There are few things that are more intrinsically linked to the state of Kentucky than bourbon and the Derby. Although bourbon can be made anywhere in the U.S., the Bluegrass State is the spiritual home of this American whiskey category. In fact, about 95 percent of all bourbon is produced there (“The rest is counterfeit,” governor Andy Beshear once quipped). The Kentucky Derby, however, has always called Kentucky home, specifically Churchill Downs in Louisville where it has taken place since 1875, making it the longest running sporting event in the country. Kentucky is the equine center of the nation, with horse farms producing prize-winning thoroughbreds, trotters, and pacers for many decades; distilleries have been making bourbon in the state legally (and illegally) for centuries. So it seemed like an obvious move back in 1999 when the Derby named its first official bourbon. But given that it was a relatively new brand at the time, how did Woodford Reserve manage to achieve that distinction?

According to Woodford Reserve master distiller emeritus Chris Morris, the distillery wasn’t looking for a partnership with the Derby at the time. On the contrary, the Derby approached Woodford’s parent company, Brown-Forman (which also owns brands like Jack Daniel’s and Old Forester), about the opportunity. “Brown-Forman had been affiliated with Churchill Downs and the Derby through our premixed cocktail and mint julep program for 20 years,” he said. “So we obviously had a good relationship.”

The problem that both bourbon and the Derby faced was that they were just not very popular in the late ‘90s, something Morris attributes to a lack of interest from the younger generation. “Horse racing was pretty much in the same situation that bourbon was,” he said. “It had an old audience, and its properties, including Churchill Downs, were aging. Bourbon also had an old audience, and its facilities were being consolidated and shut down.”

The NTRA (National Thoroughbred Racing Association) decided that it needed to inject some youth and vigor into horse racing, and asked Woodford to be its partner. It’s worth noting that while there is a long history of making whiskey on the site of the Woodford distillery in Versailles, Kentucky, the brand was actually founded just three years before in 1996. So given the fact that there were plenty of other distilleries that had been around in some form or another for a century or more, why did this upstart bourbon get the nod?

“We were the exact kind of brand they needed because we were doing what they needed to do—introducing a new generation to bourbon, and a new generation to horse racing,” said Morris. Woodford Reserve was different from its competition at the turn of the century. It was not just a new bourbon, it was a new premium whiskey that came in an artfully designed glass bottle that looked like something you might want to actually display on your home bar. And the whiskey inside was very good, which of course played a role in the decision to form a partnership.

Master distillers and other industry insiders credit the quality of Kentucky’s water as being a crucial ingredient in making bourbon, and there’s some science behind that. The water is filtered through layers of limestone which removes iron, a mineral that can negatively affect the whiskey’s flavor. But according to master distiller Elizabeth McCall, who counts herself as a horse lover, Kentucky’s water is also crucial to its equine industry. She believes that there’s something poetic about the fact that Woodford is located so close to where future Derby horses are being bred. “Years ago, I remember visiting one of the horse farms, and they talked about how our water is a reason why the thoroughbred breeding industry is nestled right here,” she said. “The minerality makes it great for thoroughbreds to grow up drinking it, because it has calcium, potassium, and magnesium. And that’s the same reason why we love using it for distilling, (also because it filters out iron). So there are very practical reasons why our two industries are located here, and there can’t be a better bourbon that could tell that story than we can.”

From the start, Woodford has released an annual limited-edition Derby bottle, but this now highly collectible series has come a long way. The first few years featured a simple graphic on the label, and Morris admits that these were not very eyecatching. But starting in 2003, Woodford began working with specially selected artists to design Derby-themed labels for each release, a practice that continues to this day. “We try to make sure that they have a link to Kentucky so that there’s relevance to why they were chosen to do the Derby artwork,” said McCall. “It’s career-changing for the artist. I love that we’ve had artists who were at the very beginning of their career and just starting to get noticed, and now their careers have really taken off. It’s a huge honor to be a part of that.” Morris added that Woodford has only used one existing work of art on a Derby bottle label to date—LeRoy Neiman’s painting of Secretariat, which appeared on the 2008 edition.

Currently, the partnership between Woodford and Churchill Downs is set to run through 2027, but according to a rep for Brown-Forman it’s hard to see the brand not continuing to be involved with the Derby beyond that. And given the current state of the American whiskey industry, and global spirits overall, the Woodford team believes that a partnership like this helps spread the word about the bourbon, attracts consumers, and has made the Kentucky Derby a bucket list destination for people around the globe. “When Saturday Night Live makes fun of our $1,000 Mint Julep charity, that’s big,” said Morris referring to a past episode of the show. “We got the Kentucky Derby on SNL. They wouldn’t have done that by themselves. That’s the power of this partnership.”