The Chicago Way

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 is a board member of NTN and formerly a candidate for Lt. Governor of Illinois alongside Ted Dabrowski.

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 against bias. Plus, Kasso wonders if ‘Augustus Gloop’ will ever give be held to account for what he’s done to Illinois?

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?

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.

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.

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 clique of candidates is ready for an outsider?

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 wonders who else could be considered a skunk at the garden party?

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 around them, and what the 2028 election cycle will look like. Plus, Kasso wonders if voters in the 2026 Chicago mayoral election realize they’re all Augustus Gloop?

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 ‘Jaws’ Giorango is still on good terms with Alexi Giannoulias?

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 Political Science Emeritus at the University of Chicago and an author whose writings can be found in the Spectator, Spectator World, The Telegraph, and more. Plus, Kasso offers an update on his health.