Finding the Heart of the Van Winkle Family Legacy: A Book Review of Pappyland

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Pappy Van Winkle bourbon has indisputably become an iconic symbol of the American good life. Prominently featured in contemporary film, literature, and music, gifted on special occasions, and toasted at celebrations, love it or hate it, the brand has assumed cult status in American drinking culture — with all the baggage that entails. People who don’t drink, or at least don’t drink bourbon, can easily recognize Pappy as a hallmark of quality, in much the same way someone who’s not into cars knows that Ferraris are fast and cool.

But like any cultural obsession, reality is simplified, objectified, and commercialized. After a while, it’s not about the exceptional whiskey, it’s about the status and scarcity — the prize. In Pappyland: A Story of Family, Fine Bourbon, and the Things that Last, Wright Thompson cuts through the exuberance with a very human story about the people, places, and connections that led to what Pappy Van Winkle Bourbon is today.

Thompson offers an intimate, beautifully nostalgic journey through moments of the Van Winkle legacy, guided by and through Thompson’s friendship with Julian Van Winkle III. Thompson is unafraid to plunge into uncomfortable areas and conjure ghosts of the past that some may have preferred to stay buried. The moments between Thompson and Van Winkle III are honest and introspective, and there is a real feeling of the book organically unfolding. 

Weaving a parallel narrative between Van Winkle’s complicated relationship with his father, Julian Van Winkle II, and the author’s relationship with his own father (and his anxiety about becoming a father himself), Thompson dissects the past and present, as he accompanies Van Winkle III to bourbon gatherings and on family vacations. Pappyland fills in the cracks of the Van Winkle family story with context from memories and lived experience, bringing the characters and legendary whiskey to life in a way not previously done.  

Julian Van Winkle II is generally blamed for losing the family’s Stitzel-Weller distillery in 1972 — but it’s complicated. Tastes had changed and times were tough for bourbon. Pappyland is inescapably about a third-generation distiller living in the shadow of his father and grandfather’s legacy and the burden of an instantly recognizable family name, but it is also about how Van Winkle III, through sheer determination and grit, wagered everything to rebuild the family dynasty. 

Van Winkle III is one of the only people on the planet who really knows how Pappy is supposed to taste. Though some clever marketing was involved at key junctures along the line, Van Winkle III brilliantly navigated numerous obstacles to create the Pappy we know today in partnership with Buffalo Trace Distillery. Pappyland makes many familiar stops along the way, such as Julian P. “Pappy” Van Winkle, Sr.’s start as a traveling salesman for W.L. Weller and his purchase of the Stitzel distillery, but the perspective from Van Winkle III is absolutely new.

Thompson writes a deeply human and very readable portrait of bourbon royalty and a man, Van Winkle III, who has achieved rockstar status. Both showman and humble family man, by the end of the book, you feel you really understand the man who has become a legend in his own time.  

Pappyland is elegant and surprising. Don’t expect a blow-by-blow account of the Van Winkle family history. This is a book about people, feelings, and friendships, and reads like a purposeful stroll through the hills of Kentucky. Whether it’s aged 15 years or 23 years, Pappy bourbon has a magical allure that has gripped the popular imagination. Thompson has captured this magic perfectly in Pappyland with a warm and heartfelt narrative about Boubron’s most famous family name.

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