And the story behind them is as good as what's in the bottle
There are bourbon auctions, and then there are moments in bourbon history. What Chicago-based Unicorn Auctions is putting on the block between April 19 and 26 falls squarely into the second category — a collection that doesn't just represent serious money, but a specific, largely forgotten chapter of American whiskey culture that unfolded in the bars and liquor stores of Chicago in the early 2000s.
The headline lot is known among collectors simply as the "Binny's 18" — a Van Winkle bourbon that has already made auction history once before. When it appeared on Unicorn in 2024, it became what many in the hobby consider one of the most significant Van Winkle bottles ever to cross an auction block anywhere in the world. It sold for $86,000. Now it's back, carrying an estimate of $60,000 to $80,000, and it is once again expected to draw serious attention from collectors across the country.
The bottle is widely considered one of the five most sought-after bourbon bottles ever produced — full stop. Not just among Van Winkle releases, not just among private barrel picks, but among any bourbon ever bottled by anyone, anywhere.
You can see the entire auction here.
What Made Chicago Ground Zero for Private Van Winkle Bottlings
To understand why these bottles matter so much, you have to go back to a very specific window of time when Julian Van Winkle III was still willing to work with private accounts — bars and retailers who could select a single barrel and bottle it under their own label. It was an era that produced some of the most extraordinary and irreplaceable American whiskey ever made, and Chicago happened to be at the center of it.
Several of the most valuable private-barrel Van Winkle bottlings in history were done for Chicago establishments in those early 2000s years. The people running those bars and shops had both the taste and the access to pull off something that would later become essentially impossible. As the Van Winkle brand grew into what it is today — a cultural phenomenon with waitlists, lottery systems, and secondary market prices that make most Scotch collectors wince — those early private picks became relics. One-of-a-kind artifacts from a time that is simply gone.
The Binny's 18 is the crown jewel of that era. Binny's Beverage Depot, the Chicago-area retail institution, secured a barrel at 18 years old when most buyers today would consider themselves lucky to find a standard Pappy 15 at retail. The bottle that resulted is, by collector consensus, something that simply could not happen now under any circumstances.
The Twisted Spoke Bottle and a Bar That Deserved Better
Sitting just below the headline lot in this auction is another piece of Chicago bourbon history that hits differently — not just because of what's in the bottle, but because of where it came from and what that place meant to people.
The Twisted Spoke 16 Year Bourbon is a Van Winkle private barrel selection bottled for the Twisted Spoke, a bar on Chicago's near west side that ran for 30 years before closing permanently last year. For three decades, the Twisted Spoke was the kind of place that doesn't exist much anymore — a bar with a genuine identity, a loyal crowd, and enough credibility in the whiskey world that Van Winkle would bottle something exclusively for them. The auction estimate for this lot sits at $15,000 to $17,500.
There is a particular kind of weight that comes with a bottle like this. The bar is gone. The era that produced the bourbon is gone. What remains is a sealed artifact from a moment when a beloved Chicago institution was still very much alive and operating at the highest level. For anyone who drank there over those 30 years, this bottle is not just a collectible. It's a time capsule.
The Rarest of the Rare: Details That Make Collectors Stop Cold
Beyond the two Chicago-provenance headline lots, this auction contains several other bottles that are significant in their own right — and in some cases, genuinely singular.
One lot is described as one of only three known Pappy Van Winkle 23 Year private barrel picks ever bottled. The Pappy 23 is already the rarest expression in regular Van Winkle production. The idea that a private barrel pick was done at that age — and that only three examples of it are known to exist — puts this in a category of scarcity that most collectors will never encounter again.
Another lot represents something even more specific in its rarity: the only Van Winkle private bottling ever done at exactly 16 years old and 105 proof. In a hobby that often trades in degrees of rarity, this is an absolute. There is no other bottle that fits that description. There never will be.
The collection also includes one of the few fully custom private-label bourbons ever bottled by Willett — a distillery with its own deep history and collector following. Willett private label work from this era is scarce by any measure, and the examples that do surface tend to move quickly and at serious prices.
What It Means When Bourbon Becomes a Cultural Artifact
Unicorn CEO and co-founder Phil Mikhaylov has described these bottles as cultural artifacts as much as collectibles, and that framing is worth sitting with. There is a difference between a rare bottle that is simply hard to find and a rare bottle that carries a story — a specific time, a specific place, specific people who made decisions that now look prescient.
The Chicago Van Winkle picks of the early 2000s are the latter. They document a moment in American whiskey history when the bourbon revival was still building momentum, when Julian Van Winkle was still accessible to the right buyers, and when a handful of Chicago bars and retailers had both the vision and the relationships to do something that would become historically significant. Nobody was thinking about auction records in those years. They were just buying good whiskey for their customers.
That's part of what makes these bottles so compelling. They were not created for speculation. They were created to be poured and enjoyed in a bar or sold to customers who wanted something special. The fact that they have survived sealed and intact long enough to appear in a serious auction house speaks to both the care of their owners and the depth of what the American whiskey market has become.
What This Auction Actually Represents
Taken together, the collection Unicorn is presenting this week is not simply a list of expensive bottles. It is a portrait of a city's relationship with bourbon at a very specific moment in time — a moment that shaped what these products are worth today, culturally and financially.
For collectors who have spent years tracking down significant American whiskey, this auction represents a rare convergence of provenance, scarcity, and historical documentation. The bottles can be verified. Their origins are known. Their significance is established.
For anyone else paying attention to where American whiskey has been and where it is going, this auction is a reminder that the history of bourbon is not just a story about Kentucky. Chicago had its moment, and these bottles are what that moment left behind.
The auction runs through April 26 on Unicorn's platform. The estimate on the Binny's 18 alone — $60,000 to $80,000 — signals that the market for historically significant American whiskey shows no signs of cooling off.
