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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Featured image for “Chicago Way w/John Kass: Dead people voting, flooded basements, and The Nice Man”

Chicago Way w/John Kass: Dead people voting, flooded basements, and The Nice Man

Chicago Way w/John Kass (07/28/25): This week, Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin to discuss how Mayor…

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Featured image for “The Chicago Way w/John Kass: A wake-up call for NYC from the Windy City”

The Chicago Way w/John Kass: A wake-up call for NYC from the Windy City

Chicago Way w/John Kass (07/21/25): On this episode, Ted Dabrowski of Wirepoints.com joins John Kass & Jeff Carlin to highlight…

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Featured image for “Chicago Way w/John Kass: Is MAGA bigger than Trump?”

Chicago Way w/John Kass: Is MAGA bigger than Trump?

Chicago Way w/John Kass (07/14/25): Continuing the conversation with Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus…

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Featured image for “Chicago Way w/John Kass: Freedom rings”

Chicago Way w/John Kass: Freedom rings

Chicago Way w/John Kass (07/07/25): Charles Lipson joins John Kass & Jeff Carlin for this post Independence Day episode. Charles…

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Featured image for “Chicago Way w/John Kass: On the road at the Sicilian Summer Block Party”

Chicago Way w/John Kass: On the road at the Sicilian Summer Block Party

Chicago Way w/John Kass (06/30/25): On a HOT summer Sunday, John Kass & Jeff Carlin head out to the first…

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Featured image for “The Chicago Way w/John Kass: Business as usual means someone else’s hand in you pocket”

The Chicago Way w/John Kass: Business as usual means someone else’s hand in you pocket

Chicago Way w/John Kass (06/23/25): On this episode, revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin with…

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Featured image for “Chicago Way w/John Kass: Straight from the butcher’s mouth”

Chicago Way w/John Kass: Straight from the butcher’s mouth

Chicago Way w/John Kass (06/16/25): This week, John Kass & Jeff Carlin are pleased to welcome Sal Camarda from Joseph’s…

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Featured image for “Chicago Way w/John Kass: The 80/20 problem”

Chicago Way w/John Kass: The 80/20 problem

Chicago Way w/John Kass (06/09/25): Prof. Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of…

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Featured image for “Chicago Way w/John Kass: Old age and doing time”

Chicago Way w/John Kass: Old age and doing time

Chicago Way w/John Kass (06/02/25): This week, John Kass & Jeff Carlin discuss the merits of President Donald Trump commutating the…

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Featured image for “The Chicago Way w/John Kass: Eeyore in the city”

The Chicago Way w/John Kass: Eeyore in the city

Chicago Way w/John Kass (05/27/25): This week, John Kass tries to get to the bottom of Jeff Carlin’s bad mood by…

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Featured image for “Chicago Way w/John Kass: The cover-up of Biden’s health is a scandal that can’t be ignored”

Chicago Way w/John Kass: The cover-up of Biden’s health is a scandal that can’t be ignored

Chicago Way w/John Kass (05/19/25): RealClear Politics’ Tom Bevan is here to discuss James Comey selling seashells by the seashore and what…

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Featured image for “Chicago Way w/John Kass: Alder pulls back the curtain on Mayor Johnson’s patronage scheme”

Chicago Way w/John Kass: Alder pulls back the curtain on Mayor Johnson’s patronage scheme

Chicago Way w/John Kass (05/12/25): This week, Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin to look at…

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Featured image for “Chicago Way w/John Kass: When the oligarchs run the show, the people lose”

Chicago Way w/John Kass: When the oligarchs run the show, the people lose

Chicago Way w/John Kass (05/05/25): This week, former CEO of the Chicago Public Schools (1995-2001) & candidate for mayor, Paul…

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Featured image for “Chicago Way w/John Kass: Sounds like JB Pritzker is ready for a donnybrook”

Chicago Way w/John Kass: Sounds like JB Pritzker is ready for a donnybrook

Chicago Way w/John Kass (04/29/25): On this edition, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast,…

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