Brian Mosoff didn’t want to be the center of attention, so he left his table at Sotheby’s headquarters in the Breuer Building on New York City’s Madison Avenue and drifted to the back of the auction room. As the lots rolled by, Mosoff watched quietly, still fortified by the exclusive tasting laid on to butter up bidders prior to the action.

Sensing his moment, Mosoff struck, raising paddle 2529 for the first time. Another flourish wasn’t needed. The gavel came down and Mosoff had made history—purchasing the most expensive bottle of American whiskey ever recorded: $162,500 for an Old Rip Van Winkle 20-Year-Old Single Barrel “Sam’s” bourbon.

“There was no part of me that felt, ‘What have you done?’” Mosoff, 41, tells TIME by video call from his home in New York City. “To this day, I've never had a single moment of regret.”

Mosoff’s acquisition captured the headlines but there were plenty of other stars at The Great American Whiskey Collection, which collectively raised $2.5 million on Jan. 24, doubling pre-sale predictions, making it both the world’s most valuable sale of American whiskey as well as the most valuable single-owner spirits auction ever held in New York. All 319 lots were sold.

It’s just the latest signal that American whiskey is finally emerging from the shadows. While rare bottles of scotch can easily fetch seven figures—the most expensive is a $2.7 million Macallan Adami 1926 also sold by Sotheby’s— and Japanese whisky changes hands for hundreds of thousands of dollars, American whiskey has traditionally been the poorer cousin. (Note the extra “e” in the spelling for American and Irish whiskey.) 

But as the U.S. prepares to celebrate its 250th year, Mosoff says it’s high time American whiskey got due credit for both quality and cultural significance. “American whiskey is still sometimes seen as not quite the same [as scotch],” says Mosoff. “But there are these historically important bottles and producers that have not yet made their mark on the global stage.”

It’s overdue recognition that would track the buzz around American wine, with some neat historical parallels. In 1976, in an event to mark the U.S. bicentennial, Steven Spurrier, a British wine merchant, organized a wine tasting in Paris that pitted French bottles against Californian. Spurrier, who predominantly sold French vintages, wasn’t expecting anything other than a trouncing for the parvenu.

In the end, the all-French panel ranked a Napa County wine best in both the white and red category, prompting at least one judge to withdraw her ballot in horror. What became known as the “Judgment of Paris” was the final vindication that American wine had come of age.

“Overnight, that basically changes the entire wine world,” says Mosoff. “And I think that American whiskey is at that same inflection point.”

American whiskey’s lower price point means collectors are buoyed by a nascent American whiskey boom, especially if Asian and European collectors start getting in on the action.

“Prices will continue to go up as long as prices are proportionally so much lower than other categories,” says Jonny Fowle, vice president and global head of spirits for Sotheby’s. “If you're buying bottles at $10,000, they can quite easily double in price. There's so much room for growth.”

It’s also a validation of tangible value at a time when people are increasingly digitally detached, baring their souls to AI chatbots rather than neighborhood bars, and plowing their savings into ethereal assets like Bitcoin.

“As the world is moving more digital, less connected to community, I think of spirits as bridges of cultures, humanity, that create a conversation around why things matter,” says Mosoff. “It's not just about what's in the glass and the taste. It's something deeper than that.”

He’s not alone. A 2024 report from Bank of America shows 94% of Gen Z and millennials expressed interest in collectibles, with watches, classic cars, and wine and spirits ranking highly. Notably, interest declined with age, with just 80% of Gen X and 57% of Baby Boomers captivated in the same way.

Still, there’s also a question of what vintage items will survive the test of time: does Gen Z care about Chippendale furniture or even John Lennon’s guitars as much as previous generations? Or are Mario Bros memorabilia and Pokémon cards the new cultural touchstones? (One of the latter just fetched $16.5 million at auction.

Mosoff, who was born in Toronto and has worked in everything from tech and wedding photography to asset management, says he has been down “every rabbit hole” with collecting, from wine and records to luxury watches to classic cameras, showing off a vintage Oskar Barnack and Hasselblad as well as the pink plastic Le Clic portable camera immortalized by Marisa Tomei in the 1992 comedy My Cousin Vinny starring Joe Pesci. “It is objectively low-quality garbage, but it's fun, right?” laughs Mosoff. “Not everything has to be about the dollar value.”

