Chicago Way w/John Kass (12/15/25): Austin Berg, Executive Director of the Chicago Policy Center at the Illinois Policy Institute, join John Kass & Jeff Carlin with a look at just how badly Mayor Brandon Johnson has managed Chicago’s finances and the inane ideas the Mayor has come up with to fill a nearly $1.2 billion budget gap for 2026, like a corporate head tax. Plus, Kasso remembers the time his good friend, the dearly departed, Bruce Dold taught him a lesson about Chicago: You always attend a wake.

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Chicago Way w/John Kass (12/08/25): Pastor Corey Brooks joins John Kass & Jeff Carlin to discuss how his fundraising effort to walk across the entire United States in a year is going, why he has zero confidence in Chicago Mayor Brandon Johnson, what former mayor Daley said to him, and where he’s been eating along the journey to raise money for ProjectHOOD. Plus, Kasso wonders what President ‘Drone Kill’ Obama really thinks about recent attacks in the Caribbean.

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Chicago Way w/John Kass (12/01/25): This week, retired Police Chief, Tom Weitzel (Riverside), joins John Kass & Jeff Carlin to talk about who is to blame for the release of veteran convict Lawrence Reed –who allegedly poured gasoline over 26-year-old Bethany MaGee at random, setting her on fire aboard a Blue Line train– and what should have been done to prevent this incident. Chief Weitzel also discusses how reforms to the ‘SAFE-T Act’ can improve the judicial system, where the future of electronic monitoring is headed, and his substack -‘The Memo.’ Plus, Kasso wonders if Governor JB Pritzker & Chicago Mayor Brandon Johnson really believe this was an ‘isolated incident?’

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Chicago Way w/John Kass (11/24/25): Thanksgiving is upon us, but senseless violence continues to plague the city, and John Kass wonders if the judges who let career violent criminals back on the street to destroy more lives will ever be held accountable? Kasso is thankful for a good cup of Kribi Coffee and supports their efforts to improve the city.

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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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