All September on VinePair, we’re turning our focus to America’s spirit: bourbon. For our third annual Bourbon Month, we’re exploring the industry legends and innovators, our favorite craft distilleries, new bottles we love, and more.

The 1980s were a difficult time for Julian Van Winkle III. After joining his father in the family business in 1977, just a few years after graduating college, he found himself taking over the J.P. Van Winkle & Son company after his death. He was 32 years old with a wife, four young children, and an influx of bourbon that few folks wanted to buy. Thus, he would move his stock from Yellowstone, Old Boone Distillery, and especially Stitzel-Weller any way he could.

“I had to survive somehow,” Van Winkle recalls. “Back in those days, the whiskey wasn’t important — what was important was what it came in.”

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Early on that meant putting it into gimmicky decanters shaped like college mascots, selling it to an unexpectedly willing Japanese audience, offering personalized bottles with hand-scribed calligraphy (“a pain in the butt” claims Van Winkle), or even doing private label bottles for places like Chicago’s Berghoff Bar, which was said to be his biggest customer at the time, and Corti Brothers, an Italian grocer in Sacramento, which purchased two single barrels of Van Winkle Private Reserve in 1986.

“Julian sent me samples, and I bought them from those,” claims proprietor Darrell Corti, who asked that they be packaged in classy Cognac-style bottles from a nearby winery.

Those bottles were put on his store shelves for $20 and he had trouble selling them, taking nearly two years to move the couple hundred bottles. Corti knew it was great bourbon, but future Van Winkle private bottlings would likewise sell slowly when he offered them throughout the late-1980s up until 1994, when Corti’s released a 20-year-old.

“As far as I know, we were the first to privately select a Van Winkle.”

He certainly wouldn’t be the last.

By the late 1990s, Julian Van Winkle III was starting to have some success. That was kickstarted by his first-ever release of Pappy Van Winkle’s Family Reserve 20 Year in 1994. Taking inspiration from Corti, Van Winkle placed the liquid in Cognac bottles and charged a then-whopping $80. When the bourbon scored a 99 out of 100 at the Beverage Testing Institute’s 1998 World Spirits Championship, it was instantly put on the radar of connoisseurs.

By the 2010s or so, Pappy would be a veritable ‘unicorn,” mostly impossible to find at retail — and, if you really wanted it, you would have to pay hundreds if not thousands of dollars on the secondary market. That’s for a single bottle.

But just a decade earlier, beginning back in 1999, Van Winkle was still trying to offload single barrels of his 10-year-old stock for a mere $1,200 all-in, even taking to the message board — a gathering place for early enthusiasts — to see if he could gin up any interest. (Van Winkle doesn’t recall that, but you have to remember, even for him — especially for him! — the bourbon world has changed radically over the last two decades.)

“At that time, it was still pretty easy to find the Van Winkles; most good liquor stores had a Pappy or two and the 12 year old Lot B was downright plentiful,” wrote whiskey blogger Steve Ury back in 2014, fondly recalling the era.

And, there still weren’t a lot of people who really saw the need to stockpile a lot of it.

Though there were a few early adopters who wanted their Van Winkle in bulk.

Van Blankle

Randy Blank, a chemical engineer from Houston, was no Johnny-come-lately to the scene; he had been a fan of Stitzel-Weller bourbon since the 1980s, even serving Old Fitzgerald Bottled in Bond at his own wedding.

“The retailers and restaurants were already doing single barrels,” recalls Blank. “When I saw that and tasted them, I thought, wow, maybe that’s something an individual could do.”

In 2004, Blank emailed Julian Van Winkle III asking if he could do his own private bottling. Van Winkle liked the idea, but admitted he had never done them for any individual before. Buffalo Trace, meanwhile, who had begun a partnership with Van Winkle in 2002, was hesitant to do it — at that time they were interested in getting the product to more markets.

Blank was a fan of 107 proof Old Rip Van Winkle 10 Year Old, but Van Winkle advised against it. Stitzel-Weller — once run by his grandfather Julian “Pappy” Van Winkle Sr. — quit distilling their legendary wheated bourbon by 1992 and if you subtract that from the year 2004 you get 12. Indeed, Van Winkle advised Blank that Van Winkle 12 Year Old Lot B would be the youngest product available consisting of Stitzel-Weller juice.

Blank headed up to Buffalo Trace Distillery in Frankfort, Ky., and tasted through five barrels distilled in March of 1992, opting for a more approachable profile (“smoother and lighter” he once recalled) as he planned to give away most of the bottles as gifts. The barrel produced 17 12-bottle cases and cost Blank about $7,000 — around $33 a bottle.

“I figured I had a lifetime supply,” recalls Blank.

However, the next year, the whiskey cognoscenti on the forums had already begun discussing the greatness of what was now cheekily dubbed “Van Blankle.” Many posters — where Blank was an active poster himself — first tried it at a bottle share at the Best Western during that spring’s Kentucky Bourbon Festival in Bardstown. Blank had given many of his StraightBourbon buddies a free bottle and some compared it to a fine Cognac due to its delicate, sweet flavor profile. By 2015, the few remaining bottles of “one of the best, if not the best private barrel pick of Lot B” were selling for upwards of $2,500.

