Stolen Spirits: The Bourbon Heist That Became a Legend

The cases were there—until they weren’t. One morning, a routine inventory check at a storied Kentucky distillery turned into the discovery of a heist that no one saw coming. The missing bourbon wasn’t just any whiskey; it was THE bourbon, the kind collectors whisper about and connoisseurs hunt for. How could so much of it vanish without a trace? Was it an inside job, a well-planned heist, or something even more sinister? As investigators dug deeper, they uncovered a tangled web of deception, underground deals, and a black-market bourbon trade that had been hiding in plain sight.

What started as a quiet theft quickly spiraled into one of the most notorious whiskey crimes in modern history. Rumors swirled through Kentucky hollers and high-end bars alike, as bottles from the stolen stash began to surface in the most unexpected places. Law enforcement, whiskey insiders, and bourbon lovers around the world were drawn into the mystery, each piece of the puzzle leading to more questions than answers. News reports circled the globe. Was it greed, revenge, or something far more personal? The truth behind the missing barrels would shake the bourbon world to its core. 

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Transcript

Since the dawn of time, the urge to take what doesn’t belong to us has whispered it's temptation into the hearts of humankind. In ancient marketplaces, beneath the awnings of spice merchants, jewelers, and fruit carts, fingers itched for unguarded treasures. Today, in modern cities and small towns alike, the same impulse lingers, as it is fueled by desperation, greed, or a fleeting moment of opportunity.

Let’s be honest — at some point, most of us have felt that tug of temptation. Perhaps it was a pack of gum when no one was looking, a stolen kiss when the invitation wasn’t clear, or even the subtle glance to a neighbors paper for the answer on a classroom test. Big or small, theft has a way of wearing many disguises.

I remember one of my own brushes with this temptation . I must have been four or five years old, trailing behind my mother at the store when a toy caught my eye. I played with it while she browsed the shelves, and without a second thought, I slipped it into my pocket. I wasn’t scheming — I was a kid who liked something and wanted it, so I took it. It wasn’t until my mother woke me from my nap at home and asked what was in my pocket that reality came crashing in. And let me tell you, her look of disappointment burned hotter than her anger. She called the store manager and made me apologize on the spot, then marched me back to the store the next day to return the toy with a second apology. Lesson learned: taking something that isn’t yours comes with a cost.

But what happens when the stakes are much higher?

Today, we explore a theft, heist if you will,  that shook the bourbon world to its core. It’s a story that countless guests on the trail ask me to unravel as they have only heard a piece of the tale or they do not completely understand why this particular theft has reached almost mythical heights, the who’s the why’s — a mystery of temptation, of betrayal, and obsession. Today’s LEGEND is the tale of the Pappy Van Winkle heist from the Buffalo Trace Distillery. A theft of such magnitude that it left its mark on history. Because, you see, every act of theft — no matter the scale — is more than a crime, they all have a story behind the act.  And some are so grand, that legends are created, both for the thief and for the stolen item.

With that, let’s get into the LEGEND of Pappygate!

Intro

In October of 2015, the quiet hum of bourbon production at the Buffalo Trace Distillery in Frankfort, Kentucky, was shattered by a revelation that would ripple far beyond its rickhouses. This legendary distillery, owned today by the New Orleans-based company Sazerac, who also owns Barton distillery in Bardstown KY, reported that more than 200 bottles of Pappy Van Winkle bourbon — valued at approximately $26,000 retail at the time (a fraction of what it would get on the secondary market) — had vanished.

Enter Sheriff Pat Melton who didn’t mince words. He labeled the event a heist and declared that the stolen bourbon was none other than the (quote) “Mac Daddy” of whiskey. That declaration ignited a media firestorm. The story broke not just here in the state, and not just across the US.  This theft was televised all over the world, that is the extent of Pappy Van Winkle’s reputation, with word spreading fast, leaping from bourbon bars in Louisville to the far corners of the world. Whiskey lovers, collectors, and opportunists alike wondered if one day they might stumble upon one of the elusive stolen bottles — liquid gold, whisked away now into legend.

Now before diving into the intricacies of the case — how it unfolded, who was behind it, and how it all came to light — it’s worth pausing for a moment. Because unless you understand just why this bourbon commands such devotion, you might miss the gravity of the crime. Most thefts come and go without more than a passing headline. This particular theft however, sparked a global frenzy. Why? What makes Pappy Van Winkle so coveted that its disappearance could stir both bourbon circles and media outlets into a swirling, relentless storm? Let’s take a moment to savor the legend behind the label — before we unseal the mystery behind its theft.

