The other day I’m buying an exercise bike from a guy when I see his whiskey collection. It’s a nice one, a few shelves’ worth. The topic of Pappy Van Winkle, that white whale bottle with an enormous price tag, comes up. I ask him if he thinks it’s possible to find one at a price that wouldn’t make my nose bleed.

Ha.” It wasn’t a laugh really, just an exclamation. “Not gonna happen,” he says.

Technically, bottles of Pappy Van Winkle start at $130. But you’d be hard-pressed to find one for less than ten times that, even at legitimate liquor stores that work directly with Buffalo Trace, Pappy’s parent distillery. Older expressions — like the crème-de-la-crème 23-year-old, which should cost $270 — can top $3,000, easy. That’s more than a month’s rent where you’re drinking it.

This is no new story, of course. The phenomenon that is Pappy Van Winkle has been going on for nearly a decade. But if you’re a certain type of person, like, say, a journalist, hell no, you’ll never find it feels more like a challenge than a warning.

As I haul the bike into my car, I wonder whether I could do some digging and come up with a bottle of the stuff for retail, or close to it. You heard tales of it happening, maybe a few years back. But surely there are some unicorns left on dusty liquor-store shelves or connections I could tap into on the black market.

So a few days later, I convince my editor to give me $300. The challenge, we agree, would be to buy a single bottle of 15-, 20- or 23-year-old Pappy using that sizable lump of cash.

How hard could it be?

Pappy is more folktale than whiskey nowadays. Its namesake is Julian “Pappy” van Winkle, a slick bourbon salesman in the 1890s who eventually became the president of the Stitzel-Weller Distillery in Kentucky. His son and Grandson, Julian Van Winkle, Jr. and Julian Van Winkle III, ran the distillery until the family sold it in 1972, but kept the family name alive in the bourbon business by buying back old barrels from Stitzel-Weller and other distilleries and bottling it under the Old Rip Van Winkle label. In the 1980s, Van Winkle The Third started bottling blends of really good, really old bourbons. Eventually those became the modern line of Van Winkle bourbons, including the three oldest ones: Pappy Van Winkle’s Family Reserve 15-, 20- and 23-year-old. Today whiskey drinkers simply call them “Pappy.”

As for how Pappy Van Winkle became the most-hyped bourbon ever: that appears to have started in 1996, when a sales rep in Chicago entered the 20-year-old whiskey into a Beverage Tasting Institute panel. The whiskey was awarded a 99 out of 100, the highest score ever for bourbon.

Bourbon was just beginning to boom in the late 90s. In 2002, the Buffalo Trace Distillery (owned by Sazerac), which was already supplying some of the whiskey for the blend, took over distilling full-time. Rave reviews started really rolling in. Among whiskey drinkers, Pappy became a poster child for the high end of quality. Then came the final rail in the hype train’s tracks: In a 2012 episode of his show The Layover set in Philadelphia, Anthony Bourdain ordered the 20-year-old with one rock. Watch the moment and look at Bourdain’s eyes when the waitress says they have it; they light up like sparklers. Bourdain called it “That incredibly wonderful bourbon whose name I’m not gonna mention because there are just too many sons of bitches out there who want it,” and later tweeted that he was considering getting a full-back Pappy tattoo. Demand exploded.

The Pappys, all lined up. From left to right: 10- and 12-year (both not technically “Pappy”), the 15-, 20-, and 23-year-old.

Supply, meanwhile, stayed insanely small. Word on the street is Buffalo Trace only produces around 7,000 cases a year, or something like 84,000 bottles. (Buffalo Trace would not confirm this.) Ballpark, that’s less than 10,000 bottles per state. Compare that to roughly 84 million bottles annually of Jim Beam — a million and a half bottles per state.

Absurdly high demand, absurdly low supply. Better whiskey writers than I have outlined the economics of it, but really any sober economist could tell you the result: Absurdly. High. Price.

