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

Pappy Van Winkle is the nostalgic old-school bourbon that most whiskey hunters would kill to get their hands on. But is it the right racehorse to bet on?

Guy Ovadia

Published Aug 22, 2022Updated Aug 31, 2022

Whiskey

Whiskey

Collectibles

Collectibles

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Global Markets

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?

The general rule when it comes to procuring Pappy's is the older, the better, but that doesn't mean bourbon that's aged longer is better to invest in…

A lot of it comes from the mythos surrounding the family-owned brand. Julian Prentice Van Winkle, Sr., AKA "Pappy," worked in the whiskey business his entire adult life. Starting as a traveling salesman for Weller distilleries, Pappy worked his way up to part-owner of the company in a decade and a half's time through the dawn of the 20th century.

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

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Source: topbourbon.com

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'.

Another factor that made Pappy's bourbon of higher quality was time. Most bourbons aren't aged for as long as Pappy's is due to avaricious concerns around profitability. Pappy was a man of passion for his craft and wasn't one to cut a corner for an extra buck. Other whisky brands looked for ways to reduce costs and make up for what their products lacked with marketing, but Pappy upheld quality first and put business second, for better or worse. Pappy's focus on quality would eventually make the Van Winkle name more than a brand, but a mark of distinction, even to its detriment.

Why Van Winkle bourbon is rare

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.

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Collection of Old Rip Van Winkle bourbons offered for $14K on Rally. 

Source: rallyrd.com

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.

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Julian "Pappy” Van Winkle, Sr. with Julian Van Winkle, Jr. and Julian Van Winkle III at Stitzel-Weller Distillery circa 1958.

Source: gobourbon.com

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 Winke'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.

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From left to right: Julian "Pappy" Van Winkle, Sr.; Julian P. Van Winkle, Jr.; Julian P. Van Winkle III.

Sources: buffalotracedistillery.com, oldripvanwinkle.com, gardenandgun.com

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.

Best Van Winkle whiskeys

Though the process today isn't identical to how Pappy had made it, it nearly replicates the Old Van Winkle flavor by using the original mash-bill, filtering water with a limestone substrate, and deploying a stringent tasting process. The Old Rip Van Winkle brand remains loyal to its roots by putting quality before everything else. It's evident that profits weren't on the priority list either when comparing the $300 retail price of a bottle of Pappy Van Winkle's bourbon to the thousands they go for in the aftermarket. 

The most important thing upheld by the Van Winkle legacy is scarcity. Julian had kept production of Pappy Van Winkle's very low because it took so long to produce whiskey and he didn't know what the demand would be by the time it gets bottled in ten, fifteen, or twenty years' time. Pappy Van Winkle's eventually grew to be the most coveted wheated bourbon, and that desirability further expanded into mass-market appeal. And despite all the hunters trying to get their hands on a bottle of Pappy's Family Reserves, only a handful of the few thousand bottles reaching local liquor store shelves each year aren't already spoken for.

Breeze or Blowout.

Breeze or Blowout.

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Pappy Van Winkle's Family Reserve

The general rule when it comes to procuring Pappy's is the older, the better, but that doesn't mean bourbon that's aged longer is better to invest in (although it might taste better). The best way to demonstrate is to look at Pappy Van Winkle's Family Reserve, Old Rip Van Winkle's Distillery's flagship bourbon.

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Chart tracking Old Rip Van Winkle's Family Reserve 23-Year price. 

Source: wine-searcher.com

For instance, a newer bottle of 23-year-old Family Reserve comes at a price of $5,000 or more on the secondary market (though it's usually auctioned for cheaper), while the price of a 1991 vintage Family Reserve 17-year-old is in the $30,000 range if you can even find it. While you can do some serious retail arbitrage with a rare bottle of new Pappy Van Winkle's bourbon, the real value is in Pappy bottles from older vintages since they're harder to find.

Pappy Van Winkle's Handmade Family Reserve

As you look at older Van Winkle vintages, they get scarcer and harder to find since there are fewer of them around. As interest in Van Winkle bourbons really picked up over the last couple of decades, sought-after bottles like the Handmade Family Reserve and the Family Selection reached higher prices, despite retail prices staying pretty much the same.

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Chart tracking 1991 Pappy Van Winkle's Family Reserve 17-Year price. 

Source: wine-searcher.com

Old Rip Van Winkle's Handmade Family Reserve vintages from the 1990s are probably the best bourbons you can invest in right now. Prices for these bottles vary radically, starting at $10,000 at auction and reaching up to $40,000 at some aftermarket sellers. Prices for Pappy Van Winkle's Family Selection also fall into a wide range, going anywhere from $30,000 to upwards of $40,000 depending on if they include the branded glasses and decanter.

Rip Van Winkle's Special Reserve

At the far end of the Van Winkle's price range are the Special Reserve Corti Brother's 20-year-old and Old Rip Van Winkle's 25-year-old bourbons. Both of these super rare Van Winkle bourbons go for over $50,000—if they're available—since they're more relics of Van Winkle's venerable past than actual drinking beverages. That price is set by the few people willing to sell their bottles, so it's unclear if they'll appreciate or even retain their value if you buy them. You should only invest in these if you're a serious bourbon hunter or can afford to buy such an extravagant-yet-subtle artifact.

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Chart tracking Old Rip Van Winkle 25-Year-Old Straight Bourbon price. 

Source: wine-searcher.com

Other ways to invest in Old Rip Van Winkle 

Though these prices make the $300 ESRP sound reasonable, it's obvious that bottles like these are too exorbitant for most people to afford. Even if you have the money, whiskey is hard to break into for investors since it's historically been an opaque boys club and writhe with scams and fake bottles. That's why investors who aren't too shy to ask experts for help use investing platforms like Vint and Rally.

rallyrd
Rally

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Watches

Rally is a platform where investors can buy fractionalized shares of collectibles including bottles of fine wines and luxury whiskeys such as the Macallan scotch and Old Rip Van Winkle bourbon. An assortment of five Old Rip Van Winkle bottles—including Family Reserve 10-year, 12-year, 15-year, 23-year, and 13-year-old rye—were offered to investors at $7 a share. This collection of Old Rip Van Winkle bourbon bottles was valued by Rally at $14,000, making each one worth around $2,800. 

When the offering was made publicly available on August 13, 2022 it sold out almost instantly. Old Rip Van Winkle has practically flown off the shelves in recent years, so Rally's offering illustrates how desperate investors are to gain exposure to this lucrative asset. However, there's no guarantee that their investment in Old Rip Van Winkle bourbons will be everything they dreamed of.

vint
Vint

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Collectibles

But if you're still on the prowl for some Pappy's, then you should keep your eyes on other spirits investing platforms like Vinovest and Vint. Vint is a platform that lets you buy shares in collections of luxury whiskey and fine wines. Though they don't have Van Winkle bourbons available right now, their collections are open to investors for a limited time until they're sold out. Vint shares start at $50 and they expertly manage your investment, which makes it one of the easiest and most accessible platforms for investing in luxury spirits.