The Pappy Van Winkle Heist That Wasn’t

This story was originally written for Bloomberg BusinessWeek over the summer. Instead of running it they turned it into a highly-truncated cartoon thing that, being honest, was pretty darn clever and probably more appropriate for the subject matter than a 3,000-word story.Still, I’d like to have the words I wrote for it all preserved someplace, so here they are.

​On March 11, 2015, an anonymous tip was texted to the Franklin County Kentucky Sheriff’s Department that Gilbert “Toby” Curtsinger, a longtime employee of the Buffalo Trace distillery had some stolen barrels of bourbon on his property. A search warrant was executed and deputies drove out to Curtsinger’s house on a winding country road west of Frankfort. Stolen bourbon is not unusual in bourbon country, but Franklin County Sheriff Pat Melton believed that this tip was about something more than your typical bootlegger. He believed that it might be leading him to the Pappy Van Winkle Bandit.

If you’re even a casual consumer of bourbon, chances are you’ve heard of Pappy Van Winkle. It’s the rarest of the many varieties of bourbon made by the Buffalo Trace Distillery and, indeed, the rarest bourbon variety of them all. Pappy, as it is known colloquially, is extraordinarily hard to find. Just 8,000 barrels are produced each year, compared to the millions of barrels of mass market brands like Jim Beam or its Tennessee cousin, Jack Daniel’s. Bar patrons pay upwards of $100 for a single pour. Aficionados who are lucky enough to win lotteries for the privilege of buying it at retail snap up bottles for as much as $300. Those not so fortunate, but who still want the stuff, routinely pay thousands for a bottle on the black market.

​On October 15, 2013 Buffalo Trace reported that a little over 200 bottles of Pappy, with a market value of around $26,000, had gone missing. Sheriff Melton characterized it as a “heist,” and characterized the stolen product as “The Mac Daddy” of bourbon. The theft made international headlines, with bourbon enthusiasts inside and outside of the industry speculating about who did it, marveling at the audaciousness of it all and, perhaps, wondering if the theft made it more or less likely that they themselves could get their hands on a bottle. When that tip came in, pointing a finger at a man who had inside access to the place where Pappy was born, Sheriff Melton believed he was about to crack the bourbon crime of the century.

When deputies arrived at Curtsinger’s property they found five barrels of bourbon under a tarp, the name of the distillery painted over in an effort to hide its provenance. Curtsinger, alerted to the raid by his next-door neighbor, came home and waited patiently on the front porch for the deputies to finish their business. As far as police raids go, it was a pretty calm affair.

The barrels of whiskey were later discovered to be from a completely different distillery than Buffalo Trace. Deputies did find photos of five or six bottles of Pappy Van Winkle bottles on Curtsinger’s cell phone, taken in what appeared to be the front seat of Curtsinger’s truck. He was arrested. That evening Sheriff Melton met the media and, despite the fact that not a drop of Pappy Van Winkle bourbon was found on the premises, declared that he had solved the Pappy Van Winkle heist and that Toby Curtsinger was the kingpin of the whole operation.

Curtsinger and, eventually, eight accomplices, including his wife and father-in-law were charged with bootlegging and drug dealing (there were loads of illegal steroids found on the premises, unrelated to the bootlegging) and Curtsinger himself was charged with operating an organized crime ring under Kentucky’s racketeering laws, all of which carried potential prison terms of 30 years or more. Everyone posted bail and, over the next three years, the case crawled along, with all but one of Curtsinger’s co-defendants taking plea deals and his father-in-law having charges dropped against him in their entirety for lack of evidence. Last September Curtsinger pleaded guilty to theft, receiving stolen property and trafficking in controlled substances, all either misdemeanors or felonies of reduced severity from the original charges. On June 1, he was sentenced to 15 years in prison.

For most, Curtsinger’s plea and sentencing closed the book on The Pappy Van Winkle Heist. It’s probably worth noting at this point, however, that there is little if anything to suggest that there was a Pappy Van Winkle Heist to begin with.

“I ain’t totally innocent on a lot of this stuff, but I ain’t the only one what’s guilty,” Curtsinger told me when we met in Frankfort at an empty Cross-Fit gym owned by his wife late one Sunday afternoon last January. It was the first time he’s spoken publicly since his arrest over three years ago. He agreed to meet with me because, he said, he was fed up at being portrayed as some sort of master criminal who pulled off some sort of audacious heist. Curtsinger did not back away from that to which he had recently pleaded guilty — he admits he did some crimes and knew he was about to do some time — but he bristled at the label of “The Bourbon Bandit” that had been bestowed upon him by Sheriff Melton and the press. According to Curstinger, there are a lot of bourbon bandits and there always has been. And in no event was there ever a single theft of any great quantity of Pappy Van Winkle.

