
The bourbon boom we’ve experienced in the United States this past decade or so just about rivals the cigar boom that occurred in the 1990s. There are hundreds of options for consumers to select from, but Pappy Van Winkle is the holy grail for many enthusiasts. It’s coveted because Pappy Van Winkle is sold in limited annual quantities. It’s not a brand that’s reached mythical standards for no good reason. The liquid matches the myth.
Does a hypothetical $600 pour tickle your fancy? A record-breaking sale of Pappy Van Winkle Family Reserve 15 Year took place at the 2021 Art of Bourbon Auction. It sold for $15,000. Not too shabby. There are a variety of expressions of Pappy if you can get your hands on them. They run the gamut. For example, Van Winkle Special Reserve 12 Year ($899.99-$1,599.99) to Pappy Van Winkle’s 23 Year Family Reserve ($5,000-$8,950).
Making quality bourbon has been a family business for four generations. We had the opportunity to catch up with Pappy’s Carrie Greener. Along with her sisters, Louise and Chenault, they are the keepers of the flame. Their Pappy & Company store, based appropriately in Louisville, Ky., features product lines that commemorate and modernize all things Pappy. During our conversation, we were able to touch on the value of looking back at an iconic bourbon, and a take look at the future.
Pappy was a salesman, a man of his word, a true character who was able to be himself and always do the right thing.
C&S Magazine: Tell us about your current role with Pappy Van Winkle Bourbon and Pappy & Company.
Carrie Greener: I started this business in 2013 with my two sisters, Louise and Chenault (we are actually triplets). I like to say that I’m in charge of the “front facing” part of the brand. My primary role is on product development, but I also work closely with marketing, events, partnerships and general branding. Our bourbon brand is famous, but it’s actually a small family-run business. We realized that there wasn’t any merchandise associated with our family’s brand, and that’s how we got into the business. We started creating merchandise branded with bourbon and the Pappy name, and then it just evolved from there.
How rewarding is it for you that Pappy Van Winkle is an iconic brand?
Honestly, I don’t often stop to think about it, but when there’s a special occasion or acknowledgement, it makes me realize how grateful I am to have this incredible family legacy. It’s not always easy, but I feel so thankful for the opportunity. The idea that we can impact so many potential customers beyond the bourbon consumers is really rewarding. It makes me feel like we are giving back to a greater community, and we’re extending our family’s values.


There was no master plan to make this an aspirational or elite brand, so I think we’re a great example of what can happen with hard work, dedication and staying true to yourself and your values.
How does the Pappy Van Winkle legacy inform your goals with the brand today?
The values of our great grandfather Pappy are at the forefront of everything we do today. Pappy was a salesman, a man of his word, a true character who was able to be himself and always do the right thing. My grandfather, and dad carried on these same values, not by being told, but by seeing and doing. It’s all they knew. Through building Pappy & Company and being fourth generation Van Winkles, we’ve realized that these values have also come naturally to us. It’s important to formalize them, and pave the way for future generations. We keep it fun. We are family-focused. We do the right thing. We put quality first. We hustle.
What are the aspects that make Pappy Van Winkle so sought-after, elite, aspirational and collectible?
Well, I think it’s a multitude of things. We have a real story. A real brand with a real person on the label, and a real family behind it. Consumers seek that in a brand, but it’s hard to find these days. Also, the simple psychology of “you want what you can’t have.” Because the bourbon supply can’t keep up with the demand, there’s been hyperawareness and focus on a brand that makes an exceptional product. There was no master plan to make this an aspirational or elite brand, so I think we’re a great example of what can happen with hard work, dedication and staying true to yourself and your values. And while we appreciate the following that has made us a collectible and sought-after brand, we always try to stay humble to who we are.
Tell us about your passion for bringing fine cigars and bourbon to the world.
Pappy loved cigars, so it was a natural product extension for us. When it came to making the actual blends and determining what kind of cigars we wanted to sell, we knew it had to uphold the same quality and distinct flavor profile that our family’s bourbon possesses.
It’s our family’s name on the product, we are closely connected to our brands, so it’s in our blood and all we know is what it takes to make such quality products. We feel very thankful that Drew Estate Cigars shares the same standards for excellence, so together we can offer a cigar collection like nothing else you’ll find in the premium cigar market.


Can you recommend a pairing for our readership?
Absolutely. We believe firmly that cigars and bourbon are meant to be enjoyed hand in hand. But we also don’t think or expect that it has to be PVW paired with our cigars. Given that we have two distinct blends: our Barrel Fermented and our Tradition, as well as an array of cigar sizes and unique limited-edition cigars, there really is a cigar style and pairing for everyone. For example, our Barrel Fermented blend pairs really well with rye. Its rich flavor profile is nicely complemented by the spicier flavor notes that rye possesses. However, our Tradition blend is a more classic cigar and pairs well with bourbon and American whiskeys.
What should we be on the lookout for in 2022 and beyond?
It’s already been an exciting year for us. We recently released two new cigars, our Barrel Fermented Gordo and our Barrel Fermented Corona Viva, as well as a number of limited release cigars that are only available for a very limited time in limited numbers. Our cigar accessories line was enhanced by the release of our custom humidors earlier this year as well.
We’re excited to be launching a very special bar accessories collection early next year, pieces inspired by family heirlooms, yet made for everyday use and perfect cocktail and entertaining accouterments.
We’re also working hard to expand our culinary offerings. The quality of our barrels and the multitude of uses we’re finding for them after the barrels have been dumped are endless. They add a special flavor profile to the gourmet food products we create. These take time to develop, and we’ll never rush the process. We want to make sure that quality comes first, and that our family’s legacy and values stand behind anything we release.
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Randy Mastronicola is the Executive Editor of Cigar & Spirits Magazine.