Derby Dibs: How Old Rip Van Winkle Became the World's Most Coveted Bourbon

Bourbon is more than a category of whiskey. A good bottle of bourbon captures the essence of a bygone era—flavors, aromas, and all. No shortage of salt-of-the-Earth Americans can enjoy a well-deserved dram, but few bourbons go beyond being just a beverage. To some, bourbon is a society. A clan. A secret club, gestures and all—like the freemasons of whiskey. The pinnacle of that guarded bourbon milieu is Old Rip Van Winkle.

But how did this niche bourbon break into the mainstream and take the whiskey world by storm?

After William Larue Weller died in 1909, Pappy and his partner acquired the A. Ph. Stitzel Distillery company. Thus the Van Winkle dynasty began.

Whiskey was Pappy's forte, but the distinction between bourbon and moonshine was blurry in those early days. Weller whiskeys were far from exquisite since the distillery wasn't an austere follower of the tenets of bourbon making. This changed when Pappy became the company's president and started championing the traditional bourbon craft. As he would say, "there’s no one purer than a reformed prostitute." Even the U.S. federal government deemed the distillery pure enough, under Pappy's headship, for one of the few medicinal whiskey licenses issued during prohibition.

Pappy Van Winkle advocated for the bourbon tradition with the same vigor he vehemently resisted science. He was so averse to cold empiricism that he erected a sign at the old distillery that read "No Chemists Allowed." Pappy was opposed to high-mindedness, emphasizing that quality wasn't quantified (to the dismay of critics) but rather meticulously constructed from the sum of its parts. Pappy didn't need special gadgets, fancy marketing, or a secret sauce to make his meritorious bourbon. Just the right ingredients and lots of time.

Why Old Rip Van Winkle is the best bourbon

The two main things that distinguished Pappy's whiskey were wheat and water. The natural water in Pappy's home state of Kentucky was a reason for the region's illustrious bourbon-making reputation. Kentucky's limestone aquifers filtered the natural groundwater and left it with an uncommon composition of minerals that lend to making whiskey. The other thing setting Pappy's product apart was his mash bill: All bourbons are made mostly of corn mixed with cereals like malted barley or rye, but Pappy used wheat as a secondary grain. The predominant use of wheat was what made Pappy's bourbon taste smoother than his competitors'.

By 1970, the obsession with whiskey had all but disappeared. Americans weren't buying bourbon anymore, opting for the likes of gin and vodka. But Pappy, pushing 90 years old, didn't falter. He was the oldest living whiskey distiller before he died at 91 in 1972, leaving the fate of the Stitzel-Weller distillery in the hands of its shareholders. The glory days of the Stitzel-Weller distillery, which, as the legend goes, opened on derby day in 1935, had reached their end in 1972.

After Pappy passed away, the shareholders voted to liquidate the company and hand Stitzel-Weller over to its new corporate overlords. All that was left to Pappy's son, Julian P. Van Winkle, Jr., was the Old Rip Van Winkle trademark. Van Winkle the younger didn't stand idly by as his namesake withered away. He capitalized on the opportunity to revive his family bourbon business—except he only managed to keep it on life support.

For a decade, Van Winke, Jr. went to extraordinary lengths to restore the brand his father had built. He bought as many of Pappy's barrels as he could from the old Stitzel-Weller distillery and even searched every nook and cranny of Kentucky for ones that were sold to other distilleries. He even dragged his son, Julian Van Winkle III, along for the ride. But, after nearly a decade of scantily getting by, Van Winkle Jr. succumbed to cancer and left the herculean task of carrying the Van Winkle torch to his son, Julian. As Julian continued to search for lost barrels of priceless Pappy's bourbon, he eventually got short on cash and got desperate enough to take loans from practically every bank in Kentucky; He borrowed every dollar he could to buy as many Van Winkle bourbon barrels he could get his hands on.

Old Rip Van Winkle Bourbon of today

Julian P. Van Winkle III, far removed from the whiskey tradition his grandfather had embodied, was by no means a whiskey craftsman or even a connoisseur. But that didn't matter. All he needed to keep Old Rip Van Winkle alive was his ingrained memory of the old bourbon taste that Pappy had delicately forged. That isn't to say that Old Rip Van Winkle's success was certain or even probable. Julian had to bet everything on his instincts to help recreate Old Pappy Van Winkle's bourbon. And it was a gamble he had to take as it was his family legacy at stake.

After the whiskey industry had taken a turn for the worst, the Van Winkles struggled to keep their brand relevant and generate demand for their bourbon. The thing about whiskey is that it's easy to take a few shortcuts to make it a more viable business at the expense of quality. The new owners of Stitzel-Weller did just that, sacrificing good bourbon for the sake of their bottom line. That's because a distillery has a lot of overhead to deal with: Whiskey needs to be stored in a barrel for years or decades and a decent rickhouse manager is one in a million. All of those costs can accumulate and dry up a distillery owner's profits.

To keep quality high, Julian was forced to keep production low and find creative ways to save money. He worked in a derelict warehouse outside of Louisville and bottled Old Rip Van Winkle with his bare hands. This went on for years and Van Winkle remained an uber-niche bourbon distiller that barely turned a profit, if at all. But, Julian had held out as the company eeked by, producing just a few thousand bottles a year and gradually gaining recognition among sophisticated pallets. He personally taste-tested every barrel and stamped his approval on each bottle of Van Winkle he produced. That uncompromising quality control paid off and turned Van Winkle from a discreet brand into a stamp of provenance, prestige, and ultimate quality.

By 1996, Van Winkle bourbon made it on the map and was even a rendezvous point in the culinary world. It finally got the accolades it deserved that year when the Beverage Tasting Institute of Chicago rated Pappy Van Winkle's 20-year-old bourbon a 99. That unprecedented score kicked off Old Rip Van Winkle Distillery's modern reputation. The Pappy Van Winkle of today is a product of a partnership between Julian and the Buffalo Trace distillery, a deal penned in 2002 that only fruited a decade later when the first batch of Pappy Van Winkle's 10-year-old of the twenty-first century was bottled.