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 Texas to the fierce post-election blame game targeting J.D. Vance, Susie Wiles, and Stephen Miller, they dissect how a perfect storm of an unexpected war in Iran, rising gas prices, and systemic swamp corruption alienated moderates and energized the Democratic base. Bevan also shares a heartfelt, touching tribute to Kass’s legendary journalism career, celebrating his decades of writing four columns a week for the Chicago Tribune.

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 Lopez pulls no punches on what it takes to bring common-sense governance back to the city.

Key Topics Covered:

Don’t miss this sharp, candid conversation on the real-world consequences of Chicago policy, safety, and the fight to keep politicians’ hands out of the city’s critical funds.

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 walk down memory lane to tell the true origin story of the show:How an impromptu run-in outside Tribune Tower with the smoker’s circle launched a partnership spanning over a decade and 566 episodes. Also, Kasso offers a heartfelt thank you to everyone who listened, supported, and rode along 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?