Mosoff says the common denominator is cultural cache. “I love stories,” he confesses. “I care about cultural preservation in modern products. It's a connection with traditions, history, people, and communities.”

When it comes to historical significance, alcohol has few peers. Imbibing has been intertwined with human civilization for millennia, with the earliest recorded vineyards dating back roughly 8,000 years in the South Caucasus region. Iran had a 5,000-year history of winemaking until the 1979 Islamic Revolution, Romans would appraise which land to conquer partly on their suitability for vines, while Carthusian monks have distilled Chartreuse for almost four centuries.

In the U.S., liquor taxes played a pivotal role in the nation’s foundation and, for better or worse, mercantile flourishing. The colonial “triangle” molasses trade dating from the 17^th to 19th centuries involved Europeans selling African slaves to sugar plantations; the molasses produced then sent to New England distilleries to make rum; and that liquor exported back to Europe.

But the end of colonial rule galvanized a new frontier spirit around booze, with Americans shunning the sherry, port, and brandy favored by the stiff Europeans, and instead leaning into their own hooch created by a mash of whatever grains were on hand. “It's Americans saying, ‘We don't want to drink sherry and scotch as we're pushing back from the Old World,’” says Mosoff.

It wasn’t necessarily a smooth transition. Following the American Revolution, the new U.S. government was so beset by war debt that Treasury Secretary Alexander Hamilton in 1791 proposed a federal excise tax on distilled spirits—the first levied by the national government on a domestic product. 

The tax sparked fierce resistance, especially among western Pennsylvania farmers, who saw it as a sign of the federal government's tyrannical bent, and organized protests that escalated into the tarring and feathering of tax collectors. President George Washington responded by mobilizing nearly 13,000 militia troops to suppress the “Whiskey Rebellion” in what was the first major domestic crisis of the new republic.

Whiskey continued to shape American society. When the Temperance Movement spurred the 18th Amendment ban of alcohol in 1920, the federal government lost one of its largest tax streams almost overnight, while opening the door for an organized crime bonanza that galvanized jazz culture in speakeasies, which helped to normalize interracial mingling, and inspired a mobster lore that still dominates popular culture today. Prohibition’s subsequent repeal was partly driven by the Great Depression changing the political calculus.

The Great American Whiskey Collection contained at least five pre-Prohibition bottles, including a George T. Stagg from 1915, when the distillery—today rebranded as Buffalo Trace—appeared destined to fold as Prohibition beckoned. Instead, the proprietor cannily finagled one of only six medicinal whiskey licenses, allowing it to survive the dry years.

It’s perhaps surprising that Mosoff’s record-breaking bottle was comparatively young, bottled nearly half a century after Congress called time on Prohibition. Still, it makes up for youth with rarity, being the highest proof Van Winkle whiskey ever produced, and one of only 60 bottles ordered especially for the legendary Sam’s Wine & Spirits in Chicago.

“It's the same with scotch whisky, where the super old stuff is not always super valuable,” says Fowle. “There's a sweet spot for whiskey collecting, which is modern enough that producers knew what they were doing, but long enough ago that these bottles are now really rare.”

The handicap American whiskey faces is strict rules about production, with both bourbon and rye requiring aging in new oak, which is a concession to the cooperage industry to keep supplying fresh barrels. While this has economic benefits to both coopers and indeed the whisky makers—which earn a secondary income selling used barrels predominantly to scotch distilleries—it limits the diversity of flavor profiles in American whiskies.

“As long as that restriction continues, it will struggle to become universally appealing,” says Fowle. “But if they can change the regulations then it could start to get a bit more interesting.”

A larger following for American whiskey might mean a tidy profit for Mosoff when, and if, he chooses to sell up. But is he not tempted to drink his record-breaking purchase? “Are you insane?” he laughs. “Zero chance.”

Mosoff pauses with the unmistakable air of impending confession. “I’ve literally never even held it,” he says finally. “I’ve only seen it behind glass. It's sort of a Smithsonian piece—you don't drink this bottle; you preserve it, you just hold it for the next generation.”