This Guy Has Every Whiskey Lover’s Dream Job: Hunting Down the Rarest Bottles on Earth

When Zev Glesta was a bartender, the priciest bottles of whiskey he would handle might be a 23-year-old Pappy Van Winkle or a 25-year-old Michter’s. Today, that would count as a dull day. 

Glesta is a whiskey specialist at the New York location of Sotheby’s. He is the first person to hold that position in the North American jurisdiction of the global auction powerhouse. Every day, he now handles unicorn bottles that even the most ardent aficionados of vintage whiskey might see only once or twice in a lifetime, if that. 

But the 350-bottle so-called Great American Whiskey Collection that sold at Sotheby’s in January took his job to a new level. It was the most valuable single-owner collection of American whiskey ever to come up for auction and included several bottles of Stitzel-Weller private stock bottles from the Berghoff restaurant in Chicago, four bottles of fabled Red Hook Rye, and lots of Very Old Fitzgerald. It realized $2.5 million in sales.

Not a bad day’s work for a former drink slinger. 

“The learning curve was just being blown away every day,” said Glesta of his job. “You have to get over the fact that you’re saying ‘we’re not worthy’ all the time, because it is the craziest whiskey.”

Glesta was born in Brooklyn and partly raised in Australia. Similarly, his career in hospitality has been divided between New York, where he worked at the Danny Meyer restaurants North Side Grill and The Modern, and Melbourne, where his credits included Fat Duck and Dinner by Heston Blumenthal. He first heard of the opening at Sotheby’s from a former Modern colleague who had been hired there as a wine specialist. He leapt at the chance.

“The name Sotheby’s really carries an enormous amount of value,” he said. After six interviews, he landed the job. Sotheby’s already had spirit specialists in its ranks, but none based in the U.S., where interest in vintage spirits has boomed in recent years.

“Everyone was getting into hobbies, and half of Americans somehow took up whiskey at that moment,” said Glesta. “Sotheby’s needed someone in America, and I was that American.”

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The first thing he worked on was the “Three Continents Collection” auction in 2021. It included nearly 5,000 whiskeys from Scotland, Japan and the U.S. that were put together by a single owner. It included a full contingent of The Macallan Lalique Six Pillars Collection, a series of bottlings the Scotch collaborated on with the renowned French crystal maker.

Not every bottle Glesta handles contains whiskey. In early 2025, Sotheby’s auctioned off two cases of an obscure product called Chandler’s Gin, distilled by the Stewart Distilling Co. of Philadelphia sometime around 1909. That lot took a bit of digging regarding its origins.

“The most important thing was saying, ‘I don’t know,’ and finding someone who does know,” said Glesta of his early days on the job. “You can’t take a leap of faith with authenticity.”

At first glance, the idea of a bartender taking on the mantle of a Sotheby’s expert seems a bit improbable. But Glesta believes his previous resume primed him well for his new career. 

“I’m a little bit more geared towards sales,” he said. “I’m hospitality forward. I can chat the chat. I hold hands, so to speak. I think being from a sales position, in an environment under stress, is very helpful here.”

When we spoke, Glesta was preparing to inspect 330 bottles of incredible single malt Scotch. He was also expecting a collection of ten one-gallon bottles of vintage American whiskey, including some Old Fitzgerald bottled-in-bond, Weller from the 1960s, 100-proof Old Grand Dad from the early 1970s, and—most exciting—a two-gallon glass carboy of Prohibition-era medicinal rye. “I’m so excited to see it tomorrow, I can’t wait,” he said.

These days, with a few years at Sotheby’s under his belt, Glesta doesn’t say, “I don’t know” as often as he once did. He can eyeball a group of bottles and guess at what they might fetch on the auction block. 

“It is quite cool to look up and down a collection and say, ‘yup, that’s $100,000,’” said Glesta.