Sipping History with Preston Van Winkle: A Conversation on Legacy, Bourbon, and Cigars

Welcome back to the podcast blog, folks! If you are anything like us, your ears instantly perk up at the mention of one specific family name in the American whiskey landscape: Van Winkle. For decades, the mere whisper of "Pappy" has been enough to send bourbon enthusiasts into a frenzy of secondary market searches, frantic phone calls to local liquor store owners, and deep online forum debates. But behind the mystique, the hype, and the coveted gold wax, there is a real, hard-working family whose dedication to craft has fundamentally changed the way the world views Kentucky bourbon.

In this upcoming episode of the podcast, we had the absolute honor and privilege of sitting down with Preston Van Winkle. As the fourth generation of the Van Winkle family involved in the bourbon business, Preston carries a legacy that is as rich, complex, and heavy as the 23-year-old juice resting inside those famous decanter bottles. We talked history, we talked the modern whiskey landscape, and yes, we even talked about cigars. In this post, we are going to pull back the curtain and give you a sneak peek at what we discussed, breaking down the history, the current lineup, and an unforgettable tasting experience that brought together the holy grail of aged bourbon and a world-class cigar.

Introduction: Meeting Royalty in the Bourbon World

When you prepare to interview someone like Preston Van Winkle, it is easy to get caught up in the celebrity of it all. After all, the brand his family built represents the absolute pinnacle of luxury spirits. Yet, the moment you meet Preston all that perceived intimidation melts away. He is warm, deeply knowledgeable, fiercely protective of his family's heritage, and refreshingly down-to-earth.  He was even so gracious after we had a technical snafu and much of the audio did not come through on the first sit down.  He met me a second time to re-record.  I am grateful for the time he spent with us, and the time he made for us the second go around.

Talking to Preston feels less like interviewing a corporate executive and more like sitting on a porch with an old friend who just happens to know everything there is to know about whiskey. We kicked off our conversation by discussing the sheer weight of the family name. How do you carry on a tradition that has become a cultural phenomenon? How do you balance the insane demand with a commitment to quality that cannot be rushed? Preston gave us some incredible behind-the-scenes insights into what it is like growing up Van Winkle, watching the brand evolve from a hidden gem known mostly to industry insiders into a global icon of luxury and patience.

The Van Winkle Legacy: Roots, Tradition, and the Pursuit of Pappy

You cannot truly understand modern bourbon without understanding the Van Winkle story, and Preston was kind enough to walk us through the foundational chapters of that history. It all starts with Julian "Pappy" Van Winkle Sr., who began his journey in the whiskey business as a salesman for the W.L. Weller and Sons company in the late 19th century. Pappy was a pioneer of wheat-recipe bourbon, a style that swaps out the traditional spicy rye grain for softer, sweeter wheat, resulting in a smoother, more approachable spirit.

As Preston explained during our chat, the family's journey has been anything but a straight line through smooth waters. Through Prohibition, corporate buyouts, and the lean years of the 1970s and 1980s when clear spirits dominated the American palate, the family fought to keep their name and their recipes alive. Julian Van Winkle Jr., and later Julian Van Winkle III (Preston's father), kept the flame burning, eventually reviving the Old Rip Van Winkle label and introducing the world to the older age-stated bourbons that would eventually make history.

We discussed the pivotal partnership with the Buffalo Trace Distillery, which began in 2002. This collaboration allowed the Van Winkle family to utilize Buffalo Trace’s incredible distilling and warehousing capabilities while maintaining strict control over the recipes, aging process, and blending. Preston shared fascinating details about how this relationship works today and how they manage to maintain the distinct Van Winkle flavor profile while scaling to meet—or at least attempt to meet—insane global demand.

Breaking Down the Bottle: A Look at Current Offerings

During our conversation, we couldn't pass up the opportunity to talk shop about the legendary Old Rip Van Winkle lineup. Each bottle in the collection has its own distinct personality, age profile, and flavor journey. Preston gave us the insider perspective on what makes each expression unique:

• Old Rip Van Winkle Handmade Bourbon 10 Year Old: Bottled at a punchy 107 proof, this is a vibrant, spice-forward expression that showcases the youthful energy of the wheated mash bill balanced with rich oak.
• Van Winkle Special Reserve 12 Year Old ("Lot B"): Often considered the ultimate crowd-pleaser of the line, sitting at 90.4 proof. It is smooth, sweet, and approachable, with lush notes of caramel and nutty undertones.
• Pappy Van Winkle’s Family Reserve 15 Year Old: Bottled at 107 proof, this expression is frequently cited by connoisseurs as the sweet spot of the entire lineup. It strikes a masterclass balance between deep oak influence and sweet, sugary brightness.
• Pappy Van Winkle’s Family Reserve 20 Year Old: At 90.4 proof, this is the bottle that put modern ultra-aged bourbon on the map. Rich, dark, leather-bound, and deeply complex.
• Pappy Van Winkle’s Family Reserve 23 Year Old: The heavyweight champion. Bottled at 95.6 proof, this is an exercise in extreme aging, where the barrel has given nearly all it has to offer, resulting in a profound, meditative sipping experience.
• Van Winkle Family Reserve Rye 13 Year Old: A reminder that the family knows their way around a rye grain just as well as wheat, offering a spicy, complex departure from their flagship wheated bourbons.

