In the booze-buying game we call them "honey holes." Off-the-beaten-path liquor stores that seemingly no one knows about, which inexplicably have a great selection of liquid rarities. Every time you pop in there's some Japanese whisky or an oddball scotch or some vintage "dusty" bourbon that's been around since the Clinton administration. One thing that honey holes never ever have, however? Pappy Van Winkle.
Why is Pappy so rare?
First released as a 20 Year Old bourbon in 1994, Pappy Van Winkle's Family Reserve (also available in 15 and 23 year expressions) has become a sensation only in the past decade. One of the first extra-aged and "premium" bourbons to hit the market, the sweet and smooth wheated whiskey was feted early on by people like Anthony Bourdain. It appeared in movies like Crazy Stupid Love and TV shows like Justified, and eventually became impossible to find.
Where to look for Pappy Van Winkle
Still, Buffalo Trace, the distiller of Pappy Van Winkle, produces tens of thousands of new bottles every single year, which are usually released nationwide every November. Pappy is no unicorn and bottles must be lingering somewhere. But, let me just say this: you are never going to simply walk into a liquor store, "get lucky," and find some Pappy sitting on the shelves for 90 bucks. Not gonna happen.
You're going to need to know other places to look.
The secondary online market
Expect to pay: $1000–$2000 a bottle
Most people not "in the know" have never even seen a bottle of Pappy because bottles of Pappy simply don't make it into the public anymore. Instead, most bottles are sold on semi-illicit grey markets which mostly exist online via private groups on places like Facebook. The positive about these groups—assuming you can find one and get into one—is that the transaction is fairly frictionless. If you have the ability to pay the current market price for Pappy (around $1000 for the 15 Year and up to $2000 for the 23 Year), you can probably find someone to sell you a bottle. The negative, of course, is you're illegally buying booze over the internet from a stranger for a lot of money.
A control state lottery
Expect to pay: $120–$300 a bottle
Believe it or not, liquor stores in certain states are controlled by the government. In places like New Hampshire, Pennsylvania, and fifteen other states, the government has total authority over your gin, wine, Fireball, cupcake-flavored vodka, and everything else—including Pappy. In a way, however, that's a good thing. States aren't in the business of jacking up the manufacturers' suggested retail prices, nor are they in the business of playing favorites with customers. Instead, many states like Idaho and Virginia hold lotteries for the right to buy their most prized bottles like Pappy. Depending on the state's population, that could be anywhere from dozens to hundreds of bottles per year. The biggest secret is you don't have to be a state resident to enter many of these lotteries (you will, however, have to go to that state to grab your bottle should you actually win).
Your local liquor store
Expect to pay: $120-$300 a bottle
This one is most certainly not a "Get Pappy quick" scheme—but it ultimately might be the best scheme. So you have your local liquor store, right? Where you buy your monthly bottle of Hendrick's and wine every Friday night? You need to start going there more often, buying more stuff, and chatting up the store's owner and/or spirits buyer even more than you already do. And one day, after you've spent thousands of dollars, after you've become friends with that guy or gal, only then are you to start inquiring about their "allocated" bottles. Most liquor stores that get bottles of Pappy never even put it on the shelves, instead earmarking bottles for their top customers and friends of the store. That could be you (by 2021 or so if you're lucky)!
A good bar
Expect to pay: $50-$200 per ounce
The fact of the matter is: you don't really need a bottle of Pappy. Especially if you've never tried it before. Why not simply treat yourself to a glass? That's going to be a whole lot more enjoyable, economical, and feasible if you're new to the bourbon game and lack contacts and/or the courage to illicitly buy online. Go to the best whiskey bar around you, or the swankest lounge in town, or maybe just a baller steakhouse, and there's a good chance they'll have a bottle of one of the Pappys. (This blogger has attempted to list every bar in America that has it.) It certainly won't be cheap to get an ounce or two, but it'll be cheaper and easier than accessing a whole bottle. The only problem will be . . . what if you truly love it?