The Tony Soprano of Bourbon episode artwork

EPISODE · Mar 18, 2025 · 48 MIN

The Tony Soprano of Bourbon

from The Bourbon Playbook

This week, we’re diving into the history of one of the most notorious figures in bourbon—and crime—history. Before Prohibition, he was a respected lawyer. During it, he became the “King of the Bootleggers,” controlling nearly a third of all illegal liquor in the U.S.His story is filled with fortune, betrayal, and even murder. And now, his legacy lives on in a high-proof bourbon that’s just as bold as his past. Join the guys as they break down the rise, fall and redemption of this whiskey legend — and, of course, give their takes on whether his namesake bourbon is worth the hype. Grab a glass, because this pour comes with one hell of a backstory! Support the pod: tbplaybook.com

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The Tony Soprano of Bourbon

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This episode is 48 minutes long.

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This episode was published on March 18, 2025.

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This week, we’re diving into the history of one of the most notorious figures in bourbon—and crime—history. Before Prohibition, he was a respected lawyer. During it, he became the “King of the Bootleggers,” controlling nearly a third of all illegal...

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