Ask a whiskey lover about their favorite bourbon, and you’re likely to hear the name Pappy Van Winkle. In his second book, Pappyland: A Story of Family, Fine Bourbon, and the Things That Last (Penguin Press, Nov. 10), ESPN senior writer Wright Thompson uncorks the fascinating story of one of the best bourbons in the world. The history of the brand dates back to the 1890s, when Julian “Pappy” Van Winkle Sr. worked for—and later purchased—a liquor distributor that, just before Prohibition, introduced a label called Old Rip Van Winkle. After Pappy died in 1981, his grandson, Julian III, took over operations and, through a variety of partnerships, has been running the company ever since. But this is more than just the life story of Julian III, keeper of the Pappy name and tradition. As our reviewer notes, Thompson offers “a blend of biography and meditation on any number of themes, including Southernness,” family, identity, and craft, in a genre-blending book that will appeal not just to bourbon aficionados, but to those interrogating the mysteries of authenticity and legacy. I spoke to Thompson via Zoom; the interview has been edited for length and clarity.

Early on, you note how the book expanded beyond a conventional biography of Julian and his brand. Can you discuss the process of shaping the story?

My agent suggested I should hang out with Julian and write an ode to bourbon or something, and I thought it was going to be pretty straightforward. The more time I spent with him, the more I realized we were engaged in a serious, authentic discussion about things I was dealing with in my life, like fatherhood and legacy. So I had this road map, but I thought, why don’t I write about what it’s been like to do this? In a meta way, to step out of the architecture of a book and write a book about writing a book?

This line resonated with me: “We must be intentional with our myths and stories, and we must live the lives we want our children to live.” Talk more about how that concept influenced your narrative direction.

No disrespect to Julian, but I wanted this to be more of a story about family, identity, and inheritance than about how whiskey is made. I don’t really give a shit what the barrel proof is, you know what I mean? I don’t know if you saw Springsteen’s Broadway show, but at one point, he talked about the difference between being an ancestor to your children or a ghost. I wanted this to be a book about the things we inherit, what we choose to pass on, what we owe those who came before, what we owe those who come after, and how all of those things intersect and diverge. This book could have been about John McPhee’s birch-bark canoe maker. Ultimately, it’s about the concept of craft.

So why bourbon? Are you a fan? Do you buy $300 bottles of Pappy?

I have bought $300 bottles of Pappy, but not often. I was always a bourbon drinker, but I’m not a student; I’ve never been on a bourbon message board in my life. But it was my drink of choice. I had met Julian at a party in Atlanta, and liked him, and I liked his son, Preston. And I realized that I was truly interested in how these people did it—how what they were creating was a reflection of them. It wasn’t just about bourbon.

It comes back to craft, then, which seems rare in our modern corporate economy. Given that, what is your outlook for the future of Pappy and other craft-driven products?

What’s interesting is that the amount of capital it takes to make good whiskey is pretty staggering. A craft maker doesn’t necessarily make a better product than a really great master distiller for a huge company. There’s a myth that somehow the small-time guy in the woods is making better whiskey. These guys that are doing tremendous quantities of whiskey, their “white dog” off of the still [raw, clear un-aged whiskey before it is barreled] is incredible. I guess the larger question is, what can we learn about the present and future of America by following these trend patterns—and circular returns in popularity—of various craft products?

It’s clear that this book was a journey for you as much as it will be for readers.

Yes. If you go down the rabbit hole of the history of bourbon, you end up accidentally catching a glimpse of these big, tectonic, essential truths about the American idea and history. I think you can find significant elements of American history in that bottle. And that was really exciting, because that wasn’t intentional. I discovered things that I couldn’t have set off looking for. There was nothing rote or paint-by-the-numbers about the process. I took it section by section, and I could feel the story taking me somewhere. It felt alive, like it was taking me to a destination that I didn’t know existed.

Were there times when you thought that it wasn’t going to work and you would have to move on to something else?

Well, I put out another book in the middle of this [The Cost of These Dreams], and that wasn’t an accident. You can read those tea leaves however you would like, but this was three or four years in the making. I had false starts, times where I would write 8,000 words and think, this sucks. I couldn’t figure out the voice at first. Where is a narrator? Where do I stand in relationship to Julian?

What’s your relationship like with Julian now? Do you talk often?

Not a lot. What’s left? It’s all in the book [laughs]. Julian is lovely. If something was going wrong in my life, I would call him. He’s such a steady, reasonable, ethical person; you just want his take on stuff. I don’t always agree with his view, but it’s always well considered.

Along your journey, you consulted the work of Kentucky native Thomas Merton, the well-known theologian, monk, and ethicist. Tell me about that.

Reading him was the closest I’ve been to really believing there’s a God in a long time; it was that transformative. I don’t want to be overwrought and ham-fisted. It didn’t change my life, but it made me consider all sorts of things that I wasn’t before I went on this journey. In some very narcissistic part of my brain, I hope that if anything else, this book is sort of a travel companion as people think about these things in their own lives. I want it to be more than just a vehicle to learn about Julian or to hear my story, a way for people who are dealing with these things that Julian and I are dealing with to feel like somebody is walking there with them.

Eric Liebetrau is the nonfiction and managing editor.