Toby Curtsinger was taught about bootlegging on his first day on the job back in 1989, when the Buffalo Trace Distillery was known as the Ancient Age Distillery and bourbon was by no means a trendy drink. After his first shift, the then-20-year-old Curtsinger was taken by coworkers to a room where barrels were filled from the still. Plastic cups were distributed and he and a half dozen of his coworkers partook in the un-aged “white dog” which would become bourbon after some time in a barrel. This was not a party for a new coworker, mind you, it was an everyday occurrence. Curtsinger says that, from that day on, “I’d see people drinkin’ on the job, I’d see them pass out and you’d roll ‘em to the side and go on about your business. Everybody watched out for everybody. Nobody got hurt.”

This would not be news to anyone familiar with the industry. Indeed, for as long as there have been distilleries, there have been whiskey thefts. For the most part this involves what Toby observed in his early years at Ancient Age and Buffalo Trace: employees drinking on the job or emptying bottles into mason jars and carrying them home in their lunch buckets. Whiskey Advocate writer Charles Cowdery has referred to this sort of theft as “the perfect crime,” with most of the evidence disappearing the moment the thief drank it. It’s a crime, Cowdery says, that “has been committed thousands of times in every era and at every distillery.”

What wasn’t common, however, was high-volume theft for purposes of resale. The reason is simple: until pretty recently, bourbon wasn’t all that valuable.

Yes, bourbon was popular in the Rat Pack era, but between the mid-60s and the mid-70s, bourbon’s share of the liquor market dropped precipitously. Dark bars with strong drinks made way for fern bars which served fruity concoctions made with vodka, rum and tequila. Bourbon became a drink for grandfathers and rednecks. In the face of plummeting demand, many distilleries closed their doors or resorted to gimmicky, selling bourbon in novelty ceramic crocks depicting hillbillies and country kitsch in order to move product. It was Maker’s Mark’s surprisingly effective positioning of itself as a luxury brand beginning in the 1980s that made people see bourbon in a different, more expensive light.

As the bourbon market began, slowly but surely, to make room for higher-end products, Julian Van Winkle III, a third-generation distiller whose family distillery had been sold off and who had been sitting on a warehouse full of aging, un-sold product and some of those kitschy hillbilly crocks, got the brilliant idea of bottling it, slapping a photo and the name of his grandfather, Julian Proctor “Pappy” Van Winkle, on it and marketing it as “ultra aged” bourbon, a product sector which, to that point, did not exist. Thanks to early rave reviews in liquor-industry trade publications and the glossy retro sheen applied to bourbon by popular fare like Mad Men, by the late-2000s, Pappy Van Winkle had serious cachet among bourbon insiders. Hipsters and scenesters, not necessarily aware of what makes a good bourbon good but adept at elevating anything they perceive as exotic or expensive, jumped on the Pappy bandwagon, and the price began to climb.

The bourbon industry and its promoters have long traded on legend. Nearly every distillery in Kentucky has, at some time or another, made a claim to being the oldest or longest in continual operation, with connections to the original families and frontiersman who founded them. In the case of Pappy Van Winkle, the lie is that the older and more expensive a bourbon is, the better it tastes.

“It’s a status symbol more than anything else,” says a former bartender at a bourbon-centric bar in Atlanta, who requested anonymity so as not to be seen speaking ill of his clientele. “It’s the product of an echo chamber in which people hear a thing and repeat the thing without ever asking whether it’s true.” He says that, beginning in 2012 or 2013 guests, whose level of wealth was typically inversely proportional to their knowledge of bourbon, would ask for Pappy by name even before looking at the spirits list, simply because they heard it was the best. Over time the bar’s owner increased the price of Pappy to the point where, he hoped, it would not sell. His thinking: he’d prefer to always have it on the back bar, so people could see it and think of the bar as a place were discriminating people chose to drink because it was good enough to have Pappy.

Many in the distilling business echo this assessment.

“Everyone has this idea that the older something is or the more expensive something is, the better it is,” says Jackie Zykan, the Master Taster for Old Forester Distillery in Louisville. “It’s understandable and whether it’s whiskey or anything else, they tend to believe that. But the most important thing for a good bourbon is balance.”

Zykan appreciates the visibility that super rare and premium labels like Pappy Van Winkle have brought to the bourbon industry, but she laments how it has skewed people’s idea of what makes a good bourbon. Zykan thinks of the variables which go into bourbon — the mash bill, the yeast, the barrels and how they are stored, among other things — as “levers,” and that a distiller’s job is to pull those levers in just the right way to make a good, balanced bourbon.  Aging is a lever too, but it’s only one lever.

