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Artwork for “Pappy Van Winkle”

Episode 3

Pappy Van Winkle

· 8 min

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Show notes

This week we uncork the white whale itself: Pappy Van Winkle. We give the bourbon its due — a sumptuously soft, wheated pour of caramel, dark fruit, toffee, and polished oak that genuinely deserves its halo. Then we turn our attention to the man who "owns" it: the allocated-bottle obsessive in the fleece vest, staking out liquor stores at dawn, photographing sealed bottles on reclaimed barn wood and captioning them "Grateful," while saving the actual whiskey for an occasion that, by design, will never arrive. A loving roast of the collector who confused scarcity with quality and the hunt with the having. Tasting notes and character flaws, as always.

The tasting card

Bourbon

Pappy Van Winkle's Family Reserve

45.2% ABV · 10–23 years (varies by expression) · Buffalo Trace Distillery

91/ 100 proof
Nose
Warm caramel, vanilla bean, and brown sugar, with dried cherry, pipe tobacco, and old leather underneath.
Palate
Staggeringly soft — toffee, butterscotch, dark fruit, and a late, polite wave of baking spice.
Finish
Long and warming, with caramelized sugar and a last curl of oak char.
“A genuinely excellent wheated bourbon — and nowhere near forty times better than the pour gathering dust beside it. The whiskey earns its halo; the secondary-market sermon does not.”

Get past the mythology and what’s actually in the glass is soft — almost an apology. This is a wheated bourbon, so the rye spice that usually bites has been quietly escorted out and replaced with caramel, vanilla, and brown sugar, a swell of dark fruit, a finish that goes long and warm and gently sweet. It is genuinely excellent. It is also not four hundred — or four thousand — dollars better than a wheated pour at one-fortieth the price. The whiskey never asked to be a trophy.

Which brings us to the man who made it one. Call him Grayson Wexley: a “collector,” in the same tone other men say “sommelier” or “survivor.” He doesn’t have a palate, he has a wishlist. He stakes out strip-mall liquor stores at 7:40 on a Tuesday, he photographs the sealed bottle on a slab of reclaimed barn wood, he captions it “Grateful,” and he never breaks the wax — because he’s “saving it for a special occasion” that, by design, can never be special enough to justify the lost resale value. The Trophy Hunter doesn’t drink Pappy. He has almost-drunk it, forever, in front of an audience.

Here’s the affectionate part, because there’s always one: the hunt is real joy for him, and the bottle he’s guarding really is lovely. He’s just standing in the doorway of something warm and generous and refusing to walk through. Pour two fingers of whatever wheated bourbon you can actually afford, and drink it — on a Tuesday, for no reason at all. That was always the special occasion.

  • special occasion
  • would re-pour

The drinker we imagined

The Trophy Hunter

Loves the chase more than the pour — and the receipt most of all.