Who Sells The World's Most Expensive Bourbon?

What's the most you'd ever pay for a bottle of rare bourbon? If you're anything like collector Brian Mosoff, you'd pay $162,500. Mosoff shelled out this figure after placing the winning bid on a bottle of Old Rip Van Winkle 20 Year Old Single Barrel "Sam's" bourbon at a Sotheby's auction in January of 2026, making it the most expensive bourbon sale to date. Only 60 of these bottles were produced back in 2003, specifically for Sam's Wines & Spirits, a now-defunct liquor store in Chicago. In fact, it's been over a decade since a "Sam's" bottle was seen at auction at all.

For fine spirits collectors in the know, it's unsurprising that the title of most expensive bourbon went to a Van Winkle. Since the 1890s, the Van Winkles have had a hand in making wheated bourbon  and built their reputation at the Stitzel-Weller Distillery and, more recently, at the Buffalo Trace Distillery in Frankfort, Kentucky. Demand for Old Rip Van Winkle is sky-high due to its impeccable quality and scarcity. According to Sazerac, the brand has racked up over 41 tasting awards since 2009. Julian P. Van Winkle III, President of the Old Rip Van Winkle Distillery, told Garden and Gun in 2012 that the 6,000 to 7,000 cases the distillery releases annually total "about what Jim Beam puts out in ten minutes."

As you can imagine, purchasing a bottle of Old Rip Van Winkle 20 Year Old Single Barrel "Sam's," distilled in 1982, is next to impossible. Like bid winner Brian Mosoff, you're only likely to encounter one at a rare spirits auction. You might get lucky finding a unique bottle in specialty online shops that buy and sell rare bourbons, but seeing as even modern Van Winkle releases have a waiting list, you'd be hard-pressed to spot something as ultra-rare as the 20 Year Old Single Barrel "Sam's.

Determining the prized bourbon's tasting notes (one of the ways experts pick a good bourbon) isn't easy information to come by. Since only 60 bottles were made, owners hold onto them to increase their value. Mosoff stated to Time's Carlie Campbell that he won't be drinking — or even touching — his, preferring to keep it behind glass like a museum piece. In a 2003 post on the forum Straight Bourbon, a commenter described enjoying a glass of the future most expensive bourbon ever sold. "The nose is so sweet, spicy and round ... However, on the palate, the alcohol burn becomes noticeable," they recounted.

The most expensive bourbon ever sold at auction wasn't the only Van Winkle to pull six figures. A 2007 Old Rip Van Winkle "Van Winkle Selection" from the Kentucky Bourbon Festival Master Distiller's Auction sold for $125,000, while a bottle of Very Very Old Fitzgerald "Blackhawk" 18-Year-Old from 1950 commanded $112,500. Still, neither price comes close to what Van Winkle achieved with the "Sam's" bourbon.