There’s something comforting about lighting up a cigar and talking politics, sports, and the decline of the American empire from the cozy haze of The Chicago Smokehouse. This week, as we puffed on a (possibly illegal) Cuban Cohiba and discussed everything from press box etiquette to presidential posturing, one thing became abundantly clear: whether it’s taxes, tariffs, or the return of Erik the Red, the smoke is getting thicker.

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This week on The Chicago Smokehouse, John Howell and Rick Telander dive into the billion-dollar business of college athletics—and the increasingly blurry line between amateurism and professionalism.

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Big John Howell and Rick Telander light up cigars—and history—as they crack open one of the wildest sports stories of the 20th century: the short-lived, long-mythologized United States Football League (USFL). With the help of Jeff Pearlman’s book Football for a Buck: The Crazy Rise and Crazier Demise of the USFL, the conversation goes far beyond X’s and O’s, veering into locker rooms, courtrooms, and even the White House.

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After nearly three decades as one of Chicago’s most distinctive voices in sports journalism, Rick Telander is moving on from the Chicago Sun-Times. The longtime columnist and Sportswriters Hall of Fame member announced that he has accepted a buyout from the newspaper. The episode, co-hosted with self-described “almost broadcast legend” John Howell, was equal parts reflection, frustration, and humor—an impromptu farewell from one of the city’s most revered writers who insists he’s not fading away, just turning the page.

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Sports writer John Feinstein has passed away at 69. Rick Telander shares personal anecdotes and insights about Feinstein's impact on sports journalism, his relationships with notable figures like Bobby Knight, and the art of storytelling in sports writing. The discussion also touches on the evolution of journalism, the importance of rooting for the underdog, and the personal reflections that arise from the loss of a colleague.

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Rick Telander shares his experiences with Mike Ditka, reflecting on their collaboration for the book 'In Life, First You Kick Ass.' The discussion covers personal anecdotes, the legacy of the 1985 Bears, and the intense culture of football during that era. Telander provides insights into Ditka's personality, the challenges of writing the book, and the impact of injuries on players. The conversation also touches on the evolution of football culture and the lessons learned from Ditka's life and career.

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John Howell and Rick Talender delve into the world of sports journalism, the evolution of sports talk radio, and Talender's personal journey from being drafted by the Kansas City Chiefs to becoming a prolific author. They discuss the dynamics of coaching, the legacy of the Chiefs, and the representation of race in football, all while reflecting on the lessons learned from Talender's memoir, 'Like a Rose.'

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Some conversations feel like a front-row seat to history. Others feel like stepping into a smoke-filled backroom where legends swap stories over a cigar. When John Howell sits down with Chicago Sun-Times sports columnist and author Rick Telander, you get both.

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