Seeing how good Van Blankle was, several other groups of StraightBourbon posters over the next several years would head to Buffalo Trace to buy their own single barrels, including in 2007, when the Kentucky Barrel Society picked one of the first and only single barrels of Pappy Van Winkle 23 Year.

“He started a domino effect for what we have today in the bourbon world,” claims Kristopher Hart of the “Whiskey Neat” podcast. “Randy is directly responsible for the environment we have today with private barrel picks.”

Before It Became a Unicorn, Pappy Van Winkle Was Sold By the Barrel
Pappy Van Winkle

Me and Julio’s Down in Frankfort

There’s a television commercial that would have aired around the greater Boston era during this time in the mid-aughts. In the spot, Ryan Maloney, the owner of Julio’s Liquor in Westborough, Mass., walks the viewer through his 36,000-square- foot store, touting all the great wine, craft beer, and whiskey they stock.

“Some from my very own barrels!” he explains in the commercial, turning around to pull a bottle of his own single-barrel pick of Pappy Van Winkle 15 Year from the shelves. “Of course, today if people saw that, they’d say, ‘Holy crap, are you kidding me?!’”

Another early player in the single-barrel game, Maloney’s family had owned Julio’s since 1974. Maloney’s father was more of a wine guy, though he did have a taste for quality whiskey and stocked plenty of it. When Maloney began running the place in 2000, he began focusing on acquiring single barrels from his favorite distilleries; he believed then, as now, that they are great calling cards to introduce people to a brand’s entire portfolio.

“I was buying stuff I knew would sit on our shelves for months, even a year,” says Maloney. In 2004, Al Zarrella, Maloney’s Sazerac rep at the time, asked if he wanted to come down to Frankfort to see some Rain vodka being bottled. “I told him, ‘Al, you’re asking me to fly to Kentucky, with no direct flights from Boston, to watch a clear liquid get put into a clear bottle.’”

What Maloney suggested instead was that he come down to buy his own barrel of bourbon for his store. Buffalo Trace, which had just started a single-barrel program in 2002, was eager to have him. Maloney ventured down in the spring of 2005 and tasted through some wheated bourbon barrels — he recalls then-master distiller emeritus Elmer T. Lee sipping with him — and found plenty to like.

“But I knew I had to seperate my passion from my wallet,” meaning, buying entire barrels costs a lot of money and Maloney knew they wouldn’t move from the shelves at any sort of brisk pace. Few customers at the time even knew what “single barrel” meant.

“I understood that this would be a hand sell,” recalls Maloney. “People weren’t clamoring over this stuff like they are today. I had to take a giant leap of faith.”

It seems silly to claim, in these days when most liquor stores are lucky to get a single 3-pack case of the entire Van Winkle line each year, that immediately accessing some 150 bottles of Pappy at once would be a “leap of faith.” But indeed it was back in 2005.

Maloney ended up buying a barrel of Pappy Van Winkle 15 Year and additional barrels of Weller Centennial — with the exact same mash bill as Pappy — that were 13 and 14 years old. Unlike today, where private barrel buyers love to attach silly “tater stickers” and garish wax to their “picks,” back then a subtle decal, courtesy of Buffalo Trace, was added to the neck, simply reading:

Julio’s Liquor
exclusive hand-picked

​​For the next few years, Maloney would pick an additional single barrel of the 15 every year. By 2008, his final year to pick Pappy — “you could sense barrels were starting to get more rare” — the bottles now had a decal denoting it was for The Loch & K(e)y Society.

Allocated whiskey was finally becoming a thing and Maloney had recently started an in-store club so that top customers could taste through and buy more limited offerings. He and Julio’s were well ahead of the curve — today he hosts a special online auction for his top customers to sell his limited allocation of the Van Winkles.

“A single barrel is an anomaly,” says Maloney, meaning its flavor profile is inherently going to be a little different from the usual release composed of many barrels blended together. “So you’re looking for an anomaly that tastes good. I always felt the barrels we picked were the best examples of what we thought was the ideal Van Winkle.”

Peel Away the Husk

“There was no rhyme or reason, no game plan,” says Julian Van Winkle III, as to who got Van Winkle single barrels throughout the late 1990s and early 2000s. He, and later Buffalo Trace, were still trying to sell bourbon any way they could. Van Winkle estimates it was just a few dozen retailers, bars, restaurants, and individuals in his top markets who got these single barrels between that 1986 Corti’s pick and the end of this program in 2011. “There were less than 50. But more than 20.”

Jamie Marcus, a Massachusetts-based collector with a specific interest in acquiring Pappy Van Winkle 15 Year Old single barrels, has confirmed that at least 13 of those occurred between 2002 and 2010. In 2002, before even Julio’s first pick, the now-shuttered Civic Center Market in San Francisco did a 15 Year pick, the first ever Pappy Van Winkle single barrel packaged in a Cognac-style bottle.

