Featured image for “The Chicago Way w/John Kass: A smile to bring down a city”

The Chicago Way w/John Kass: A smile to bring down a city

Chicago Way w/John Kass (11/03/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago,…

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Featured image for “Chicago Way w/John Kass: Revolutionary times”

Chicago Way w/John Kass: Revolutionary times

Chicago Way w/John Kass (10/28/25): This week, John Kass & Jeff Carlin wax philosophically about how the U.S. found itself…

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Featured image for “The Chicago Way w/John Kass: “No Kings” rallies and Pritzker’s gambling habits”

The Chicago Way w/John Kass: “No Kings” rallies and Pritzker’s gambling habits

Chicago Way w/John Kass (10/20/25): RealClear Politics’ Tom Bevan is here with a post-op on what impact the “No Kings”…

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A Busy Week

Dear readers, I wanted to send you all a quick email to let you know that my next new column…

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Featured image for “The Chicago Way w/John Kass: Chaos Reigns Over Local LEO/FED Interactions Almost By Design”

The Chicago Way w/John Kass: Chaos Reigns Over Local LEO/FED Interactions Almost By Design

Chicago Way w/John Kass (10/13/25): This week, Garry McCarthy -former Chicago Police Department (CPD) Superintendent and current Chief of Police for…

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Featured image for “The Chicago Way w/John Kass: An origin story”

The Chicago Way w/John Kass: An origin story

Chicago Way w/John Kass (10/06/25): Fall is officially here and so is story time. John Kass tells Jeff Carlin about standing…

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Featured image for “Chicago Way w/John Kass: A retired judge on how a bad apple can spoil the bunch”

Chicago Way w/John Kass: A retired judge on how a bad apple can spoil the bunch

Chicago Way w/John Kass (09/29/25): This week, the Honorable Judge James R. Brown (ret.) joins John Kass & Jeff Carlin to…

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Featured image for “The Chicago Way w/John Kass: What the FCC’s Carr got wrong about Jimmy Kimmel”

The Chicago Way w/John Kass: What the FCC’s Carr got wrong about Jimmy Kimmel

Chicago Way w/John Kass (09/22/25): Dan Proft, co-host of “The Morning Answer” radio program 5-9 a.m. on WIND AM 560,…

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Featured image for “Chicago Way w/John Kass: Where do we go from here?”

Chicago Way w/John Kass: Where do we go from here?

Chicago Way w/John Kass (09/15/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago,…

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Featured image for “The Chicago Way w/John Kass: Illinois voters have a clear choice for their future”

The Chicago Way w/John Kass: Illinois voters have a clear choice for their future

Chicago Way w/John Kass (09/01/25): Newly minted candidate for Illinois Governor, Ted Dabrowski of Wirepoints joins John Kass & Jeff…

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Featured image for “The Chicago Way w/John Kass: When Democrats are pro criminal, the children lose”

The Chicago Way w/John Kass: When Democrats are pro criminal, the children lose

Chicago Way w/John Kass (09/01/25): This week, former Cook County and federal prosecutor Bob Milan joins John Kass & Jeff…

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Featured image for “Chicago Way w/John Kass: When IL Dems play Russian roulette with our children”

Chicago Way w/John Kass: When IL Dems play Russian roulette with our children

Chicago Way w/John Kass (08/25/25): Glenview native Joe Abraham joins John Kass & Jeff Carlin to talk about his gut-wrenching…

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Featured image for “The Chicago Way w/John Kass: The Iron Triangle of Deception”

The Chicago Way w/John Kass: The Iron Triangle of Deception

Chicago Way w/John Kass (08/18/25): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin with a look…

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Featured image for “Chicago Way w/John Kass: Obama, Pritzker, and the stories they tell”

Chicago Way w/John Kass: Obama, Pritzker, and the stories they tell

Chicago Way w/John Kass (08/11/25): This week, John Kass & Jeff Carlin tackle JB Pritzker’s hypocrisy when it comes gerrymandering,…

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Featured image for “Chicago Way w/John Kass: Ald. Reilly leading the way for ‘closet moderates’ against Preckwinkle”

Chicago Way w/John Kass: Ald. Reilly leading the way for ‘closet moderates’ against Preckwinkle

Chicago Way w/John Kass (08/04/25): Chicago Alderman Brendan Reilly (42nd) joins John Kass & Jeff Carlin to announce that his…

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