughter and a bunch of girls. He said, ‘I’ve got to get out of the house.’ And so, he just started going to horse races to get away from the girls. And he just fell in love with bourbon and horse racing.”

Purple Heart Tribute (Courtesy of Old Hillside Bourbon)

Jesse and Brian reconnected over their love of both bourbon and racing, noting how underrepresented African Americans are in both despite their earlier connections to the crafts of distilling and riding. As the COVID-19 pandemic sent the country into lockdown, Jesse and Brian started dreaming of creating their own bourbon company, and Old Hillside was born. To complement Jesse’s business background and Brian’s IT skills the pair recruited childhood friend Courtney Tucker, who added his marketing and communications experience to the venture; then Courtney enlisted his cousin Emmanuel Waters, a contracts consultant, and a new quartet of distillers was born.

Inspired by the stories of the Black jockeys that dominated racing in the late 19^th century, the four set out to create a bourbon brand that honored the legacies of riders like Oliver Lewis, Isaac Murphy, and James “Soup” Perkins. “When I got on a call and Jesse told me about these jockeys, I was just blown away, and honestly I was embarrassed that I didn’t know this history,” Waters remembered. “Why isn’t anybody talking about these Black jockeys? So that was really the inspiration for the brand.”

The first Old Hillside offering, their Single Barrel Bourbon, debuted in September 2021. Five years later, the four friends have made Old Hillside into a spirited juggernaut, with five bourbons and rye whiskeys, each product’s label honoring African Americans, including Purple Heart recipients Staff Sgt. Derek Drew and Cpl. Nathan Jakubisin and famed jockeys like Murphy and Lewis.

Released in time for Women’s History Month, their newest spirit The Trifecta, a small batch blend from their Sparta, Ky., distillery, pays homage to three Black women and their impact on the sport they loved.

The Trifecta: Sylvia, Eliza, and Cheryl

“I found, I can't remember if it was an article or something, these three names. I saw Eliza Carpenter, but she was long gone since then. Then Cheryl [White] popped up as the first jockey,” Waters remembered. Soon, he added another name to the list: Sylvia Bishop, the first African American woman to hold a trainer’s license. The more he dug into these three names, the more he wanted to share their stories.

The Trifecta (Courtesy of Old Hillside Bourbon)

Each bottle of The Trifecta features a short biography of one of these three women: Bishop; Eliza Carpenter, a formerly enslaved woman who owned, trained, and even rode her own racehorses in the late 19^th and early 20^th centuries; and White, the daughter of trainer Raymond White, who became the first African American woman licensed to ride in the United States in the early 1970s.

Old Hillside worked with the Keeneland Library to find images of these pioneers and research their lives before sharing the proposed labels with each woman’s family. “It was very important for me, knowing what we were trying to do,” Waters shared. “I didn’t want them to think we were just taking their imagery and then slapping it on a label and just trying to make money off of them because that was never our intent.”

The quartet built relationships with both Bishop’s and White’s relatives, including Cheryl White’s brother Raymond, who co-authored a middle-grade book on her life with Sarah Maslin Nir, inviting them to be a part of their recent Los Angeles celebration of The Trifecta’s debut. There, the two families, who ironically knew of each other from their racing days in the 1940s onward, finally got to meet in person, an experience that moved Waters and his partners. “We literally created history and that was just something that was so iconic and amazing,” the Old Hillside CEO shared. “Their blessing meant everything to us. We’re just a conduit to tell their stories.”

Now for sale on the Old Hillside website, The Trifecta is just the latest opportunity for these racing fans and bourbon enthusiasts to share the history of African Americans in the country’s oldest sport. In the short five years that these four friends have been in the business, their success has them dreaming of what’s next as they continue to connect their community with its history.

On the Horizon

For Waters, his goal is to make names like Isaac Murphy and Cheryl White as familiar as Michael Jordan and Tiger Woods, and putting their stories front and center is part of their plan to do just that. “There’s a million bottles [of bourbon] on shelves, but you’ll find our label actually stands out. We designed it that way,” he said. “Every bottle actually shares a biography. Nobody else is doing that.”

Their vision has translated to sales. At a bottle signing in their hometown of Durham, “people were buying 6-12 bottles at a time. In 20 minutes, we had to stop and say, ‘Hey, you can only buy two bottles.’ It was literally that crazy,” Waters remembered. “I was like, ‘Wow, this is something. We have something here.’ ”

For this most recent release, they produced 600 bottles of The Trifecta and have sold 80% within weeks, that connection to Bishop, Carpenter, and White resonating with bourbon drinkers everywhere.

“Every bottle we do tells a story,” he reflected. “we’re going to keep that mantra as long as we can. I don’t want to just put something generic out.”

As they look toward the future, the men behind Old Hillside are planning a tasting room in Durham, searching for a producer for a potential documentary or film, and developing more bottles honoring other African Americans in the sport of horse racing. This Women’s History Month, they also cherish the chance to reacquaint us with Bishop, Carpenter, and White, three African American women who did not let societal barriers keep them from thriving in the sport.

“Women are the backbone of America,” Waters observed. “All these women, all their stores are, to me, a story of triumph. What we’re doing and the stories we’re telling are so meaningful. They’re bigger than us.”