The rest of us, well, we’re left wondering just how good the stuff tastes. What’s actually inside those bottles has always been a closely guarded secret. The original stocks of Stitzel-Weller juice appear to have been used up in the early 2000s. The Buffalo Trace version is still a wheated bourbon, with a higher concentration of wheat than rye, which ought to give it a more velvety mouthfeel and complex sweetness. In fact, Sazerac has confirmed it’s got the exact same mashbill as Buffalo Trace’s other wheated bourbons (like Weller).

But fifteen or twenty years or twenty-three years is an extraordinarily long time for bourbon to sit in new American oak casks, soaking up delightful flavors. Both Bourdain and the Pope — plus some of my favorite whiskey experts, like Jim Murray and Fred Minnick — have assured us that it doesn’t taste like licking an oak stave. They tell us, in short, that it tastes like heaven.

I had it once, the 15, at a friend’s wedding. I was so drunk I can’t remember anything about it except the burn. Whoops.

The most obvious way to get Pappy close to retail price is through a state-run lottery. To avoid all sorts of black-market shenanigans (more on that soon), a handful of states — most of them have state-run liquor stores — only sell Pappy to lucky winners.

I find this out standing in my hometown’s liquor store in Camp Hill, Pennsylvania, where I’m home visiting family. California, where I live, doesn’t have a lottery system for bourbon. But Pennsylvania — home of some absurd blue laws, and where they just started selling beer at grocery stores a few years ago — controls its liquor with an iron fist. The guy at the Camp Hill store says he’s never even seen a bottle of Pappy in person, but he also tells me that the winner of the state lottery could buy the bottle for retail, plus a small markup, an emergency tax of 18 percent, and a handling fee.

I walk out of the store with the flush of a successful riverboat gambler. Here is my shot! But then the adrenaline wears off, and the bottles of affordable, incredible bourbon stop dancing through my head, and I think, I’d better look into this. Turns out you have to be a resident of the state of PA to enter the lottery. But no problem. There are plenty of other states where you can enter the lottery and not be a resident. New Hampshire, for instance, where you can donate $100 to a charity and be entered into a small-ticket raffle to win the entire suite of Pappy.

Of course, that would be the bulk of my Pappy money gone. My exhilaration for the lotto game slows. Anyway, isn’t a lottery a gutless way to go about finding this? If I won, it wouldn’t be any story at all — just blind luck. I might as well have found my bottle of Pappy lying on the ground like a dirty five-dollar bill. Without the chase, would I really even be excited to drink it? Hell, wouldn’t I be tempted to turn my lottery winnings into $1,000 by selling it at street price?

I do not enter any state lotteries.

The next obvious place to look for a bottle of Pappy is, of course, to google that shit. And that is how quickly I entered the not-so-dark underworld of the black market for bourbon.

A quick thought on ethics here. Yes, it’s illegal to sell or buy liquor secondhand without a license. It’s also illegal to live-stream NFL games using a reddit thread. I might pay $900 for a bottle of bourbon, but not for a Red Zone package. The cops don’t agree, though. In 2017, a dude trying to sell a bottle of William Larue Weller for $750 on Craigslist (not a bad price!) in my home state was arrested after police set up a sting.

A bottle of Pappy 20-year and its trademark red velvet bag.


But rather than going full The Untouchables, it appears the feds would rather just turn off the biggest online marketplaces for the stuff. People used to sell bottles on eBay; that got shut down years ago. I hear myths about private Facebook groups where the Pappy flows like cheap wine. Back room deals, meetups to drink the stuff. All shut down — or maybe I just can’t find them. Bottlespot.com, a Kelly Blue Book type site, helpfully tells me the market rate for the 15-year was really closer to $900, but offers no help in finding it. The last tweet by @PappyTracker, a twitter account made to spit out Pappy-finding tips, is for a state lottery in 2018.

Craigslist, a spot I figure would be hot, shows me I’m surrounded by a Pappy desert: just two posts asking to buy the stuff, plus one guy selling the red velvet bag the bottle comes in for $35.