“[There’s an] anecdote that the owner and customers involved in the pick were expecting Old Rip Van Winkle 15 Year squat bottles and nearly returned the Cognac bottles because they had never seen them before,” claims Marcus. Instead, proprietor Edmond Kubein put bottles on sale for $34.99 — and they still sat there for years.

“And then the craze came and people started coming out of the woodwork searching for them,” Kubein recalled in 2018. He says he plans to be buried with the final two bottles in existence.

There were still private-label single barrels, too, like Binny’s in Chicago and New York’s Park Avenue Liquor Shop, which both bottled 18-year-old Van Winkle Special Reserve in 2003. That same year, Blue Smoke, Danny Meyer’s upscale BBQ restaurant on Park Avenue, would get a private-label Old Rip Van Winkle Blue Smoke 18 Year — it was available at the restaurant for years, but would end up being one of the most coveted Van Winkles from this era.

There was Jackson’s Wine and Spirits in Lafayette, Calif., which picked a Pappy 15 Year in 2007, and West End Tavern in Boulder, Colo., which did likewise in 2009 (though the liquid may have been 17 years actually). By the time that Cask, also in San Francisco, did a 15-year pick in 2010, they were charging $79.99 a bottle.

These barrels were usually a lot older than the age statement, too — one reason they continue to be so acclaimed today — like in the case of what ultimately became maybe the most famous Pappy pick.

By the fall of 2010, as chef Sean Brock was preparing to open Husk in Charleston, S.C., he got in touch with Julian Van Winkle III, who he deeply admired. Brock — one of the country’s first true Pappy zealots — aspired to stock his high-end Southern restaurant with an ample supply of the Van Winkle line, and this was just around the point when that was becoming impossible through standard measures.

Luckily, Van Winkle allowed him to grab a full barrel of Pappy 15 Year, though its contents were said to be 19 1/2 years old and some of the final Stitzel-Weller stock in his possession. The rumor was that, in order to pay less taxes, Julian Van Winkle III found Brock the oldest barrel he could under the 20-year cutoff for the next tier of bottling. (For the record, Van Winkle doesn’t recall this whatsoever and told me it didn’t sound likely.)

Whatever the case, glasses of Husk’s single barrel sold briskly, with Brock often flexing for his friends and famous chef buddies with gratis pours. Still, it managed to last for a few years, and today the barrel head is still proudly displayed at The Bar at Husk.

Crazy Stupid Hype

These glory days of “Private Pappy” would last less than a decade in this final era before the bourbon hype machine began firing on all cylinders.

Just after Husk’s pick, in 2011, Julian and his son Preston Van Winkle joined Oxford, Miss.’s renowned chef John Currence to select a 20-year-old barrel of Pappy to honor the 20th anniversary of his restaurant, City Grocery. A mere 83 bottles were able to be milked from the barrel and, by then, local Mississippians were clamoring to nab one of what Van Winkle called at the time “the best whiskey we have ever made. That’s the barrel you want!”

Within the year, Pappy-mania had fully heated up and Julian Van Winkle III was now offering mea culpas to fans who couldn’t score bottles, like at 2012’s Charleston Wine + Food Festival where he told the audience: “We apologize for the scarcity. Most of the liquor stores are mad at us, and the consumers are mad at us, too.”

By 2013, Van Winkle’s Stitzel-Weller barrels would be almost completely exhausted and bottles would now consist of 100 percent Buffalo Trace distillate. Even if many fans thought it was no longer quite as tasty, every year it became harder and harder to land bottles as Pappy became more and more a household name, written about by Wright Thompson; namechecked by Anthony Bourdain; even served by hunky Ryan Gosling’s character in “Crazy, Stupid, Love.”

No matter how many barrels of Pappy you had sold in the past, no matter how friendly you were with Julian Van Winkle III, you were never again going to get a single barrel for your store or restaurant or daughter’s wedding. Buffalo Trace didn’t even have enough supply to meet the regular demand.

Today, many of those scant single-barrel bottlings from the past have been lost in the shuffle. Even Marcus, who has dedicated the last several years to the pursuit, has been unable to confirm five other rumored Pappy 15 single barrels.

“Whenever I try talking to someone about 15-year, single-barrel Pappy these days, you’d think I’m trying to find Keyser Söze — people get real quiet real quick,” jokes Marcus.

And that’s one reason why the few known bottles sell for insane amounts at auction.

A Corti’s Van Winkle was recently auctioned off for some $30,000. The Blue Smoke 18 Year has gone for upwards of $24,000. One of the last 18 bottles of City Grocery’s single barrel went for $6,000 in 2019. While West End Tavern is literally down to the final bottle left from their 2009 barrel. It sits behind a glass case at their bar in Boulder, seemingly never to be sold for the rest of eternity. Marcus even offered them a small fortune when they needed revenue during pandemic lockdowns, but they respectfully declined.

As for Julian Van Winkle III, he has fewer Pappy Van Winkle single barrels than you might think.

“I’ve got a few bottles left, but I don’t dare open them for the obvious reason. The other reason, though, is because it’s frustrating that that whiskey was so good,” he says, recalling the single barrels days.

“It was a fun time, and I do sorta miss it.”