Episodes

  • Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016

    Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016
    Jun 22 2026
    Chicago Way w/John Kass (06/22/26): Re-Issue: Episode #6 from 02/10/206. Cartoonist Scott Stantis joins John Kass & Jeff Carlin to discuss what turns out to be the end of Rahm Emanuel’s tenure as Chicago Mayor, the 2016 primary season featuring Hillary Clinton vs. Bernie Sanders & Donald Trump vs. establishment everything, and meet two drivers […]
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    Less than 1 minute
  • Chicago Way w/John Kass: What we don’t talk about says a lot

    Chicago Way w/John Kass: What we don’t talk about says a lot
    Jun 15 2026
    Chicago Way w/John Kass (06/15/26): John Kass & Jeff Carlin are together to talk about the things we don’t talk about when violence happens, how Chicago Democrats let the Bears go to Indiana to save face, and why the Obama Presidential Center allegedly owes people money, already. Plus, Kasso remembers the first time meeting his […]
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    Less than 1 minute
  • Chicago Way w/John Kass: Reissue – Episode #1 from January of 2016

    Chicago Way w/John Kass: Reissue – Episode #1 from January of 2016
    Jun 8 2026
    Chicago Way w/John Kass (06/08/26): John is off this week, celebrating his son’s wedding, so we bring you a reissue from January of 2016. The first episode, featuring John Kass, Will Lee, and Jeff Carlin, talking about a strange hat controversy at a local TV station, bizarre news stories on TV, Will’s amazing story about […]
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  • Chicago Way w/John Kass: Does Mayor Brandon Johnson even want to run again?

    Chicago Way w/John Kass: Does Mayor Brandon Johnson even want to run again?
    May 31 2026
    Chicago Way w/John Kass (05/31/26): Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin with questions about Chuy Garcia’s old school political tactics, whether or not Brandon Johnson has the heart to run for re-election, and why his fellow alders are finally getting behind his proposal to hold parents of violent teens accountable? Also, […]
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    Less than 1 minute
  • Chicago Way w/John Kass: Summer is for the brave

    Chicago Way w/John Kass: Summer is for the brave
    May 26 2026
    Chicago Way w/John Kass (05/26/26): John Kass & Jeff Carlin celebrate the bravery it takes to face violent warm summer nights in Chicago in the face of gang wars and ‘teen takeovers.’ Plus, Kasso has a ‘Happy’ pet peeve. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by using […]
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  • Chicago Way w/John Kass: Don’t (bleep) with a pit bull’s reputation

    Chicago Way w/John Kass: Don’t (bleep) with a pit bull’s reputation
    May 18 2026
    Chicago Way w/John Kass (05/18/26): John Kass & Jeff Carlin are joined by former (possibly, future?) candidate for Mayor of Chicago, head of the public school systems in Chicago, Philadelphia and the Louisiana Recovery School District, Paul Vallas to talk about recent attacks on him, who he thinks might be behind it, and what he […]
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    Less than 1 minute
  • Chicago Way w/John Kass: Hopium and the well-dressed chili powder thief

    Chicago Way w/John Kass: Hopium and the well-dressed chili powder thief
    May 11 2026
    Chicago Way w/John Kass (05/11/26): John Kass & Jeff Carlin remember his late mother, Betty Kass, and as she would have wanted, move on to the ugly Obama Presidential Center building, Chicago alders wanting Walgreens to be criminally charged for closing stores, and Stephen Colbert smirking his way through a farce of an interview with […]
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  • Chicago Way w/John Kass: ‘Tips’ for Mother’s Day

    Chicago Way w/John Kass: ‘Tips’ for Mother’s Day
    May 4 2026
    Chicago Way w/John Kass (05/05/26): On this episode, revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin to discuss how tipping became an american tradition and what it means to the industry. Plus, Kasso wonders if there is a trick to surviving Mother’s Day at a restaurant? Follow Everything John Kass – JohnKassNews.com […]
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    Less than 1 minute