I email the bag guy. “I actually was able to buy a couple bottles a few years before it became famous,” he writes back, refusing to give his name. Near-retail price, for the 23-year bottle. Grail stuff.

“I feel it is totally over hyped and way over priced for sure,” he says. “To be honest, not worth the hassle of trying to find them.” He does have a second bag he’d sell me, though — I can have the pair for $70.

I just moved to LA, but I’ve already found one good liquor store within walking distance. The beer selection is good, the faces behind the counter are smiling and the bottles up high on the shelf are impressive, with prices that seem right.

I head over and ask the guy I’ve met before behind the counter about finding Pappy. Big mistake. Suddenly, he won’t look me in the eye. Why?

I spill that I could never afford a bottle, probably, but I’m curious about the way it all works. The counter guy looks me in the eye again. He tells me he used to work as a bartender, and he had a vendor hookup who got him bottles. I tell him I’m trying to find out more because I’m a writer, doing a story on Pappy. He smiles. “I’m a writer too,” he says. Gotta love LA.

Bolstered by bonhomie, my new writer friend starts telling me all kinds of stuff. Starting with the fact that the price for the 2019 15-year Pappy, bought in-store when they got it in early November, would be… He double-takes his computer screen, then laughs maniacally. “Sixteen.”

As in, sixteen hundred dollars? He nods, like he can’t bring himself to say the extra two zeroes. In a conspiratorial whisper, he tells me he thinks the 15 is better than the 20 or 23. And those ones cost three grand.

I pick his brain about how this all works. The vendors, he says, are key: they’re the ones who decide the distribution of the stuff, which is the whole game. For stores to get a bottle of Pappy, they have to sell a certain number of pallets of all of the rest of Buffalo Trace’s bourbon and Sazerac’s portfolio at large. Given the scale of the operation, Sazerac and the vendors don’t make that much money off of Pappy; it’s about power. The message to liquor store owners: sell well the rest of the year, and we’ll help you make a nice Christmas bonus. (Buffalo Trace confirmed that wholesalers determine distribution.)

On my way out, I buy a bottle of Willett 4-year rye for $60, which feels like a good find. The counter guy gives me a tip: there are one or two liquor stores that might have a bottle of Pappy in a back room, saved for the owner, or the owner’s friends. These liquor stores, he tells me, are fronts for rich guys who want to clean their money.

As a rule, I try not to entangle myself with shady businesses. Asking a purported money launderer for a deal on a bottle of whiskey feels like a one-way ticket to run errands for the mob.

Then again, people have committed serious crimes to get their hands on some Pappy. In 2015, police in Kentucky busted a ring of nine people, including Buffalo Trace employees, who had stolen upwards of $100,000 worth of Pappy and other whiskies over a span of five years. The ringleader of what became known as “Pappygate” apparently nabbed 200 bottles from its storage lockers by removing the pins from the rusty old doors. (He also fired a silenced pistol in the parking lot to intimidate other employees and was very, very into selling illegal steroids.) The ringleader pleaded not guilty and got 15 years — and then was released for probation 30 days into his sentence. (Does the judge drink bourbon, perhaps?)

So before getting illicit, I try the vendors. I call and email. They don’t respond. Maybe they don’t want to spill their trade secrets to a nosy writer.

I’m short on leads. I could canvas more random liquor stores. Instead I crack and call up the maybe-shady store. The Boss of the place picks up. The Boss says he has some cool stuff, like a collection of Blanton’s bottles with every stopper (there’s eight different bottle stoppers for Blanton’s). The Boss also has a bottle of Pappy for $800. My heart skips a beat. Progress! But then he clarifies that it’s the ten year — Old Van Winkle. Not technically Pappy, and should go for $250 or $300 at most, according to my research. Damn.

