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How Pappy Van Winkle Became the World’s Most Coveted Bourbon

A conversation with Wright Thompson on his journey with the Van Winkle family.

Pappy Van Winkle collection of bourbons. Photo: Courtesy Pappy Van Winkle

For a time, it was like a secret handshake; a sign of recognition between two people that they both belonged to a sacred order. Wright Thompson’s baptism into the church of Pappy Van Winkle happened back in 2005, when his friend and acclaimed Mississippi chef John Currence introduced him to the bourbon that would become an obsession; so much so that Thompson, known for his longform journalism at ESPN, just wrote Pappyland, an entire book devoted to understanding this storied brand’s journey to its outsized status in the whiskey world.

“It’s not marketing, it’s the actual thing,” Thompson says. “At first it was this thing chefs were drinking. And there was this group of people and we were buying up all the Van Winkle we could. It was around then that we were like, ‘This is the finest bourbon in the world.'”

For a time, Pappy could be tough to track down, but far from impossible. Though it’s hard to believe now, a little more than a decade ago you could drink it in an airport. When Thompson wrote an article singing Pappy’s praises on ESPN’s Grantland, he told the story of a missed connecting flight. He trundled into a bar and ordered a glass of 15 on the rocks. With that request, the bartender knew a member of the congregation sat before him. “We’re out of the 15,” the barkeep told him as he dropped the glass. “This is the 23. Just the fact you know what it is, you’re worthy of it.”

By the end of the decade, word had largely gotten out that Pappy Van Winkle was the North Star for bourbon drinkers. Thompson’s Grantland article only fueled demand further. It became practically unobtainable after that.

While his article described the obsession he shared with fellow fans of the bourbon, it didn’t dive into how Pappy had come to be in the first place. Nor did it touch on the notion that Pappy’s success was never assured. The family behind the bourbon—the Van Winkles—spent years in the proverbial wilderness, as Americans largely lost their taste for whiskey. And at the time Thompson didn’t grapple with the fact that even at its new heights, the world’s most coveted bourbon may have been on the precipice of disaster; something that third-generation whiskey maker Julian Van Winkle III’s family knew all too well.

“Pappy” in this family is an actual person, Julian Van Winkle Sr., who owned the Stitzel-Weller distillery in the middle of the last century. There, Van Winkle the elder leaned on Kentucky wheat instead of rye in his mash bill, producing a smoother-tasting bourbon as a result. “His biggest contribution to modern bourbon is that he was the first to make and sell a mass-market fine whiskey with wheat as its dominant secondary grain,” Thompson writes in Pappyland. Eventually his son, Julian Jr., took over the business, but that was when whiskey’s popularity in America was fading fast. And eventually they’d sell off their barrels and brands. The family retained the Old Rip Van Winkle brand ,and when Julian Van Winkle III (the Julian we’ll refer to for the remainder of the story) took the company over, he was able to rebuild it into what it is today, relying largely on the bourbon his father and grandfather had distilled.

But there was a ticking time bomb. That old whiskey Julian relied on was running out, and he had to start making new bourbon. So in the early aughts, he turned to Buffalo Trace to distill and age what in 15 years would become Pappy Van Winkle. All the while he wondered if they could capture the flavor of that old Stitzel-Weller distillery bourbon. Thompson befriended Julian and tagged along with him as the company faced an inflection point in its history: tasting the new Pappy as it emerged from the barrel after 15 years.

We sat down to talk with Thompson about the Van Winkle family’s triumphs and failures, the role of myth in the world of bourbon, America’s whiskey boom and why your father’s bourbon may have actually been better than what we get today.

pappyland wright thompson book cover

Thompson stepped away from writing about sports to pursue another one of his passions.  Photo: courtesy Penguin Press

As you dug into the Van Winkle family history, you found the company was in some financial straits back before America’s whiskey renaissance.


They went way down in the hole. They borrowed so much money that they’re finally paying it all back this year—2021 will be the first year in the black.

Faced with that, why do you think Julian kept going, even after he saw how the business had bottomed out?

I think it was just trying to die with honor. I don’t think it ever really occurred to him this stuff would ever become popular or that they would become successful. It wasn’t about that. I think it was sometimes you owe your father something. Sometimes you owe your grandfather something. In this case, that meant going down with the ship. He was just trying to keep his family name from being dishonored.

What was the cause of the dip in demand for whiskey? Did the quality fall off and that’s why people stopped buying bourbon, or did people stop caring, so companies stopped investing?

