Chicago Way w/John Kass (11/17/25): Paul Vallas is here to talk about his latest column- “Chicago’s Killing Fields”, Mayor Brandon Johnson’s awful policies, and the time he played the role of Barney. Plus, Kasso remembers his time in the saddle and a good horse.

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Chicago Way w/John Kass (11/11/25): Chicago Ald. Ray Lopez (15th) is here to explain his amnesty plan to John Kass & Jeff Carlin and discuss why he’s not surprised Chuy Garcia used old-school machine politics to retire on another public pension and coronate his ‘Leftino” successor. Plus, Kasso welcomes Kribi Coffee into the fold.

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Chicago Way w/John Kass (11/03/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin this week to discuss what Zohran Mamdani’s role as a leader of the modern Democratic Party will look like, how the U.S. is going to respond to the situation in Nigeria, when things went wrong for William F. Buckley, and who is to blame for those stupid ads you keep getting about diapers. Plus, Kass wonders if a single smile can bring down an entire city?

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Chicago Way w/John Kass (10/28/25): This week, John Kass & Jeff Carlin wax philosophically about how the U.S. found itself in revolutionary times and where do we go from here. Plus, Kasso wonders if New York is ready for what it’s voting for?

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Chicago Way w/John Kass (10/20/25): RealClear Politics’ Tom Bevan is here with a post-op on what impact the “No Kings” rallies (Chicago’s rally featured one of Illinois’ top gamblers -Gov. JB Pritzker (D), for whom Tom has a some choice words) will have, why he thinks this government shutdown will break the 2018-2019 shutdown record of 35 days, and who he thinks will control New York City & State if democratic socialist Zohran Mamdani becomes leader of the Big Apple. Plus, Kasso wonders if the art of the follow-up question to public officials is dead?

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Chicago Way w/John Kass (10/13/25): This week, Garry McCarthy – former Chicago Police Department (CPD) Superintendent and current Chief of Police for Willow Springs, IL- joins John Kass and Jeff Carlin to discuss a disturbing dispatch call involving CPD, Customs and Border Protection (CBP), Immigration and Customs Enforcement (ICE), Cook County Sheriffs, & Illinois State Police in Broadview, and lessons from hosting the United Nations convention in 2012 McCarthy might be useful today. McCarthy also reflects on the role data plays in policing and what Chicago could do better. Plus, Kass wonders if Illinois’ poorly written laws are only written that way to serve the Democratic leadership and serve only to obfuscate the true intentions of the city and state’s power machine?

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Chicago Way w/John Kass (10/06/25): Fall is officially here and so is story time. John Kass tells Jeff Carlin about standing outside Wrigley Field in 1984 and the series of events that lead him there. Plus, Kasso gets an apology.

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Chicago Way w/John Kass (09/29/25): This week, the Honorable Judge James R. Brown (ret.) joins John Kass & Jeff Carlin to talk about the moment soon-to-be-former Chief Judge Timothy Evans gathered bond court judges to direct them to go against the rule of law and let violent offenders off easy, lest the judges be reassigned. Plus, Kasso wonders if Patrick Fitzgerald can save James Comey from his alleged lies?

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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, is this week’s guest joining John Kass & Jeff Carlin with a breakdown of the FCC meddling in the Jimmy Kimmel fiasco and what it will take to push the JB Pritzkers of the world out of politics. Plus, Kasso wonders if we’re ready to deal with a post-Charlie Kirk world?

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Chicago Way w/John Kass (09/15/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin to talk about the cold-blooded murder of Charlie Kirk and how free speech in the UK is under threat. Plus, Kasso wonders if the Democrat culture of assassination can be stopped?

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