Behind the Scenes with Preston Van Winkle: Family History, Hype, and Heart

Welcome back, bourbon enthusiasts and listeners of the podcast! If you have been following our journey here at Bourbon, Brass & Beyond, you know we have had the absolute privilege of speaking with some incredible names in the spirits industry. But every so often, an opportunity comes along that feels less like a standard interview and more like stepping into a living piece of American history. Recently, our team had the chance to sit down with Preston Van Winkle of the legendary Old Rip Van Winkle family. It was an experience filled with deep heritage, incredible insights, and, as it turns out, a heavy dose of unexpected podcasting drama.

In this post, we are going to expand far beyond the headlines and dive deep into what it was really like behind the scenes. We will explore the down-to-earth nature of the Van Winkle family, their refreshing approach to grounded pricing in a world gone mad with secondary markups, and why meeting Preston was about so much more than just tasting rare whiskey. Whether you are a seasoned collector chasing unicorns or a casual fan who just appreciates a good pour, there is a lot to unpack about the reality behind the myth of Pappy.

Introduction: Meeting Bourbon Royalty and Surviving Lost Audio

Let us set the scene for you. When you get the green light to sit down with bourbon royalty, expectations are naturally through the roof. We spent hours preparing our questions, setting up our mobile recording rigs, and dreaming about the stories we were going to capture. The interview itself was an incredible two-and-a-half-hour marathon of conversation covering family history, brand evolution, charitable endeavors, and the intricate science of barrel aging. Preston Van Winkle was generous with his time, deeply engaging, and an absolute joy to talk to across the board.

And then came the heartbreak that every podcaster dreads. Following the recording session, we discovered a playback failure that wiped out the vast majority of our inside audio. Imagine sitting across from one of the most sought-after names in the entire spirits world, having an unforgettable conversation, and then realizing the digital gods did not want to cooperate. Panic set in briefly. However, as we quickly realized, the human memory and the impact of a genuine encounter cannot be erased by a corrupted audio file. Along with our guest Alex Derthick, we turned this technical disaster into an opportunity to reflect on what truly mattered about the visit. The lost audio forced us to look past the microphones and focus on the core takeaways of the experience, proving that sometimes the best stories live on in our impressions rather than on a hard drive.

Meeting Preston Van Winkle: Down-to-Earth Hospitality and Family History

When you hear the last name Van Winkle, your mind immediately drifts to astronomical secondary prices, glass display cases behind bulletproof glass, and lines stretching around liquor stores at dawn. You might expect corporate coldness or an air of untouchable exclusivity. But the reality of meeting Preston Van Winkle shatters those preconceived notions instantly. Setting foot in their low-key office environment felt less like entering a corporate empire and more like being welcomed into a family home. There were real family photos on the walls, intricate family trees mapping out generations of distilling heritage, and an undeniable warmth that immediately put everyone at ease.

Preston could easily have given us twenty minutes, posed for a couple of quick photographs, and sent us on our way. Instead, he spent hours hanging out, talking candidly about the legacy of his great-grandfather Julian "Pappy" Van Winkle, sharing stories about the brand changes over the decades, and even taking the time to sign a bottle of the 23-year expression. He spoke about philanthropy, the history of the brand, and the realities of running a multi-generational family business. It was immediately clear that despite the global craze surrounding their whiskey, Preston remains fundamentally grounded. He is a guy who respects the craft, respects the people who enjoy the product, and has managed to keep his feet firmly planted on the ground despite the hurricane of hype swirling around the family name.

Tasting Notes and Preston's Secret Advice

You cannot spend time with a Van Winkle without talking about the juice itself, and Preston offered some incredible sensory insights that every bourbon drinker should take to heart. When you are dealing with ultra-aged, high-end bourbons, there is a temptation to treat them with hyper-reverence—swirling the glass aggressively to coat the sides and diving right in with your nose. According to Preston, however, we are often doing it all wrong.

