Just as sneakerheads go to the end of the earth for a pair of Air Yeezys and beer nerds hunt down white whales like Alchemist Heady Topper, fans of Kentucky whiskey tend to have one holy grail that haunts them: a bottle of Pappy Van Winkle bourbon.
Tracking down the brown spirit has become a popular sport in recent years—there’s even a Pappy Tracker that is solely dedicated to helping find the bottle nearest to you—with the 23-year-old Family Reserve acting grand-prize trophy (though many experts prefer the 15-year-old version for overall flavor). And like any product with this much hype, Pappy has spawned a crazy secondary market that’s responsible for Hollywood-worthy whiskey heists and eBay prices of up to $5,000 a bottle.
So what’s the story behind this liquid gold? Based in Frankfort, KY, the Old Rip Van Winkle Distillery is not actually a distillery at all, but rather a company that contracts the production of its coveted spirits to Buffalo Trace. Julian “Pappy” Van Winkle, for whom the bourbon is named, started selling whiskey in 1893 as a salesman for W. L. Weller. He would eventually go on to become the president of the Stitzel-Weller Distillery, which produced many well-respected whiskeys through the 1960s. However, years after Pappy passed away, stockholders forced the sale of the distillery; to keep the family tradition alive, Julian Van Winkle III and his father started buying back barrels of their own bourbon and bottling it under the Old Rip Van Winkle label (some of which is still being sold today).
Fast-forward three decades and the bourbon is what many aficionados consider to be the finest whiskey on the planet. Thanks in part to high-profile fans ranging from Bill Cosby to Anthony Bourdain, the spirit has gained cult status, with die-hard fans driving across state lines and even threatening violence just to get a taste. “We have people with literally billions of dollars who can’t find a bottle,” says Van Winkle III in an interview with Louisville Magazine, “They could buy a private jet in cash. They’d have an easier time buying our company.”
Here, we delve into the tradition, lore, and insane reselling antics that have helped make Pappy Van Winkle one of the country’s most intensely sought-after spirits.