We are in the whiskey business, not the business of whiskey; we are in the hospitality business not the business of hospitality. Perhaps it is a minor distinction that doesn’t make perfect sense, but it does to us. It is the product, the result, the work that comes first - not the profit or accolades earned, (although he certainly and rightfully earned plenty of those).  Rather it was the commitment and promise that he made - to himself, his family, his business partners, and most importantly - to his customers, that reigned supreme. 

"We make fine bourbon at a profit if we can, at a loss if we must, but always fine bourbon." These words have defined a man, a legacy, and a business for so long, yet they haven't lost any of their luster. Nor have they been worn down or lost to history. They are as loud and necessary as they were the day they were first stamped upon the plaque that still adorns the distillery, and our minds and hearts, to this day. 

He never wavered from this commitment. He was famously quoted as saying "you can't make good bourbon when  you speed things up." He was staunchly adverse to cutting corners, and knew that the key to a good thing was to let the work, the time and the ingredients speak for themselves, "no chemists ever did anything for our business, and you can tell them I said that!" 

For a man so committed, Pappy was equally as known for his legendary, larger than life personality. His charm, his wry sense of humor and appreciation of (and ability) to deliver a punchline were naturally part of his demeanor. While he was serious about his work, he didn't take anything too seriously - least of all himself. He loved his family, his work, and he knew how to enjoy life. Visiting the offices felt more like visiting a home, or friend, and board meetings were more like impromptu lunches, walkabouts or tours. 

It's no wonder that the brass key chain that hung on his office door - meant to represent the five keys of the bourbon distilling process - came to equally represent the keys of hospitality. The old southern traditions of warmth, hospitality, and of course, the absolute enjoyment of the finer things in life. These weren't just factors in how he lived his life, they were  also woven throughout his approach to business. Perhaps, therein is the true key to his success on both fronts.

These are the keys that we continue to rely on - both as our own personal and professional guideposts - as well as an important element we weave through our own work with Pappy & Company and that we hope to deliver on with each new product we make and each partnership we embark on.

He loved to hunt, and in his later years, really enjoyed an afternoon nap. He was very expressive about his desire to enjoy these finer things, he preached moderation, and was a great example in living life with his priorities in order. Pappy loved to golf and is legendary for another surprising element of his time on the links - his beloved caddy...was his dog. His trusted companion Thunder, seen here with him serving as his caddy with a specially rigged up harness on the golf course at Louisville Country Club, is an image just as representative of who Pappy was and how he lived his life. This is easily one of the most enduring images we have that sum up this character who continues to loom so large in our collective memories. 

As evident in his life, his work and the images that continue to represent him - he enjoyed life - and he enjoyed bourbon and cigars.  Inextricably linked in their enjoyment, and (in the everlasting iconic image of Pappy) -it is no secret that these two luxuries complement each other quite well. So as we began to think in earnest about product development when we started Pappy & Company 10 years ago, and discussed the most authentic and genuine ways to share his legacy with all of you - it was absolutely natural that we do so with those very things - bourbon + cigars. 

Now we are not cigar makers. We are the very proud fourth-generation of an entirely self-made man's bourbon legacy - so we needed a partner. A partner who understood their world as deeply and as fully as we understood ours. A partner who was peerless in their industry and who was equally as committed to quality as Pappy Van Winkle was himself. A partner we have now worked with since 2014, and just as with Pappy, whose associates became family - our partnership has blossomed into a life-long friendship as well.

Pappy & Company X Drew Estate

Finding the right partner wasn’t easy, but deciding to work with our partner certainly was. Undoubtedly the best in their field, as only a cigar bearing Pappy’s name could be, Drew Estate was a natural partner for this endeavor. We brought our ideas, our heritage and our desire to create a signature line of cigars in Pappy's honor, and they brought their unmitigated expertise, commitment, dedication, innovation and excitement. 

Drew Estate was founded by partners Jonathan Drew and Marvin Samuel, two college friends who, in a similar fashion to Pappy's story,  didn't start with an inherited family business - but rather a dream. From their early days in Brooklyn, New York, to their sprawling factory based in Estelí, Nicaragua, theirs was not a story of overnight success, but rather hard-fought. A similar combination of passion, commitment and dedication led them to where they are today, and where we are proud to consider them one of our very first partners.

Our first foray into cigar production with Drew Estate was to create a cigar that was as intrinsically linked to the legacy of Pappy Van Winkle as possible. We produced a batch of barrel-fermented cigars, using Kentucky fire-cured tobacco that has been pressed in retired Pappy Van Winkle bourbon barrels for a cigar boasting a completely unique and entirely Pappy flavor. We were fortunate to visit Nicaragua in 2017 to see first-hand just how incredible the operation was. Learn more about that trip here. 

Every Pappy Van Winkle Barrel-Fermented Cigar is rolled by hand, the old fashioned way, in La Gran Fabrica Drew Estate factory in Estelí, Nicaragua, just as Pappy himself would have insisted. We offer a few year round vitolas, our Churchill, Toro and Robusto offerings, with limited-release vitolas throughout the year. Often requiring specialized training, such as the beloved Flying Pig, these cigars boast a unique flavor - reminiscent of our family's bourbon, with signature Pappy Van Winkle flavor notes of chocolate, coffee, cedar with undertones of charred wood and an overall smoky sweetness. These specialty  small batch cigars feature a maduro Tapa-Negra style Kentucky fire-cured and Pappy Van Winkle Barrel-Aged wrapper over a base of Mexican San Andres with a filler of Nicaraguan and Kentucky Fire-Cured, Pappy Van Winkle Barrel-Aged tobacco.

We expanded our cigar line with our Tradition Blend in 2019, to both complement and honor Pappy Van Winkle bourbon and his legacy. Hand selected by our dad, Julian Van Winkle, the Tradition blend was chosen to best represent and accompany Pappy Van Winkle bourbon. Small batch cigars made in Estelí, Nicaragua, the Tradition Blend is woody and spicy, with notes of ground black pepper over a base of cinnamon and cedar. Featuring an Indonesian Sumatra binder, with Dominican Republic and Nicaragua filler, and an Ecuadorian Habano Oscuro wrapper, these pair well with American Whiskey's and bourbon. We offer the Tradition Blend in a selection of year round vitolas - Churchill, Toro and Robusto, as well as limited-release offerings throughout the year.