The Chicago Way Podcast
1) Chicago Way w/John Kass: Over 50 shot this weekend, but we don’t need help
Chicago Way w/John Kass (09/01/25): This week, former Cook County and federal prosecutor Bob Milan joins John Kass & Jeff Carlin to talk about his original plan from 10 years ago to bring in Nati...Show More
2) Chicago Way w/John Kass: When IL Dems play Russian roulette with our children
Chicago Way w/John Kass (08/25/25): Glenview native Joe Abraham joins John Kass & Jeff Carlin to talk about his gut-wrenching experience losing his daughter Katie when she was killed in a hit-and...Show More
3) Chicago Way w/John Kass: The iron triangle of deception
Chicago Way w/John Kass (08/18/25): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin with a look at how President Barack Obama’s misdeeds compare to Richard Nixon, what can...Show More
4) Chicago Way w/John Kass: Obama, Pritzker, and the stories they tell
Chicago Way w/John Kass (08/11/25): This week, John Kass & Jeff Carlin tackle JB Pritzker’s hypocrisy when it comes gerrymandering, evidence that President Barack Obama was trying to convin...Show More
5) 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 circulating petitions and seriously considering running against Cook ...Show More
6) 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 Brandon Johnson has let flooding plague the city, year after year, while he...Show More
7) 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 how Governor JB Pritzker is delusional about Illinois’ status...Show More
8) 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 is the Peter B. Ritzma Professor of Political Science Emeritus at ...Show More
9) 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 annual Sicilian Summer Block Party in the Dunning neighborhood to break bread and enjoy s...Show More
10) 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 a look at the history of the ‘Chicago Way’ -alderman...Show More