When Max Shapira decided to part with three bottles from his personal bourbon collection, he wasn't just selling whiskey. He was putting more than a century of American distilling history on the block — and doing it for charity.
Shapira, the executive chairman of Heaven Hill Distillery, has curated what's being called the Old Fitzgerald Archival Collection, a trio of bottles that trace one of America's most iconic bourbon brands from its pre-Prohibition roots all the way to the modern era. The collection goes up for auction through Sotheby's, with online bidding opening June 11 and running through noon Eastern Time on June 26, 2026.
For serious bourbon collectors, this is the kind of event that doesn't come along often. Maybe ever.
A Brand With a Story Worth Telling
Old Fitzgerald isn't just old. It's historically significant in ways that most whiskey drinkers don't fully appreciate.
The name was first trademarked in 1884, inspired by a man named John E. Fitzgerald — a treasury agent with a reputation for helping himself to whiskey from the very barrels he was supposed to be guarding. Whether that origin story makes the brand more appealing is a matter of personal taste, but it certainly gives it character.
From the beginning, Old Fitzgerald built a reputation for quality. The whiskey earned its following through sales on luxury rail cars, steamships and private clubs — not exactly the image of a workaday pour. It was the kind of bottle that ended up in the hands of people who knew the difference.
During Prohibition, Old Fitzgerald was among a small group of brands granted licenses to produce medicinal whiskey. Doctors could prescribe it. Whether it cured anything is debatable, but it kept the brand alive through one of the darkest chapters in American spirits history.
After Prohibition ended, Julian "Pappy" Van Winkle took the label and shaped it into the wheated bourbon it remains today — using wheat as the secondary grain instead of rye. That decision turned out to be defining. The Stitzel-Weller Distillery became the home of Old Fitzgerald for decades, producing whiskey that collectors still hunt for today. When Stitzel-Weller closed its doors in 1992, production moved to Bernheim Distillery, which was then owned by Diageo.
Heaven Hill acquired Bernheim and the Old Fitzgerald brand in 1999, and with that purchase came something extraordinary — 12 barrels of actual Stitzel-Weller bourbon. That stock would eventually become one of the three bottles now heading to auction.
What's Actually Being Sold
Each bottle in the collection represents a distinct moment in Old Fitzgerald's long timeline. Together, they span nearly a century of bourbon making.
The Pre-Prohibition Pint
The oldest piece in the collection is almost hard to believe exists in any condition worth bidding on.
The 1934 Old Fitzgerald 18-Year-Old Bottled-in-Bond Kentucky Straight Bourbon Whiskey was distilled and barreled in 1917 by A. PH. Stitzel — the same operation that would later become part of the legendary Stitzel-Weller Distillery. It was bottled in 1934 at 100 proof, just after Prohibition's repeal.
Think about what this bottle lived through. It was distilled at a time when many other distilleries were shutting down or pivoting their production for wartime purposes, making it one of the last whiskeys produced before Prohibition took hold. It then sat through the entire Prohibition era and came out the other side to be bottled right as America was rediscovering legal bourbon.
It's a pint — not a large format by any measure — but as a historical artifact it's difficult to put a ceiling on what it represents. This is liquid history from 1917, handled and preserved across some of the most turbulent decades in American life.
The Van Winkle Era Bottle
The middle piece of the collection brings the story forward to 1965, and gives collectors a window into what many consider the golden age of Old Fitzgerald.
The 1965 Very Xtra Old Fitzgerald 10-Year-Old Bottled-in-Bond Kentucky Straight Bourbon Whiskey was distilled and barreled in 1955 and bottled a decade later at 100 proof. What makes this one particularly interesting beyond its age is the packaging and its backstory.
This expression was bottled specifically for the Colorado Electric Co. and comes presented in a striking red box set alongside two tasting glasses. It's a corporate gift from another era, and it captures exactly what Pappy Van Winkle's vision looked like at its peak — a wheated mash bill, the Bottled-in-Bond designation that guaranteed minimum quality standards, and ten years of patient maturation in the barrel.
This is the kind of bottle that shows up in old photographs and estate sales, if it shows up at all. Finding one this well-preserved is a rarity on its own.
The Heaven Hill Bridge Bottle
The third bottle connects the Stitzel-Weller legacy directly to what Old Fitzgerald has become under Heaven Hill's ownership, and it comes with a story that bourbon enthusiasts have been following for years.