The Complete Guide to Pappy Van Winkle Bourbon Whiskey

Why Pappy’s famous, how to get it, how much you’ll have to pay & more. Read the Story

No Pappy, then? “We get some rare bottles in occasionally,” The Boss says. “I collect some cool stuff. You collect? Come in tomorrow. Don’t drive yourself. We’ll drink from my personal bar.”

I show up the next night, curious, a little excited. The store is long and narrow, with lots of neon lights, a line of fridges filled with boozy canned mixed drinks on one side and stocked liquor shelves all down the other. The Boss has got some interesting goods behind the counter. There on the top shelf is the full set of Blantons Bottles ($1500) arranged in two collector’s crates. He has a bottle of Thomas Handy ($550), both Nikka Coffeey Grain and Coffeey Malt, and a bottle of the Henry McKenna 10 year. It’s $99. “Since it won that award,” he says.

I ask how he gets the cool bottles. A lot of work, he says. “I sell a lot. Move a lot of whiskey. I get the VP of Fireball in here, other bigwigs, all the time.”

He remembers me from my phone call and asks me if I’ve heard of Weller CYPB. I have not. He got one of the twelve bottles that made it to LA, he says.

“How is it?” I ask.

“What do you mean?”

“Have you drank it?”

“No.”

He is suddenly suspicious. I try to work in the truth, like before, that I’m a journalist working on a story, but I freeze; saying that at the moment seems unwise. Instead, I tell him I’m a magazine writer and I write about bourbon, and I’m interested in finding Pappy.

I have blown it. His eyes sharpen into suspicious blades. I realize The Boss is jacked. “Do you collect or do you drink?” he asks.

“I drink, mostly,” I say. “I’m a writer. Can’t really afford to collect the expensive stuff, but I’m fascinated by it. You mostly collect then?”

He nods.

“You never drink your own bottles?”

“No, I don’t ever drink them.” Like I’m an idiot. Am I an idiot?

I play it cool and start asking him about other bottles. The Boss cools off. He pours us something from his “personal bar” that ends up being Blanton’s vodka in paper cups. (Disappointing, but free is free.) We go outside for a smoke. He leans on a blacked-out Tesla Model S — his. “Where do you do your laundry?” he asks. Points next door. “You should bring it over here. It’s my store, too.” A laundromat.

The Boss holds his paper cup of Blanton’s vodka and his cigarette and leans on the bumper and exhales slowly. “Small business is hard,” he says. I understand a bit, being a freelancer. “Yeah,” he says. “But business is — ” he looks at the two storefronts. “More than this. I can’t say more.” I nod like I understand. He smokes and we drink.

The Boss has been drinking since he was twelve, says he’s been collecting since then, too. I tell him I like to hunt the good stuff that’s also affordable — the Four Roses Small Batches of the world, maybe an interesting Japanese whisky. When I score a cheap bottle of Maker’s Mark, I call my dad and brag.

He makes a face at the Maker’s comment. “Never drank it,” he says. “My father said only to drink what you can’t afford.”

I cut to the chase. Does he ever get Pappy in — the 15, the 20, the 23?

He says he hasn’t before, but maybe he could.

I tell him someone I knew once found it for $500 bucks. I’m looking for it for that kind of price, maybe a little less. That’s a good deal, he agrees. Not something he expects to be able to do. But he can try. “How?” I ask. He won’t say much. He’d just call his guy, tell them what he wanted, and since he sells a lot, his guy would probably help him out.

“But say you were getting it for someone else,” he says, “like your friend who found it for five hundred. I could get it for you this amount, say eight hundred dollars, and then you could tell him it cost a little more. A thousand. Take care of yourself.”

I have been hunting through the middlemen of the black market whiskey world for weeks, and now, I get my first chance to become one myself. This feels like progress.

I like The Boss. We go back inside his store and he gives me mini shots of mezcal and the sweetest rum I’ve ever tasted. He means me no ill, personally. He is also a salesman and a hustler. He tries to sell me expensive gift sets of Jack Daniels and Heaven Hill. I pass, but I buy a couple cheap bottles to stock my bar, and show him I’m for real, and tell him to ask his vendor how much a bottle of Pappy’s 15 would run. Then I get the fuck out of there.