If you want a deeper dive, a two-finger pour if you will,  into the origins of Pappy Van Winkle Family Reserve bourbon, check out Season 1, Episode 6, The White Whale of Bourbon. There, I explore the men and moments responsible for creating one of the most coveted labels in whiskey history. But for now, here’s the 1 finger pour:

Julian “Pappy” Van Winkle, a legend in his own right, presided over Stitzel-Weller Distillery, one of bourbon’s most storied institutions. Stitzel-Weller didn’t just make bourbon — it crafted the best of the best. What set it apart was its wheated mashbill. Unlike most bourbons made with corn, rye, and barley, Stitzel-Weller swapped out the rye for wheat, creating a softer, sweeter profile that would later become a hallmark of greatness.

When the bourbon demand dried up in the 1970s, Stitzel-Weller shuttered its doors, and barrels of aging bourbon sat abandoned in its rickhouses, quietly gaining age, character — and legend. Years later, Pappy’s grandson, Julian Van Winkle III, teamed up with Gordy Hue to revive the family name, launching this soon to be renowned Van Winkle label. It wasn’t just the bourbon’s rich flavor and long-aging pedigree that drew attention — it was also a masterclass in storytelling and marketing. The result? A bourbon whose allure spread faster than a pile of leaves in a hurricane , quickly cementing its status as the bottle of bottles.

When Julian III partnered with Sazerac and Buffalo Trace to meet the skyrocketing demand, a new challenge arose: TIME. Bourbon, after all, doesn’t care how much the market wants it and with this label demands it. It cares only for patience. Van Winkle Family Reserve’s lineup of 10-, 12-, 15-, 20-, and 23-year-old bourbons presented an impossible riddle. Production had dwindled for decades as bourbon languished in obscurity during the 1980s and ’90s. Even if they ramped up distilling, they couldn’t speed up aging. And when you factor in the angel’s share — which is the bourbon lost to evaporation each year — the math grows even bleaker. The first year alone, as it sits in the barrel, the angels share claims 10 to 12 percent of the barrel and every year after another 4-7%.  After 20 years, what’s left of a once-robust 53-gallon barrel might be just five or six precious gallons.

Now layer on a multitude of accolades and awards from whiskey experts. Add a splash of Hollywood cameo appearances in TV and Movies, a nod from pop culture, and the intoxicating allure of scarcity. What you get is Pappy-mania — a frenzy where supply is measured in drops, demand is measured in rivers, and prices……. in gold.

So when news broke that more than 200 bottles of Pappy Van Winkle had vanished from Buffalo Trace, it didn’t just ruffle feathers. It sent shockwaves through bourbon country.

For Kentuckians, whose hearts swell with pride at producing a little more than 95% of the world’s bourbon, this was more than a crime. It was like waking up on the day of the Kentucky Derby to find an undefeated, Kentucky born thoroughbred stolen from its stall. A story too rich to ignore. A mystery too tantalizing to resist. The eyes of the bourbon world were fixed on KY’s state capitol….Frankfort, home of Buffalo Trace

When word of the missing Pappy Van Winkle hit the press, it landed squarely on media loving Sheriff Pat Melton’s radar. But tracking down more than 200 bottles of stolen bourbon at a distillery with lax security and nearly 300 employees was a formidable challenge. The trail was cold from the start, and had little to go on but empty shelves and a swirling media frenzy. Still, Melton remained determined and told everyone that he would get his man.

He had a hunch that it was an inside job. One hundred and ten employee interviews later, however, the investigation had not budged an inch. The silence was deafening. With desperation creeping in, as he knew the world had its eyes on his investigation, Sheriff Melton offered a $10,000 reward for information leading to the thieves. Calls then started pouring in — each tip raising hopes…. before collapsing into dead ends.

Then in March 2015, almost a year and a half later, a text came into the tip line.      

This was the tip Melton had been waiting for. The tipster reported a strong scent of bourbon — the unmistakable angel’s share — wafting from a property belonging to a man named Toby Curtsinger. Sheriff Melton’s pulse quickened at the name, though he couldn’t immediately place why. A nagging intuition drove him back to his investigation notes. There, buried among the names of Buffalo Trace employees, it jumped out at him: Gilbert “Toby” Curtsinger. His instincts tingled with the feeling that this wasn’t coincidence.

