On this edition of What We’re Drinking with Dan Dunn, Dan sits down with writer, cultural agitator, and longtime professional pundit Joel Stein for a conversation that cuts straight through wine, journalism, mortality, and modern American weirdness.

Dan and Joel talk frankly about the sad, shrinking state of journalism. What it used to be, what it’s become, and why so many writers now find themselves operating outside the old institutions, whether they planned to or not. That leads naturally to a discussion of the recent death of Scott Adams, and Joel’s clear-eyed, unsentimental piece on Adams for The New York Times, a meditation on talent, provocation, and what happens when a cultural figure spends years daring the world to turn on him.

The conversation turns darker with news that the investigation into Hunter S. Thompson’s death has been reopened. Dan, who was friends with Hunter for years, offers his own perspective—measured, personal, and skeptical—on what reopening the case means, what it doesn’t, and why some legends refuse to stay buried no matter how definitive the ending once seemed.

Dan also runs through his favorite cities to drink in across America. Places where bars still feel lived-in and drinks are poured with conviction. And, in a moment of humility rarely captured on tape, he admits to losing a football bet to Braiden Albrecht of Mayacamas Vineyards, proving once again that confidence and gambling are distant cousins at best.

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