“There is absolutely, 100%, such a thing as over-aging whiskey,” Zykan says. Oak, which gives bourbon its flavor, can be rough stuff. “If bourbon is in the barrel too long you can get such concentrated oak notes that you’re not getting the balance. You’re not really tasting the grain notes, if they’re there at all. You’re just getting an oak bomb.” Zykan likens it to drinking an oak coffee table. Other distillers have referred to it as “chewing on a pencil.”

“It’s old bourbon, but that don’t make it good,” Curtsinger says. “Julian Van Winkle comes in and puts his name on one barrel and doesn’t put his name on another. One becomes Pappy. One becomes somethin’ else. They ain’t all that different.”

Pappy was different in one important respect, however. It was hard to find and people were willing to pay an awful lot of money for it. For Toby Curtsinger, the rest was just a matter of simple economics.

According to Curtsinger, his criminal history begins in 2003. He was working in a building at Buffalo Trace where bourbon which wasn’t up to production standards was kept in blue plastic barrels marked for disposal. At one point that year more than the usual number of barrels had accumulated and his supervisor was getting nervous. “Stashing” putatively defective bourbon for later sale is a serious violation of protocol which, in the past, was used by unscrupulous distillers to avoid federal tax liability. Curtsinger says the supervisor told him to get rid of the blue barrels as soon as possible, which meant to take it to an on-site treatment facility before it could be safely dumped down the drain.

“I made a joke with him,” Curtsinger says. “If he’d just write me a barrel pass to get past security, you’ll never see it again.” Surprisingly, the supervisor did just that and Curtsinger left with a few barrels free bourbon in his pickup truck, with the same paperwork that people buying barrels of bourbon used to leave the property. “I made a little money off of that,” he admitted, selling it in mason jars to friends and acquaintances happy for a bargain.

Curtsinger slowly increased the size of these and similar hauls over the years. Most of the bourbon he stole was mid-level product, such as the Buffalo Trace distillery’s namesake bourbon, and lower-level product like Ancient Age. He was not alone in this, as many coworkers, he says, would take bottles or cases here or there, in amounts that could easily be carried under an arm and stashed in the back seat of a car, though Toby admits that at times he was a bit bolder, taking whiskey by the barrel. It wasn’t terribly difficult, as security was lax and the sort of bourbon he was taking was not particularly valuable. He didn’t pay much attention to the higher-end products Buffalo Trace had begun producing, such as Blanton’s and Pappy Van Winkle, precisely because, he assumed, it’d be more readily missed.

Others weren’t so cautious. One of Curtsinger’s former coworkers told deputies investigating the Pappy case that a supervisor would pay him $100 to build pallets of inexpensive liquors and hide cases of Pappy Van Winkle at the center that would avoid being counted in inventory and thus not missed when later taken off the premises. Others would simply take two or three bottles of Pappy home at a time, either for personal consumption or to sell on the growing black market. Curtsinger said he warned his coworkers about being too conspicuous but he’d also, on occasion, help them unload their ill-gotten gains. Curtsinger was known as somebody who knew everybody — he had a great number of friends he met while pursuing his hobbies in body building and semi-pro softball — and he always seemed to know someone who would buy a stolen bottle or a mason jar full of bourbon. Sometimes even a barrel.

Curtsinger was at work when news of the the 200 missing bottles of Pappy Van Winkle his the news in October 2013. He and his coworkers at Buffalo Trace were genuinely surprised that anyone would bother to report it. Two-hundred bottles of missing whiskey simply wasn’t that much. In the past, if an inventory came up that short, it would likely be written off as breakage. In hindsight Curtsinger thinks the man who reported the whiskey missing, a newer employee who was unfamiliar with how things usually worked, simply got nervous that he might be blamed for its loss and figure it was safer to call the police than to remain silent.

Curtsinger didn’t take the 200 missing bottles of Pappy Van Winkle. Indeed, there is nothing to suggest that any one person did. He was no idiot, however, and he made a point after the story broke to sell some Pappy, or whatever else he could get his hands on, leveraging the buzz about “the Pappy Heist” to get top dollar. Indeed, despite the publicity and the police involvement there were more customers now than ever. Maybe because of it, with customers drawn to the idea that, maybe, they were buying the product of a world famous crime or otherwise riding the wave of a bourbon boom that made Kentucky whiskey a luxury good or even a collectors item. Just as offering a business associate an illicit Cuban cigar was a means of cementing a bond, so too is offering one a bottle of Pappy Van Winkle.

