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  • Chicago Way w/John Kass: Clean up on aisle GOP…

    Chicago Way w/John Kass: Clean up on aisle GOP…
    9 Nov 2026
    Chicago Way w/John Kass (11/09/26): This week Tom Bevan, the president and co-founder of RealClearPolitics, joins John Kass & Jeff Carlin to break down the massive political shakeup of the 2026 midterm elections.Together, they analyze the “blue wave” that swept the country, leaving the Republican Party in absolute shambles. From James Tallarico’s shocking victory in […]
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  • Chicago Way w/John Kass: ‘White Guilt: A Documentary Essay’

    Chicago Way w/John Kass: ‘White Guilt: A Documentary Essay’
    19 Oct 2026
    Chicago Way w/John Kass (10/19/26): Dr. Carrie Mendoza joins John Kass & Jeff Carlin this week to talk about New Trier Neighbors (NTN) screening of ‘White Guilt: A Documentary Essay’ on Nov. 5th with a special guest panel that includes the film’s director at New Trier High School. Beyond working in emergency medicine, Dr. Mendoza […]
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  • Chicago Way w/John Kass: The end of an era — From Michigan Avenue to Ep. 566

    Chicago Way w/John Kass: The end of an era — From Michigan Avenue to Ep. 566
    26 Oct 2026
    Chicago Way w/John Kass (10/26/26): John Kass announced that John Kass News is winding down. Facing five strokes over three years, John is hanging up the spear: “I can’t do another one… We’re winding down now, and we know it’s time.” On this week’s episode of The Chicago Way, John and Jeff Carlin take a […]
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  • Chicago Way w/John Kass: The gunshot detection quagmire and the battle for city council

    Chicago Way w/John Kass: The gunshot detection quagmire and the battle for city council
    2 Nov 2026
    Chicago Way w/John Kass (11/02/26): In this episode of The Chicago Way, John Kass and Jeff Carlin are joined by Alderman Raymond Lopez of the 15th Ward to dissect the shifting dynamics, high-stakes budgets, and political maneuvers inside Chicago’s City Council. Fresh off securing an unopposed run for his seat in the 2027 election, Alderman […]
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  • Chicago Way w/John Kass: A hooley of a good time

    Chicago Way w/John Kass: A hooley of a good time
    21 Sep 2026
    Chicago Way w/John Kass (09/21/26): Mike ‘Houli’ Houlihan joins John Kass & Jeff Carlin to talk about his recent column on JohnKassNews.com and the 12th Annual Irish American Movie Hooley film festival. Plus, Kasso tells the story about his career being launched by parade queen. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin […]
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  • Chicago Way w/John Kass: When good food is simple, what more do you need?

    Chicago Way w/John Kass: When good food is simple, what more do you need?
    28 Sep 2026
    Chicago Way w/John Kass (09/28/26): Revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin to discuss his recent visit to Greece, the foods scene there, and what he thinks every restaurant should do to insure people come back. Plus, Kasso questions why some places put a clown show to impress? Follow Everything John […]
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  • Chicago Way w/John Kass: The time is now for independent media in Illinois

    Chicago Way w/John Kass: The time is now for independent media in Illinois
    5 Oct 2026
    Chicago Way w/John Kass (10/05/26): On this episode, author and retired director of medical intensive care at Cook County Hospital in Chicago for over 20 years Dr. Cory Franklin joins John Kass & Jeff Carlin to discuss the need for independent media in Chicago and what it was like working with editors who pushed hard […]
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  • Chicago Way w/John Kass: Chicago Flips Red’s candidate for mayor

    Chicago Way w/John Kass: Chicago Flips Red’s candidate for mayor
    8 Sep 2026
    Chicago Way w/John Kass (09/07/26): Co-founder of ‘Chicago Flips Red’ Danielle Carter-Walters joins John Kass & Jeff Carlin to talk about why she is running for mayor, how she was motivated has been burned by the city, and what it takes to stand up to people in her own community. Plus, Kasso wonders if mainstream […]
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