Everything You Always Wanted To Know About Pappy Van Winkle

"What’s in a name? In the case of Pappy Van Winkle, everything. As any bourbon nerd will tell you, when the Van Winkle name is on a bottle of whiskey, the price tag skyrockets into the thousands; MSRP be damned. But unlike other old-timey whiskey monikers created in an advertising agency lab, Julian Prentice Van Winkle Sr. was a real person who founded the company his descendants run to this day.

Meet Pappy Van Winkle

Long before his visage graced the label of Pappy Van Winkle's Family Reserve, Julian Van Winkle was born in Danville, Kentucky, in 1874. The Van Winkles trace their American lineage back to New York City’s earliest Dutch settlers. In the late 18th century, the family migrated west. Julian grew up amidst affluence and tradition. His father, John Van Winkle, was a prominent local lawyer who briefly served as Kentucky’s Secretary of State.

Rather than follow his father into the legal profession, Julian struck out on his own. In 1893, not yet 20 years old, he took a job with another whiskey pioneer, William Larue Weller, who helped develop the wheated mash bill that's still used today to distill Van Winkle and Weller bourbons. Working for W.L. Weller & Sons liquor distributors, Julian began traveling through the South and Midwest as a salesman.

The Golden Years of Pappy Van Winkle

In 1909, some years after Weller's passing, his sons sold the business to Van Winkle and Alex F. Farnsley. The duo frequently sourced liquor from the Stitzel Brothers Distillery in Louisville. Ultimately, they acquired an ownership stake, and renamed it the Stitzel-Weller Distillery. This became a hallowed name in the whiskey business, producing notable brands like Old Fitzgerald, Rebel Yell, Cabin Still, and Old Elk.

During Prohibition, the Stitzel-Weller Distillery ensured its survival by securing one of six licenses to produce whiskey for medicinal purposes. Soon after Prohibition was repealed, they began construction to expanded the distillery, and opened a new Stitzel-Weller Distillery in Shipley, Kentucky, on Derby Day in 1935. Coincidently, the opening coincided with the start of Omaha's historic quest for the Triple Crown, eventually becoming the third horse to achieve this prestigious achievement.

Now in his in sixties, Julian Sr. helmed a whiskey empire renowned for its commitment to quality. A plaque outside the distillery echoed his ethos: "We make fine bourbon. At a profit if we can. At a loss if we must. But always fine bourbon." Alongside his dedication to business, he nurtured familial bonds, bringing his son, Julian Jr., and son-in-law, King McClure, into the fold. Pappy remained actively involved in the business until his passing in 1965 at the age of 91.

The Stitzel-Weller Distillery Falls on Hard Times

Julian Proctor Van Winkle Jr. took on a leadership role at Stitzel-Weller just before his father’s death. With the popularity of bourbon on the decline, however, the family was forced to sell the business in 1972. While their brands were sold off, the distillery was rebranded as the Old Fitzgerald Distillery, which then closed in 1992. Following its purchase by international beverage conglomerate Diageo in 2014, it was reopened as a tourist attraction on the Kentucky Bourbon Trail called the Bulleit Frontier Whiskey Experience. Now operating once again as the Stitzel-Weller Distillery, it’s currently open for visitors and produces brands such as Blade and Bow, I.W. Harper, and Orphan Barrel.

Where Does the Name, 'Old Rip Van Winkle' Come From?

Julian Jr. retained rights to the brand Old Rip Van Winkle bourbon and, despite selling the distillery, continued to sell whiskey. The name honors the family whiskey legacy, but also draws inspiration from Washington Irving's colonial American folktale of the same name.

As the story goes, Rip Van Winkle was a Dutch settler who lived in upstate New York. After imbibing a potent liquor, he wanders into the woods to get away from his wife, and falls asleep for 20 years. When he wakes up, he discovers many things have changed. Most importantly, he's slept through the American Revolution.

From 1972 until he died in 1981, Julian Jr. continued to source whiskey from the Stitzel-Weller Distillery. These barrels of bourbon used the same wheated mash bill his father made famous. These historic bottles are now collector's items that fetch insane amounts of money at auction.

The Age Of Pappy

Julian Van Winkle III assumed leadership of the business following his father's passing in 1981. Despite the ongoing low demand for bourbon, he doubled-down on highly-aged barrels. In 1994, Pappy Van Winkle's Family Reserve made its debut, featuring the iconic photograph of his grandfather enjoying a cigar on its label. His 20-year-old bourbon was unprecedented. Most bourbons weren't age stated at the time, and were often bottled before reaching 10 years old.

In ensuing decades, Julian III added Pappy Van Winkle's Family Reserve 23 Year Old and 15 Year Old bourbon, Van Winkle Special Reserve, and Van Winkle Family Reserve rye to the brand's lineup. The reputation of Pappy Van Winkle continued to grow, in tandem with bourbon’s renewed popularity.

In 2002, with demand outpacing supply, the Old Rip Van Winkle Distillery entered into an arrangement with Buffalo Trace Distillery to produce their bourbons using “Pappy's exact recipe,” according to their website. In 2011, Pappy Van Winkle's reputation hit a crescendo when Anthony Bourdain posted on Twitter, "I am considering a full back Pappy Van Winkle tattoo."

As the fourth generation of Van Winkles step into the fold, with Preston Van Winkle joining the family business in 2001, the popularity of Pappy Van Winkle bourbon shows no signs of abating. Now known simply as "Pappy," the brand has transcended the world of whiskey. The bottles are the most sought-after American whiskey, and symbolize the value of tradition, and the history of Kentucky bourbon. Behind it all stands the legacy of Julian "Pappy" Van Winkle, whose unwavering devotion to quality bourbon is the backbone of a liquor empire.

Photographs courtesy of the Old Rip Van Winkle Distillery