Curtsinger sold one visiting executive nine bottles of Pappy stolen by a coworker — marked “for export sale,” which made it clear it was not legally acquired in the United States — for around $3,000. He sold a full barrel of another top-shelf Buffalo Trace bourbon — Eagle Rare — to a suburban housewife who found him through a mutual acquaintance and who wanted to get her husband a “special” Christmas gift. Many of Toby’s customers would later tell police that they believed the deals were on the up-and-up, despite the fact that they happened in parking lots and were paid for with cash. They  said they thought they were buying “extra whiskey,” whatever that means, or “bourbon written off for tax purposes.” Curtsinger says most of his customers knew that they were buying stolen whiskey—in fact, he thinks most of them assumed they were product from the famous heist.

Curtsinger did, in fact, steal a good deal of bourbon, but he didn’t have to steal as much as one might assume in order to continue making money off of it. Coworkers at Buffalo Trace and friends at other distilleries knew that Toby was good at finding buyers and would bring him most of the bourbon he sold. On one occasion a coworker showed up drunk with a few bottles of Pappy in his truck in the middle of the night, asking for Toby’s help in unloading it. Another time Curtsinger says a coworker with a drug problem simply took two cases, put it in his car and brought it to Toby in order to get some fast cash. The barrels of whiskey found on Toby’ property at the time of his arrest turned out to be Wild Turkey, dumped there with almost no warning by a friend of his who worked at that distillery, with Toby scrambling to get someone to buy it before anyone saw it.

Sheriff Melton and the prosecutors in the Pappy case have painted Curtsinger’s operation as an organized crime syndicate, but if anything, the entire operation was disorganized in the extreme. To the extent he coordinated thefts and sales with anyone, it was over text, with no attempt made to conceal the fact that they were discussing boosted hooch. “It wasn’t Goodfellas,” says Toby’s wife. “It was good ole boys.”

However disorganized the operation was — and even if there was no single theft of Pappy Van Winkle to match the legend of The Pappy Van Winkle Heist — Toby Curtsinger is paying the price for it all the same. He, quite understandably, lost his job at Buffalo Trace and spent his three years out on bail in legal limbo, working as a house painter and helping out around his wife’s gym. The social cost has been high as well. While no one had any problem consorting with a bourbon thief, being friendly with the “Pappy Van Winkle Bandit” is another matter. There are a lot of people around Frankfort who have bought and sold stolen bourbon over the years and it was never a big deal. There’s a feeling around town now, however, that the Pappy Heist ruined it for everyone and that Curtsinger, even if he didn’t do it himself, is responsible for ruining a good thing. Old friends have abandoned him and, he says, even his kids have been ostracized at school. He has has received threats since his guilty plea in the form of anonymous notes left on his windshield, telling him that if he knows what’s good for him he won’t talk about others who bought and sold stolen bourbon.

As for the legal cost, Curtsinger spent only a month of that 15-year sentence in prison before being released on “shock probation” back in July. That the prosecutors agreed to such a thing suggested that, absent ready access to massive amounts of bourbon, Curtsinger is not exactly a danger to society, even if he ain’t totally innocent.

In the meantime, all of Curtsinger’s co-defendants pleaded guilty to various charges over the past three years. None of them have served prison time for their involvement in all of this, likely because there was no single crime anyone could point to which justified it. Sheriff Pat Melton, who alone characterized the whiskey thefts as part of one big heist, thus ensuring it made headlines, lost the primary in his reelection bid in late May and will be seeking a new job come November. Apparently busting the Pappy Van Winkle Bandit did not impress all that many people in Franklin County, Kentucky.

Many in the bourbon industry suspect that Buffalo Trace isn’t altogether displeased with the publicity the Pappy Heist brought to its most treasured brand. They may have lost a few hundred bottles, some odd barrels and $26,000 in inventory a few years back, but it doesn’t seem to have harmed them that much. Last summer Buffalo Trace announced a $200 million expansion to the distillery, which includes new bottling facilities, new aging warehouses and, for the first time in the distillery’s history, cookers and fermenters which will operate 24 hours a day, seven days a week. All to keep up with a demand which created the bourbon bubble which created the black market in the first place. Buffalo Trace declined to comment on this and all other aspects of this story.

For bourbon drinkers, Pappy Van Winkle is still freely available if you’re lucky enough to win the annual lottery from a liquor store which manages to get a few bottles of its annual release. It’s expensively available if you need to find it on the still-thriving black market, where a single bottle of Pappy 23-year is currently commanding prices in the high four-figures.

All of which one may inspire one to ask whether Toby Curtsinger belongs in a jail cell or whether he belongs in the marketing department at Buffalo Trace.

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at He lives in New Albany, Ohio with his wife, two kids, and many cats.