I Drank Rare, Unopened Century-Old Whiskeys. Here’s How They Tasted.

“We’re about to drink through all the world wars and the Great Depression,” Zev Glesta says, gingerly tugging on a metal tamper proof ring adhering the cap to a bottle of 1932 Old Grand Dad 16-year bourbon. The metal seal is particularly tricky and Glesta, Sotheby’s assistant vice president of whiskey for North America, jokes about perhaps needing pliers to wrestle it off. “Who knew they did such a good job at these early seals?” he says, finally freeing the cap.

For the first time in nearly 100 years, this deep-amber bourbon, distilled in 1917, meets air. Next, it meets my lips.

Its label, which reads “Unexcelled for medicinal purposes,” is lying. The liquid is excellent. With a robust nose of molasses, oak, and a hint of old cardboard, the palate picks up some sarsaparilla, a touch of soap, and a cherry cola tingle at the end of the finish. “It’s grippy and chewy,” Glesta says, adding he gets a chalky, cherry Pez note. “This is the only bottle we have, and we chose to drink it. It won’t be in the sale.”

That sale? Sotheby’s Whisky & Whiskey auction, which is live now through June 12 and features hundreds of rare and allocated bottles from the United States, Scotland, and Japan. A vintage whiskey collection spanning from Prohibition to just after World War II, amassed over decades by Mark Wade, co-founder of the Vintage Whiskey Society, is the highlight. “Mark is one of the most passionate whiskey collectors, not only because he collects the best bottles, but because he’s willing to open all of them,” says Glesta.

Proof of Wade’s benevolence is neatly arranged in front of me in a Sotheby’s conference room: seven unopened bottles of the rarest American whiskeys still in existence, poured for clients and a few select press members. The tasting flight includes a half ounce of 1934 Black Gold 20 Year Old, 1929 Dowling Bros, 1932 Old Taylor 16 Year Old, 1955 Dowling Bros Deluxe 8 Year Old, 1950 Old Grand Dad Bottled in Bond, 1940s Old Taylor Bottled in Bond, and the 1932 Old Grand Dad currently swirling inside my Glencairn glass.

“We’re about to drink through all the world wars and the Great Depression,” says Sotheby’s assistant vice president of whiskey for North America Zev Glesta.

All are 100 proof, and, except for the 1932 OGD, bottles of each will be available in the auction, each estimated between $1,000 and $1,500—though it’s likely they’ll sell above those estimates. Also in the sale: a cadre of ultra-rare American whiskeys including a 24-year-old Stagg, a 19-year-old Stagg Special Reserve, and perhaps the most intriguing of the lot: a 16-year-old Four Roses from 1933, crafted by Albert Blanton at the George T. Stagg Distillery.

That’s part of the allure about vintage whiskey; it’s history in a bottle. Made during wars or economic turmoil, these pours come from erstwhile distilleries, whose owners and workers are now heralded as industry icons. Every sip of bottles like these erases a piece of the past. What remains is coveted. Not just for the flavor, but for the chance to hold a time capsule.

About that flavor, though. Vintage whiskey doesn’t shout like today’s bourbons and ryes. It murmurs, then lingers. Modern pours lean bold, brash, and barrel proof, while vintage whiskey unfolds slowly, its quiet complexities revealed layer by layer, like patina sloughing off with time in the glass. And the longer the old stuff breathes, the further it wanders—deep, wide, and wonderfully unpredictable. The distinction is clear: modern bourbon makes an entrance, but vintage whiskey leaves an impression.

“It’s giving a note of sitting in your grandmother’s basement, with the ashtray three rooms away, and you’re eating a Snicker’s bar,”

Take the Old Taylor from the 1940s. When Glesta first opens this non-age-statement bourbon, the nose features caramel, honey, and literal dust that’s been blown off old cardboard. It’s initially light on the palate, with pops of oak, vanilla, and sweet cream, before it dries down into a rambunctious cola note, like Dr. Pepper in an old library. Revisit the liquid fifteen minutes later, and it transforms from light and floral to rubbery and medicinal with far more funk.

The 1932 Old Taylor, distilled in 1917 and bearing an age statement of “16 Summers,” begins with a minty, herbaceous note that moves into drying flowers. After ten minutes, sweetness breaks through the vegetal notes. “It’s giving a note of sitting in your grandmother’s basement, with the ashtray three rooms away, and you’re eating a Snicker’s bar,” Glesta says, musing—correctly, in my opinion.

The 1950 Old Grand-Dad four-year opens with a sharp hit of ethanol and a cool flash of mint—assertive from the jump. On the palate, it swings lush and deep, like a Luden’s cherry cough drop. Cherry, in all its moods, is a recurring note in the vintage bourbon palate. It shows up as rock candy in the 20-year Black Gold, distilled in 1914 and bottled in 1934—an absurd age statement for the time. (The name fits; it looks like motor oil.)

The Dowling Bros-distilled bourbon noses rich and saccharine, but a hint of geosmin—a damp, musty note reminiscent of wet concrete—creeps in late. The sip, however, underwhelms. It lacks the depth promised by the nose, leaning instead toward a flat, mineral finish. Glesta clocks the low fill level, chalking up the letdown to oxidation.

Every sip of bottles like these erases a piece of the past. What remains is coveted. Not just for the flavor, but for the chance to hold a time capsule.

The remaining two Dowling Bros pours duke it out in a showdown for the tasting crown. The Dowling Deluxe 8 Year, made in 1947 and bottled in 1955, is so dark it swallows light. It’s a stunner, though—rich, sweet, chewy, and deep, with an overall note of chocolate covered espresso beans. Then, there’s the thirteen-year-old 1929 Dowling Bros pint, likely the only wheated bourbon in the lineup, thanks to Arthur Phillip Stitzel, who oversaw this production just six years before co-founding the legendary Stitzel-Weller Distillery with W.L. Weller and Julian “Pappy” Van Winkle. As the cork slides free with a squeaky gasp of air, Glesta is giddy. “This is so well-preserved,” he says, beaming. “The best fresh crack you can get.”

This bourbon is the victor. The nose—umami, mushroom, honey, maple syrup, and a flambé of bananas Foster with cherries—is mirrored note for note on the palate, with a ribbon of cherry syrup riding the edges of the tongue through a lengthy finish. The final impression? That sweet, ambrosial liquid at the bottom of a fruit salad bowl. It’s so transcendent that I’d happily skip a mortgage payment to own a bottle.

In the end, though, the real flex isn’t buying a $10,000-plus bottle. Knowing its value and opening it anyway is.