Armed with a warrant, Melton dispatched his deputies to search Curtsinger’s property. They found little at first as they moved along his property. Then, as the wind shifted, a rich bourbon aroma punched them in the face like a two-by-four. Beneath a tarp, they uncovered five barrels. But all the markings had been covered with paint or scratched away.or removed.  Later they were found to be barrels from the Wild Turkey distillery in Lawrenceburg, about 20 miles away.

Toby was not at home as the deputies were looking around the property, but when his phone rang and he answered, Sheriff Melton was on the other end and said “Toby, you need to get home”. Upon arriving, he began cooperating with the search. However, no Pappy Van Winkle bottles were found on the premises, but the sheriff had one more card to play. Pictures. The sheriff had Toby’s phone. On the phone were images of Toby in his truck with bottles of Pappy Van Winkle, but know one knew that they were not the bottles in question.  For the sheriff, the evidence was enough. He placed him under arrest and declared the mystery solved. Sheriff Melton alerted the media, of course, and told the world that he had his man.

The man behind the great Pappy Van Winkle heist — a story that captured the imaginations of bourbon lovers and casual onlookers everywhere — was none other than Toby Curtsinger. The sheriff had his mastermind. 

Or did he?

Gilbert “Toby” Curtsinger loved to make things happen for people. Whether it was getting a hard-to-find item or doing a favor, the rush he felt from delivering was as intoxicating as the bourbon he worked with at Buffalo Trace Distillery. A charismatic man with a wide circle of friends, Curtsinger had the perfect personality — and connections — to build an underground bourbon supply empire. But his penchant for pleasing others and profiting from it, would ultimately pull him into the center of Pappygate.

It all began on the softball field. Curtsinger, who had been working at Buffalo Trace since 1988, spent a lot of time hanging with his buddies on the field.  The competition and the feeling of success and winning fueled their friendships.  His team was made up of friends with various jobs: truckers, police officers, and even fellow distillery workers. Not only did they bond over the game, but they shared drinks, attended parties of their kids together, and even the occasional use of illegal steroids to stay strong and sharp. Many times while hanging out, Toby would show up with a bottle he grabbed at the distillery. You see, Toby had grown up at the distillery seeing workers sneak bottles out or take a cup of white dog from the production line. Guards looked the other way, and pocketing a little whiskey seemed like a harmless perk. So when he grabbed a bottle here or there for friends, it didn’t feel wrong — just business as usual.

As life moved on and kids came into the picture, Toby’s wild days calmed down. But one night in his kitchen, sipping on some Pappy Van Winkle with a friend, a casual suggestion sparked his next adventure. This was the time period when the reputation of Pappy Van Winkle bourbon had been exploding. His friend mentioned people would pay good money for a bottle of Pappy like he had. Toby shrugged off the idea but gave him two bottles from his personal stash. The next day, that same friend returned with a fat wad of cash — more than Toby made in a month — and a note: We’ll take anything you can get. Tempted, Toby began looking into bourbon’s secondary market online and saw bottles of Pappy fetching thousands of dollars each.

The lure was too great.

Toby’s job gave him access to premium bottles. One day in the tasting lab, he noticed four bottles of Pappy Van Winkle 20-Year. When he mentioned that collectors would pay $1,000 a bottle, the lab worker grinned. “Sure,” he said. From there, Toby’s bourbon empire began to take shape. His network of buyers grew as he rubbed elbows with judges, doctors, lawyers, and even politicians at high-stakes poker games. He would bring rare bottles to the table, and orders started pouring in.  

The demand became overwhelming so some of Toby’s old softball teammates and distillery friends joined in, taking bourbon for personal profit. One friend, desperate for cash, pulled up to Toby’s house late at night with a truck bed full of Eagle Rare cases. Toby knew this could be trouble , so he quickly made two phone calls and to his surprise, moved the entire load. In addition, his friend at Wild Turkey offered barrels from the loading dock and Toby didn’t hesitate. Soon the operation became a well-oiled machine.

Then in 2013, when news broke of the missing bourbon, Toby and his friends grew concerned.  However, as the investigation stalled, Toby began to feel a sense of relief and a growing confidence.  

