The Chicago Way

Chicago Way w/John Kass (11/09/26): This week Tom Bevan, the president and co-founder of RealClearPolitics, joins John Kass & Jeff Carlin to break down the massive political shakeup of the 2026 midterm elections. Together, they analyze the “blue wave” that swept the country, leaving the Republican Party in absolute shambles. From James Tallarico’s shocking victory in […]

Chicago Way w/John Kass (11/02/26): In this episode of The Chicago Way, John Kass and Jeff Carlin are joined by Alderman Raymond Lopez of the 15th Ward to dissect the shifting dynamics, high-stakes budgets, and political maneuvers inside Chicago’s City Council. Fresh off securing an unopposed run for his seat in the 2027 election, Alderman […]

Chicago Way w/John Kass (10/26/26): John Kass announced that John Kass News is winding down. Facing five strokes over three years, John is hanging up the spear: “I can’t do another one… We’re winding down now, and we know it’s time.” On this week’s episode of The Chicago Way, John and Jeff Carlin take a […]

Chicago Way w/John Kass (10/19/26): Dr. Carrie Mendoza joins John Kass & Jeff Carlin this week to talk about New Trier Neighbors (NTN) screening of ‘White Guilt: A Documentary Essay’ on Nov. 5th with a special guest panel that includes the film’s director at New Trier High School. Beyond working in emergency medicine, Dr. Mendoza […]

Chicago Way w/John Kass (10/05/26): On this episode, author and retired director of medical intensive care at Cook County Hospital in Chicago for over 20 years Dr. Cory Franklin joins John Kass & Jeff Carlin to discuss the need for independent media in Chicago and what it was like working with editors who pushed hard […]

Chicago Way w/John Kass (09/28/26): Revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin to discuss his recent visit to Greece, the foods scene there, and what he thinks every restaurant should do to insure people come back. Plus, Kasso questions why some places put a clown show to impress? Follow Everything John […]

Chicago Way w/John Kass (09/21/26): Mike ‘Houli’ Houlihan joins John Kass & Jeff Carlin to talk about his recent column on JohnKassNews.com and the 12th Annual Irish American Movie Hooley film festival. Plus, Kasso tells the story about his career being launched by parade queen. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin […]

Chicago Way w/John Kass (09/14/26): John Kass & Jeff Carlin react to Mayor Brandon Johnson announcing his re-election campaign with pointed attacks aimed at AIPAC and billionaire Chicago financier Michael Sacks. Plus, Kasso tells the tale of the 40 flies. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by […]

Chicago Way w/John Kass (09/07/26): Co-founder of ‘Chicago Flips Red’ Danielle Carter-Walters joins John Kass & Jeff Carlin to talk about why she is running for mayor, how she was motivated has been burned by the city, and what it takes to stand up to people in her own community. Plus, Kasso wonders if mainstream […]

Chicago Way w/John Kass (09/01/26): Thom Serafin, long-time political strategist, Communicator in Chief of Serafin & Associates, and newly collaborating with Mercury Illinois, joins John Kass & Jeff Carlin to talk about the race for mayor, his lunch with Fidel Castro, and whether or not the Bears will ever get a stadium built. Plus, Kasso […]

Chicago Way w/John Kass (08/24/26): Dan Proft, co-host of “The Morning Answer” radio program 5-9 a.m. on WIND AM 560, joins John Kass & Jeff Carlin to discuss how he’s getting blamed for the demise of the Republican party in Illinois for some reason, what happens when Illinois Democrats realize the whole system is collapsing […]

Chicago Way w/John Kass (08/17/26): Businessman and philanthropist Willie Wilson joins John Kass & Jeff Carlin to talk about why he wants to run for Chicago mayor again, who he thinks is ‘mentally ill’ for questioning his reasons, and what he thinks about people running for two offices at once. Plus, Kasso wonders if Michael […]

Chicago Way w/John Kass (08/10/26): Charles Lipson is back, joining John Kass & Jeff Carlin to discuss why ‘democratic socialism’ is on the rise in the United States, who is pushing this shift within the Democratic Party, and what it means for the future of the republic. Charles is the Peter B. Ritzma Professor of […]

Chicago Way w/John Kass (08/03/26): This week, Dr. Cory Franklin – who spend over 25 years at Cook County Hospital in Chicago, joins Jeff Carlin to make sense of what Dr. Anthony Fauci did wrong, why he’s in the hot seat now, and when – if ever – modern science & medicine will recover from […]

Chicago Way w/John Kass (07/27/26): Old friend and former boss at WLS-AM, Drew Hayes, joins John Kass and Jeff Carlin to talk about what the differences are between California and Illinois, how media has changed over the years, and what can be done to revive radio. Plus, Kasso wonders how we can rekilter the way […]

Chicago Way w/John Kass (07/20/26): John Kass & Jeff Carlin take a look a the rise of “agenda journalism” in media, what happens when teachers focus on activism instead of education, and why California should be a cautionary take for Illinois. Plus, Kasso wonders if the rise in violent activism is related to Randi Weingarten’s […]

Chicago Way w/John Kass (07/13/26): John Kass & Jeff Carlin welcome retired Chief of Detectives for the Chicago Police Department, Gene Roy, to discuss how dishonorably the outgoing Supt. Larry Snelling was treated by Mayor Brandon Johnson, what it’s like working in an understaffed district, and who should be tabbed to take of the CPD. […]

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 […]

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 […]

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 […]

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 […]

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 […]

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, […]

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. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by using […]

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 […]