It probably varied distillery to distillery, but at Stitzel-Weller the reduction in quality followed the reduction in interest pretty clearly. They knew they would have to lower the proof, for instance, because people weren’t buying it. And so Julian’s dad, they just held off lowering the proof until Pappy retired and Julian’s dad could take over. So Julian’s dad would take that bullet. It would never make his father be the one who had to do it, you know? And so there are a lot of reasons. I mean, some people literally talk about the James Bond effect that James Bond was the coolest man in the world and James Bond drank Martinis.

Was there a generational component to cratering whiskey demand?

Some of it was a wholesale societal rejection of your father’s America, that definitely played a factor.

What brought bourbon back?

There’s a way in which the history of bourbon played alongside the history of the American experiment. That’s a pretty interesting thing to do one day, just to sort of see—chicken and egg conversations—but where there is bourbon, there is always nostalgia. Nostalgia I found out recently comes from the Greek words for “homecoming” and “pain.” And I think many, many people on all sides of the political spectrum are in pain because they are missing a home that feels gone. And I mean, I do think big meta things like that are certainly at play. And some of it is probably just really, really sophisticated marketing.

Can you separate from how much nostalgia and the story colors your love of Pappy and just step back and judge the bourbon solely on its merits? How much do people love it because it’s “Pappy” and how much do people love it because it’s great?

I would say that any attempt to do one without the other is nuts. It’s sort of like when you’re talking about a restaurant, is it the room or the food? It’s always both, and because you’re asking to be transported that is physical and metaphysical. So I don’t think that when you’re talking about a bottle of Van Winkle, I don’t think you can strip its physical properties from its metaphysical property.

But do you think there’s a lot of mythmaking otherwise in bourbon?

It is interesting when you realize that you go to a liquor store and look at the hundreds of bourbon labels and six places distilled 95 percent of all of that whiskey. It’s pretty crazy.

That reminds me of when I sold watches after college and found out that so many of them at that mall store—from the cheap to the designer—were made by the same manufacturer and the only difference in price was the perceived value of the brand label slapped on it.

I hope this comes through with the book is that it’s both swimming in the myth of bourbon and interrogating it. Bourbon labels have always been a lie. The most modern phrase to me is the word “brand” and do you know where that comes from?

A cow getting branded?

Nope. Whiskey barrels being branded, because they used to put the barrels in bars.

Everybody who buys one of these bottles doesn’t mind that they’re being . . . What’s the right way to say this? Everyone is complicit in the mythmaking, and one of the things I respect about Julian is I have seen him do a lot of public speaking and he nearly always says every time, “I’ve never made a drop of whiskey in my life. My father and grandfather made whiskey.” Yeah, he is tasting barrels, helping design mash bills, looking for a flavor profile, but I don’t even know if he knows how to run a still.

Julian wasn’t actually distilling Pappy Van Winkle himself?

There’s a fundamental misunderstanding of bourbon. It isn’t made in the still, bourbon is made in a barrel. You and I could go make moonshine. The most important person, to me, in the bourbon-making process isn’t a distiller, it’s a warehouse manager—the rickhouse manager. It’s understanding how and where to put these barrels and managing a really long aging process. It is really hard to manage it.

And if you talk to bourbon industry people, Julian is not just a guy with a famous last name. His great palate gives him the ability to taste white dog or very young whiskey and figure out what it’s going to taste like. People talk with awe of his ability to do that. And in some ways, success has also taken on another one of his great skills, which was going around buying barrels of bourbon and blending them to get a flavor profile.

When the family sold off Stitzel-Weller, they got to keep the Old Rip Van Winkle brand name, so how did Julian go about building that business back up if he wasn’t distilling?

He was originally buying barrels of Stitzel-Weller—which everyone agrees is the finest bourbon in the world—that were just everywhere over Kentucky. I mean, to the point that Diageo was using Stitzel-Weller bourbon as two percent of the Crown Royal blend. They were throwing it away.

Julian was borrowing as much money as he could to buy as much of it as he could. He had banks in Kentucky [that] wouldn’t loan him the money: “What do you want this old bourbon? It’s worthless.”

Stitzel-Weller Distillery

Julian Van Winkle Sr.’s Stitzel-Weller distillery is now owned by Bulleit.  Photo: courtesy Timothy Joseph Wood/Creative Commons

So he had the palate to recognize that the Stitzel-Weller barrels his family had sold off were legitimately special—it’s not just nostalgia why this old bourbon was great. Why does it taste different than what’s made now?