“I was rubbing elbows with guys in law enforcement, court officials, local, state, and national politicians,” he later said in the 2 part episode of the Netflix documentary called Heist. “I felt like nothing was going to happen.”

Toby’s luck ran out when that call came from Sheriff Melton and told him that he needed to come home.

The search of his house turned up illegal steroids, a stockpile of guns, and stolen bourbon — but again, no Pappy Van Winkle bottles. The sheriff pressed him for names, but Toby refused to snitch. He wouldn’t betray the people he drank with, played softball with, and did business with. But his heart sank into his stomach as he remembered his phone.

When the FBI analyzed Toby’s phone, it became a treasure trove of evidence. Text messages, calls, and connections mapped a network of illegal bourbon distribution. The web of people involved became clear. Law enforcement then began to leverage Kentucky’s organized crime statute to charge Toby with responsibility for the entire operation. As investigators pressed, his softball friends cracked under pressure. Given immunity deals, they detailed the thefts and deliveries. Soon, even people who hadn’t been questioned or were even on the list of names to interview, started showing up with bourbon, claiming they had bought it thinking it was legitimate.

The media circus at the press conference was unprecedented, with national and international news outlets descending on Kentucky. Toby was branded as the Kingpin of Pappygate, the mastermind behind the great Pappy Van Winkle heist.

The trial dragged on for three years. Toby’s wife, although implicated, avoided jail as she really had no idea what was going on. Finally, in 2018, after maintaining his innocence for two years, Toby reversed his position and pled guilty. He was sentenced to 15 years in prison and the world figured that the great mystery of Pappygate was over. But there was one problem, what the world did not know was the real thief behind the missing 200+ bottles, walked right out the front door of the police station after admitting to stealing the bottles— you see during the investigation, a man named Greg Anglin, the man who Toby had originally told that Pappy Van Winkle bottles could bring over a thousand dollars on the black market, had confessed to stealing 17 cases of Pappy Van Winkle. Anglin played his get out of jail free card, as he had been granted immunity for any wrongdoing when investigators were trying to dig up more dirt on Toby. Sheriff Melton, eager to tell the world he had his kingpin, had pinned the wrong man, and let the real culprit walk away with a smile on his face.

And so, after years of investigation, tens of thousands of dollars spent, and a media circus that stretched far beyond Kentucky, Pappygate came to a dramatic close, only with the wrong man.

But for Toby, the story didn’t end with his fall from grace. He was granted shock probation just one month into a 15-year sentence (when offered it is typically for a first time offender, one who does not pose a threat to society, usually for a family man. They serve a short sentence 30-180 days, and then are placed on probation) With being given the opportunity, Toby seized the chance to rebuild. As of 2021, he was working as a painter in Frankfort, focused on supporting his family and restoring his reputation. His probation expired in 2023, marking the close of a chapter filled with misjudgments but not without redemption.

Anyone can make mistakes. Bad choices doesn't always make make bad people — but they do make lessons. Toby Curtsinger, once a man drawn into a world of temptation and shortcuts, now stands as proof that the past doesn’t define the future. His story isn’t just one of bourbon theft; it’s a story of turning things around, one honest day at a time.

As for Buffalo Trace, before the media frenzy over the theft of Pappy Van Winkle, it was just another distillery quietly making bourbon. While Pappy Van Winkle had a loyal following among bourbon aficionados, most people had never heard of the label—or the man behind the name. But sometimes, a spark of infamy can ignite unexpected fame. One could argue that while thefts are rarely a blessing, Pappygate became a twist of fate that elevated Buffalo Trace’s brand to global renown. Their name crossed oceans, and suddenly, the Pappy product was the stuff of dreams—bourbon with a story so irresistible, people craved it as much for its mystique as for its taste. Visitor traffic surged at the distillery, and demand for their entire lineup—George T. Stagg, Weller, Elmer T. Lee, Eagle Rare, EH Taylor, and even the flagship Buffalo Trace—soared to unprecedented heights.

Sometimes, fortune comes disguised as misfortune, and the thief who took your treasure may just turn you into a legend.

1. Inside the Great Pappy Van Winkle Bourbon Heist by James Higdon on Thrillist. June 29, 2021

2. The Heist: The Bourbon King. A Netflix documentary

3. Whiskey regrets: Who’s talking and who’s not in the new Netflix series on ‘Pappygate’ by Janet Patton of the Lexington Herald-Leader