The 2015 John E. Fitzgerald Very Special Reserve 20-Year-Old Kentucky Straight Bourbon Whiskey was distilled and barreled in 1992 — the same year Stitzel-Weller closed — and bottled in 2015 at 90 proof. It came directly from those 12 barrels of Stitzel-Weller stock that Heaven Hill acquired along with Bernheim Distillery in 1999.
After two decades of maturation, the bourbon was moved temporarily to inert tanks to stop it from aging further, preserving it at exactly the right moment. Only 3,000 bottles were ever produced, each housed in a hand-crafted wood box cut with a keyhole — a deliberate nod to Old Fitzgerald's namesake, the sticky-fingered treasury agent John E. Fitzgerald.
At 90 proof, it was bottled to let the depth and complexity come through without being masked by higher alcohol. For anyone who has ever wanted to taste what Stitzel-Weller bourbon aged to its absolute peak tastes like, this is about as close as it gets in 2026.
The Charity Behind the Auction
None of the proceeds from this sale are going into anyone's pocket. Every dollar raised goes to Bernheim Forest and Arboretum, a 16,000-acre protected woodland located about 30 minutes south of Louisville.
The forest was founded in 1929 by Isaac Wolfe Bernheim — a bourbon maker — and has been a conservation landmark in Kentucky ever since. It offers 40 miles of hiking trails, educational programs, well-regarded art installations and significant plant collections. The mission is straightforward: connecting people with nature.
The connection to the Old Fitzgerald story runs deeper than just the name. Heaven Hill's Bernheim Distillery, where the brand has been produced since 1999, shares that heritage. Raising money to protect the forest through the sale of bottles tied to that same lineage is a fitting way to bring the history full circle.
Why Collectors Are Paying Attention
The global spirits market has seen some turbulence recently, but the market for rare and vintage whiskey at auction hasn't followed the same downward trend. Collectors have continued to show up and pay serious money for bottles with documented provenance and genuine historical significance.
The Old Fitzgerald Archival Collection has both. These aren't mystery bottles pulled from an anonymous cellar. They come directly from the personal archives of Heaven Hill's executive chairman, with clear documentation of what they are and where they came from.
"Each of these bottles is a snapshot of Old Fitzgerald through the ages," Shapira said. "They tell the story of a brand that has survived and thrived through every chapter of American whiskey history, of which Heaven Hill is a proud part. I'm honored to now share them in a way that will support a meaningful charitable cause."
That kind of provenance matters in this market. When a bottle can be traced directly to the collection of the person who runs the company that owns the brand, the story behind it is about as airtight as it gets.
Heaven Hill's Place in American Bourbon
It's worth stepping back and considering what kind of company is putting these bottles up for sale.
Heaven Hill was founded in Kentucky by the Shapira family in 1935 and has remained family-owned through nine decades of American whiskey history. Today, the distillery maintains more than two million barrels aging across more than 70 warehouses spread across Nelson and Jefferson Counties in Kentucky. That's a staggering inventory by any measure.
The brand portfolio includes Elijah Craig, Larceny, Evan Williams, Pikesville Rye, Rittenhouse Rye and Parker's Heritage Collection alongside Old Fitzgerald. The distillery has won Whisky Magazine's Distillery of the Year award in both 2023 and 2024, along with a long list of other industry recognitions over the past several years.
When a company with that track record decides to send bottles from its chairman's private collection to auction for charity, the bourbon world pays attention.
What the Auction Means for the Broader Market
The Sotheby's Whisky & Whiskey sale that will carry these bottles is part of a broader online format that makes high-end auction participation more accessible than the traditional in-person model. Bidding opens June 11 and closes at noon Eastern on June 26 through the Sotheby's website, which means anyone with an internet connection and serious interest can register and participate without traveling to a major auction house.
For those who want a piece of Old Fitzgerald history but aren't in the market for a five- or six-figure bottle, the brand does have accessible options. Old Fitzgerald Bottled-in-Bond 7-Year-Old Kentucky Straight Bourbon Whiskey is available as a year-round offering and recently earned a Gold medal at the 2025 San Francisco World Spirits Competition. The seasonal Decanter Series is released twice per year and gives collectors something to look forward to on a regular basis.
But the Archival Collection is a completely different category. A 1917 distillate. A Pappy Van Winkle-era corporate bottling. The final expression from twelve barrels of Stitzel-Weller stock. These bottles represent chapters of American bourbon history that most collectors will never get another shot at.
The auction runs through June 26. How the bidding unfolds will be worth watching — not just for what these bottles fetch, but for what it says about how seriously the market values bourbon's living history.