If you get on the Internet, buy an old bottle of bourbon—not fancy bourbon—but just go buy a $40 pint of Old Charter from the ’70s, it’s just different than what’s being produced now. It’s because the way the grains are ground is different, the yeasts are different and the water is different. They polluted all the limestone aquifers in Kentucky so they have to use an ionized water now. So it’s clean, but there’s something that’s forever missing. Pollution just forever changed that. You know, Stitzel-Weller sits on top of the big old limestone aquifers, but that whole world is gone.

There are all sorts of ways in which the bourbon of the past, which no one wanted, is specifically and legitimately superior to the bourbon now, which everyone loves. One of the things that Julian is forever after when he’s smelling and tasting the barrels that will or will not become Pappy—and some of them they just dump—he is not looking for a technically perfect thing. He is just looking for something that comes as close as he can get to his memory of what the whiskey his father and grandfather made at Stitzel-Weller smelled and tasted like. Each bottle is a memory quest. And so when I open it, it is both full of melancholy and an antidote to melancholy. I like that.

But when you drink a Pappy 15 now, you’re not getting that Stitzel-Weller juice that Julian’s keen palate could select, right?

He smartly realized around 2001, 2002 that he was going to run out of the Stitzel-Weller. Other people were buying it, the price was going up and it was running out.

Is that where Buffalo Trace comes in?

The family went into their partnership at Buffalo Trace to develop a wheated mash bill that was Julian’s attempt to make sure this wasn’t just a thing that died—a relic of a boom. The book is me riding shotgun as they prepared to put out the first Pappy Van Winkle that is Stitzel-Weller mash bill made at Buffalo Trace.

It’s a moment 15 years in the making, waiting to see if it worked.

He’s freaking out, because what if he hates it? They designed the mash bill, they tasted off of the still . . .

You were there tasting with him. How was it?

Unbelievable. We all were just like, “This is as good as anything in the world.” When Julian’s tasting, he’s like, “This isn’t Stitzel-Weller, but it’s really close.” He was really happy. Everybody did their jobs.

I mean, he would only cop to nervousness after. If it sucked it would have been a real problem, I don’t know what they would have done. Because it’s not like they can just go out of business. He just would have had to probably lie in public and he’s really bad at it.

Would he have been able to?

The guy has no fucking poker face, and so he would have gotten caught almost immediately. Everyone dodged a bullet!

Julian Van Winkle III and Wright Thompson

Julian Van Winkle III and Wright Thompson  Photo: courtesy Thom Shelby

With how much people covet this bourbon, do they wish they would have made more?

Julian is putting whiskey in barrels right now, and he’ll be dead before they’re bottled. He is trying to hand the business over to his son, and he knows from family experience what happens if you’re caught on the wrong side of the bust. But lot of people don’t have that experience, and so there’s this clamor: “Why don’t you make more?!?” And I think Julian’s answer would be, “I don’t know if you guys are going to want it when it’s ready.” So he’s very conservative about that in a way that’s really interesting. I mean, I’ve spent a lot of time and I’ve asked him couple of times, “What do you think this thing’s going to pop? What is the bubble going to pop?” And he goes, “I thought it was going to pop years ago. I’m stunned we’re still doing this.”

Will bourbon fall by the wayside again, when our kids dismiss it saying, “Ugh, that’s what my dad drinks”?

Of course it will. And what’s so interesting is 20 years ago, Julian was making 2,500 cases a year. Now they’re making somewhere between nine and 10 thousand and they still can’t keep up with demand. In 50 years Preston Van Winkle, one of his sons, will be running this distillery making bourbon and maybe it’ll be popular and maybe it won’t, but I don’t think they’ll ever overproduce trying to catch the ride of a wave. It’s a long game.

And I just wonder to the degree that people whose business is trying to wait 15, 20 or 23 years on something and predict what America is going to want in 15, 20 or 23 years predisposes them to not get caught up in quarterly earning bullshit. I just wonder if the business still selects people who can take the long view or if you were just forced by repetition and trauma to take the long view.

But it is interesting to me how the real old-school people in this business are very resistant to fads and sort of unaffected by buzz. It doesn’t register in their world and in a way that folks like me and you, who are on the outside looking in, would think it would register. There isn’t a mania in these offices. They don’t believe in a gold rush.

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