The next day, a little hung over from paper-cup vodka, I sit around and wonder why the hell people do this sort of thing. Not the rich people who want Pappy because it’s hard to get, or so they can show off. The people who really love bourbon — who enjoy learning it, knowing it, drinking it. How does hyper-expensive, impossible-to-find bourbon fit in with being a whiskey lover?

Willett’s 4-Year Rye is the most available of any Willett whiskey, and one of few expressions the brand distills and matures itself. The rest is sourced from other distillers.


I realize that, beside the challenge, I don’t know why I’m chasing the stuff so hard. I can’t collect consumable things worth a shit. My humidor holds cigars a few months before I burn them, tops. My parents once got me a bottle of Lagavulin, a $90 bottle, for Christmas. I threw a New Years Party a few days later and, blasted, poured every friend in the room three fingers until the bottle was empty. It was stupid. It was irresponsible. It was why I like drinking in the first place.

I take that bottle of Willett 4-year rye out on the porch, and I sit outside, and I taste the stuff. Slowly. It is good. So good that the burn in my esophagus is like slipping into a hot bath. So good that the traffic hissing by outside, and a cricket’s insistent chirp, and the passing of a news chopper on its way to shoot live wildfire footage, all flow together to become night music. So good that I remember why I love sipping bourbon. That like a lot of bourbon lovers, I’m just after something that tastes so good that the taste becomes a memory all its own.

The Willett cost $60. A lot for me, a broke writer who drinks casually. It is good because it is a treat, and because buying it gave me the small rush of a good find. But it is mostly good because its taste grabs ahold of my senses and sends my mind spinning, like good art should.

I call up my friend, the one who gave me Pappy at his wedding when I was too drunk to taste it. He was a collector before; that’s how he got the bottle. A guy he’d bought some nice bottles before on Craigslist gave him an especially good deal.

“But I don’t collect anymore,” he tells me. “When I first bought the bottle of Pappy that I gave you, I told myself I was buying it to drink on a special occasion. Then the wedding came around and I had to buy a second bottle before I would let myself uncork the first one. Just so I could keep it sitting there in my collection. That was pretty dark.”

He was right, it was dark. And I could picture something kind of dark now, when I thought about getting Pappy, which was often: on the vague day in November when Pappy hit liquor stores, the folks who wanted it and who had become regulars over the year would go streaming into liquor stores across the country, with a thousand dollars in their hands. Most of them wouldn’t get the chance to give their money away. A lucky few would get their bottle of Pappy, and hold it with two hands out to their car, looking over their shoulders to make sure they weren’t being followed by the covetous horde. They’d take the bottle home and put it on the shelf and stare at it lovingly. A precious few might even dare to take a few sips. How many would share it with friends, drink half of it in one night and have a really fucked up, fun time? I’d gamble to say almost none.

During my month of hunting Pappy, two things had proved impossible: First, finding a bottle for anywhere near retail price. Second, finding anyone who’d bought the stuff to drink it and actually felt good about it afterward. How many of the people who managed to buy Pappy this year, and who drank the stuff, would really enjoy it? When has anything you’ve put that much pressure on turned out to be as perfect and amazing as you’d imagined?

On the first day of November I went down to my favorite bar, where I’d seen three Pappys sitting on the shelf. The 15-year was $55 a shot, which works out to around $715 for the entire bottle. Best deal I found. But the owner wouldn’t let anyone buy it wholesale. To get the deal, you’d have to drink it down, shot by shot.

I bought two, one for the bartender, one for me. We drank them slow.

And that Pappy was good.

So good.

But it was not worth all the trouble.

The author’s view from the end of the Pappy-hunting rabbit hole.

More by Chris Wright | Follow on Twitter · Contact via Email
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