Hearing Preston talk about the rigorous selection process for these barrels was eye-opening. Every single batch is tasted and evaluated. If a barrel doesn't meet the exacting standards of the family, it doesn't make the cut. That uncompromising dedication is the real secret behind the legend.

The Ultimate Pairing: Pappy Van Winkle 23-Year and Pappy & Co. Cigars

Now, let us move to the segment of the episode that truly elevated our tasting experience to legendary status. In addition to their bourbon empire, the Van Winkle family—specifically triplet sisters Louise, Carrie, and Chenault—run Pappy & Co., a lifestyle brand offering everything from artisanal cocktail mixers and barrel-aged syrups to high-end leather goods and premium cigars.

We decided to treat ourselves and our audience to the absolute pinnacle of indulgence: pairing the Pappy Van Winkle Family Reserve 23-Year Bourbon with the Pappy & Co. Traditional Cigar.

The Cigar Breakdown

Crafted in collaboration with the renowned Drew Estate, the Pappy & Co. Traditional Cigar is engineered specifically to complement the flavor profiles of aged bourbon. You will hear Preston talk about the origins of the Traditional Pappy Cigar, and how he and his father tested them while visiting Nicaragua.  This is a great story, and will let you hear it in his words.

The Sensory Experience

Sitting down with Preston while exploring this pairing was nothing short of a religious experience for whiskey and cigar lovers. When you take a sip of the 23-Year Bourbon, you are immediately greeted by waves of dark chocolate, aged oak, leather, and a hint of dark cherry. The mouthfeel is surprisingly viscous for its age, coating the palate in a luxurious layer of flavor.

Then, you take a draw from the Pappy & Co. Traditional cigar. The smoke is rich, creamy, and aromatic. The magic happens on the finish. The earthy, nutty, and slightly sweet tobacco smoke dances with the residual oak and caramel from the bourbon, creating an entirely new third flavor profile on the palate. The cigar cuts through the heavy tannins of the 23-year-old oak, cleansing the palate and preparing it for the next sip of whiskey. It is a masterclass in pairing, proving that the Van Winkle family's expertise extends far beyond the liquid in the glass.

Bourbon For Good: The Philanthropic Arm of the Van Winkle Family

While the mystique of Pappy Van Winkle is often tied to luxury, secondary market prices, and exclusivity, one of the most important topics we covered with Preston was the family's deep commitment to giving back. With great influence comes great responsibility, and the Van Winkle family has consistently used their platform to support causes that matter deeply to them.

We discussed their ongoing philanthropic efforts, including partnerships with various charitable organizations, disaster relief efforts in Kentucky, and community support initiatives. Preston spoke passionately about how important it is for their business to be a force for good in their local community and beyond. It is easy to view a brand of this magnitude through a purely commercial lens, but our conversation served as a powerful reminder that the people behind the bottles are deeply invested in making the world a better place. Hearing Preston talk about these initiatives added a layer of profound respect to our appreciation of the brand.  Unfortunately, part of the audio which did not make it from the recording, was when Louise Van Winkle Breen joined the podcast and spoke about their Bourbon For Good Program.  We hope to revisit that soon.  

Final Thoughts and What to Expect on the Episode

As we wrapped up our conversation with Preston Van Winkle, we felt an immense sense of gratitude. Talking to someone who is actively shaping the history of an industry you love is a rare and special privilege. Whether you are lucky enough to have a bottle of Pappy sitting on your shelf, or you simply enjoy hearing the stories of the families who built American whiskey into what it is today, this upcoming podcast episode is one you simply cannot afford to miss.

In the full episode, you will get to hear Preston’s own voice telling these stories, sharing his thoughts on the future of the bourbon industry, and offering advice for those navigating the exciting—and sometimes chaotic—world of whiskey collecting. We will also dive deeper into the tasting notes, share more details about the Pappy & Co. lifestyle brand, and explore what keeps this legendary family motivated to keep pushing forward generation after generation.

Make sure you are subscribed to the podcast on your favorite listening platform and signed up for our newsletter so you do not miss the drop. Pour yourself a nice glass of whiskey—wheated or otherwise—settle into your favorite chair, and get ready for a conversation that is decades in the making. Cheers, everyone!