L ast January, a bottle of 20-year-old Old Rip Van Winkle bourbon sold for $162,500 at Sotheby’s in New York, setting an auction record for American whiskey. Distilled in 1982, it was bottled in 2003 from a single barrel selected for Sam’s Wine & Spirits in Chicago. Only 60 bottles were produced, and Sam’s originally sold them for about $100 each.
That Old Rip Van Winkle was the star of the Great American Whiskey Collection, the most valuable single-owner collection of American whiskey ever sold at auction. Its 319 lots fetched $2.5 million, well above the presale estimate—a sign that, while Scotch has had a mature secondary market for decades, American whiskey, comparatively new to the auction arena, might finally be catching up.
Eight months later, Sotheby’s offered another remarkable cache: the 328-bottle Wax Top Collection, which included the largest group of whiskeys ever auctioned together from Willett Family Estate, a family-run distiller and bottler with a devoted following.
At both sales, many of the most coveted whiskeys were single-barrel releases for liquor stores, restaurants, bars and other private clients, limited bottlings from barrels often selected by the buyers themselves. These one-off releases emerged during a period when American whiskey was struggling, an industry downturn before the 21st-century boom sent demand through the roof. They were intended for pouring, not hoarding as investments, and were originally priced to sell. “People were buying to drink, to enjoy with friends,” says Ryan Maloney, third-generation operator of Julio’s Liquors, west of Boston, who has been picking barrels for his shop since the early 2000s. Decades later, the people and places behind those types of barrel selections have become an important part of their story and appeal to collectors.
“We may see a new record for the most valuable bottle of American whiskey ever sold.”
“Doing barrel picks for liquor stores was just another way to generate income and keep the lights on,” says Jonny Fowle, Global Head of Whisky & Spirits at Sotheby’s. “It’s interesting that these came about out of necessity to keep the business afloat, and they’ve since become legendary.”
Today, American whiskey sales are slowing again, but the rarest single-barrel picks still command extraordinary prices. “We’ve certainly seen a bit of oscillation recently, but generally the rare bottles still do really well,” says Fowle. “I do anticipate that, maybe not this year, perhaps in 2027, we may see a new record for the most valuable bottle of American whiskey ever sold.”
At last September’s Sotheby’s auction, Willett performed well, including bottles of The Iron Fist and The Velvet Glove, two of their most sought-after single-barrel ryes, from 23-year-old casks selected by Bill Thomas for Bourbon DC, his first Washington, D.C., whiskey bar. Thomas, among the first bar owners in the country to select Willett barrels on-site in Kentucky, once poured Iron Fist for $18 an ounce. At Sotheby’s, it sold for $17,500. “None of us thought we were going to make a million bucks holding these barrels or selling them; we all just wanted the best whiskey,” he recalls.
The Willett barrel program began in 2004, but putting customers’ names on whiskey bottles was nothing new. After World War II, distillers supplied custom bottlings to restaurants, private clubs and even airlines. Stitzel-Weller, the Louisville distillery founded by Julian “Pappy” Van Winkle Sr. in 1935, produced private-label whiskey for favored customers through the ’50s and ’60s.
“Distillers did it for all types of companies,” says Noah Rothbaum, author of “The Whiskey Bible.” “It was cool for the restaurant or bar to have its name on the label.” A bespoke bottling, though, didn’t necessarily mean the whiskey came from a single-barrel pick. That level of hands-on customization became more widespread later, after the whiskey business hit rock bottom.
American whiskey has had its ups and downs since Prohibition. Sales began a steady decline in the 1970s and continued to fall through the early 2000s as American drinkers embraced lighter spirits like vodka and gin. Distillers, stuck with more aging whiskey than they could sell, sought novel ways to move product. Individual barrels offered bars and retailers good value and a unique product for their customers, while clearing distillers’ inventory. “Part of the reason they’re sought after now is that many of them were consumed,” says Rothbaum of those bottles. “Nobody realized there was something special.”
Few worked the single-barrel trade quite like the Van Winkle family. Pappy’s son, Julian Jr., sold Stitzel-Weller in 1972, retaining rights to a single brand, Old Rip Van Winkle—buying back barrels from the new owners. Then, in 1994, Julian Jr.’s son, Julian III, launched a new brand, Pappy Van Winkle, which would eventually become the most prized American whiskey. But it was a hard sell at first.
In the early 2000s, Maloney bought barrels of 15-year-old Pappy Van Winkle at a discount for Julio’s. He priced the bottles at $65 on the shelf. I remember a customer saying to me, ‘$65 for a bottle of bourbon? You’re crazy.’ Well, I would love to have all those bottles back right now,” he says. A similar Julio’s barrel pick from that era recently appeared on the secondary market online, with an asking price of $34,999.
“I think in the past, quality was a big driver of price,” says Fowle. “As the market matures, ironically, quality seems to become less of an issue … brand strength tends to prevail over all else.”
Nearly all the top lots in Sotheby’s record-breaking January sale trace their lineage to the Van Winkles—including the Very Very Old Fitzgerald “Blackhawk” 18, produced by Stitzel-Weller, privately bottled for the Wirtz family, owners of the Chicago Blackhawks and among the country’s largest liquor distributors, and originally intended for gifting ($112,000), and an 18-year-old Van Winkle Family Reserve, custom-bottled for New York’s Park Avenue Liquor Shop ($62,500). The Willett family’s whiskeys, though, weren’t far behind.
“You literally walked into the warehouse, cracking barrels and trying anything you wanted. There was nothing off-limits.”
Willett’s appeal to collectors complicates the single-barrel picture. While the oldest whiskeys fetch the highest prices, their production histories are often shrouded in mystery. Lambert Willett and his son Thompson launched the family distillery in 1936. When demand cratered in the 1970s, the distillery switched to producing ethanol before shutting down entirely. In the 1980s, under Thompson’s daughter, Martha, and her husband, Even Kulsveen, the business began bottling surplus casks purchased from other distillers. In 2004, after customers began asking to buy entire barrels, their son, Drew, launched a new label, Willett Family Estate, to bottle the best of their stock. Buyers learned the age statement but rarely the provenance of their barrel selection.
Bill Thomas arrived not long after the new label launched. “You literally walked into the warehouse, cracking barrels and trying anything you wanted,” he says. “There was nothing off-limits.” Those early visits gave rise to The Iron Fist and The Velvet Glove. Willett resumed distilling its own whiskey in 2012.
For legal reasons, the auction market for American whiskey took years to take shape as states that once outlawed secondary market sales began easing their regulations. Illinois authorized spirit auctions in 1993. New York followed 14 years later. Sotheby’s held its first single-owner American whiskey sale in 2021. “If you had a case of whiskey, you’d either have to send it to Europe, or maybe there was an auction house in Chicago,” says Rothbaum. “It was like the cart before the horse. We don’t want to auction these off until there’s a market—but how can there be a market if nobody can buy or sell these things?”
Until recently, most vintage bottles of bourbon and rye changed hands privately, off the books, through backroom deals and Facebook groups. “Most of the trading was done behind closed doors,” says Fowle. Now that there’s a legitimate market, enthusiasts who bought single-barrel whiskey cheap at release, set aside a bottle or two and drank the rest are starting to sell. “The guys from my generation who are retiring, or thinking about buying a summer home, or putting your kids through college—they’re starting to free up some of these bottles,” says Thomas, 56, with a laugh. “And then you’ll see it again in about 18 years, when we’re dying, and our collections are being auctioned off.”
