Chicago Way w/John Kass (07/07/26): Happy Birthday America! Charles Lipson joins John Kass & Jeff Carlin for a look at who is pushing the narrative that the US is bad, why people can’t seem to agree on common sense anymore, and what is at risk if we dismantle institutions like the Constitution. Charles is Professor Emeritus of Political Science at University of Chicago and you can read him at CharlesLipson.com Plus, Kasso is wonders if anyone noticed Chicago Police Supt. Larry Snelling fleeing the sinking ship that is Mayor Brandon Johnson’s tenure?

Chicago Way w/John Kass (06/30/26): John Kass & Jeff Carlin are back this week to dive into what the current state of American culture means to the rest of the world, how failures that stack up when we elect/hire/listen to unqualified leaders, and a stack of questions from listeners. Plus, Kasso is VERY confident the USMNT will win it all at FIFA World Cup.

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 of the famous Oscar Meyer Wienermobile. Plus, Kasso reads his column about courting his lovely bride, Betty.

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 former legman, Will ‘Old School’ Lee, covering a murder.

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 life on the South Side of Chicago, and Rahm Emanuel’s never-ending headache. Plus, John tells the story of the first time he was burned by a lying witness.

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, Ald. Lopez can’t explain why Mayor Brandon Johnson would give Pope Leo a Cubs hat, but Ray knows why he’s running for re-election in the 15th ward. Plus, Kasso wonders if Indiana should change the state slogan to ‘FAFO?’

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.

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 aims to do about it. Plus, Kasso wonders if those in the know are ready for when the pit bull jumps the fence?

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 former-President Obama. Plus, Kasso tells the story of the well-dressed chili powder thief.

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?