During our time together, Preston shared some specific tasting advice that completely changed how we approach our pours. First off, he reminded us not to swirl the glass too aggressively. Doing so can release an overwhelming wave of ethanol right off the bat, masking the subtle, delicate notes that make these older bourbons so special. Instead, he recommended a much gentler touch and highlighted a great little trick: literally blowing gently across the top of the glass before nosing to clear away that initial heavy ethanol sting. It is a simple, practical piece of advice from someone who has nosed more legendary whiskey than most of us will ever see in a lifetime. Furthermore, Preston showcased some impressive sensory skills during our discussions, effortlessly identifying subtle cues in different pours and reminding us just how much craftsmanship and science go into every single bottle bearing their name.

Combatting the Hype: Grounded Pricing Versus the Secondary Market

One of the most refreshing aspects of our conversation with Preston was his perspective on the insane secondary market and collector culture. Let us be honest: the markup on Van Winkle products in the wild can be staggering, often reaching thousands of dollars above retail price. For the average enthusiast, finding a bottle at a fair price feels like winning the lottery.

Preston and the Van Winkle family are acutely aware of this phenomenon, and they take a very deliberate stance against it. While they cannot control what happens once a bottle leaves the distribution chain, their approach to pricing remains intentionally grounded. They want their whiskey to be opened, shared, and enjoyed with friends and family, not locked away in a safe as an investment vehicle or flipped for a quick profit. During our chat, we discussed the frustration surrounding flippers and unjustified markups. Preston’s philosophy reinforces the idea that bourbon is meant to be poured, not hoarded. The family understands that the skyrocketing hype is a double-edged sword; while it speaks to the incredible quality of the product, it also creates barriers for the authentic fans who simply want to experience the history in a glass. Keeping their baseline pricing reasonable is their way of keeping the brand connected to the real community.

Comparing the Lineup: From Lot B to the 15-Year Standout

No bourbon conversation is complete without diving deep into bottle comparisons, and our post-interview reflections gave us plenty of room to analyze the Van Winkle lineup. We compared notes on several expressions, looking at how the juice evolves across different age statements and mash bills, and even bringing in other heavy hitters from our own collections—like Eagle Rare 17, Stagg, William Larue Weller, and Elijah Craig 15—to see how they stack up.

One of the focal points of our discussion was the legendary Old Rip Van Winkle 10-Year and the Van Winkle Special Reserve 12-Year, affectionately known as Lot B. We talked about the history of Lot B, its evolution from the old store-pick concept, and how it serves as an incredible gateway into the profile. However, when the dust settled on our collective tasting and debating, one particular bottle emerged as the undisputed champion of the lineup: the Van Winkle Family Reserve 15-Year. If you ask people who have truly tasted their way through the collection, the 15-year consistently wins the title of the bottle where the "juice is truly worth the squeeze." It hits that sweet spot of intense oak extraction, rich caramel, and deep spice without tipping over into bitter territory. We also touched on the elusive Van Winkle rye, noting why it remains arguably the rarest bottling in the entire portfolio and a holy grail for collectors worldwide.

Conclusion: Why Bourbon Is About Connection, Not Resale

At the end of the day, losing our audio recording turned out to be a blessing in disguise. It forced us to strip away the technical elements and focus on the human core of what happened in that room with Preston Van Winkle. Yes, the whiskey is phenomenal. Yes, the history is rich. But what truly resonated with our team—and what we hope came across in our discussions—is that bourbon is ultimately about human connection.

Preston reminded us that a bottle of whiskey is just liquid in glass until you share it with the people you care about. The stories, the laughter, the shared sensory experiences, and the mutual respect for the craft are what make this community so special. If you want to hear all about how we survived the lost audio, our deep dives into the science of barrel char, and the rest of our reflections on this unforgettable encounter, you need to check out the full podcast episode.

Head over and listen to the complete discussion right now by checking out our official Recap: Preston Van Winkle Interview and #Bourbon Talk; Ep. 84. Trust us, you do not want to miss it. Pour yourself a great glass of whiskey, pull up a chair, and join us as we celebrate the history, the heart, and the incredible people behind the bourbon we all love.

Also check out the interview from Episode 81!

Cheers!