The Chicago Way: episodes
60 recent episodes from the show's feed. Back to the show
Chicago Way w/John Kass: On the brink
Jan 26, 2026
Chicago Way w/John Kass (01/26/26): Retired police chief Tom Weitzel (Riverside) joins John Kass & Jeff Carlin to talk about his work with Awake Illinois to stop SB2820 (Introduced by Sen. Laura Fine [D-Glenview]) from being passed. SB2820 would ban anyone who previously worked with Immigration and Customs Enforcement (ICE) from being a law enforcement […]
Chicago Way w/John Kass: Still no compassion from the media or politicians for a father’s loss
Jan 19, 2026
Chicago Way w/John Kass (01/19/26): To mark the tragic anniversary of his daughter’s death, 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-run crash, allegedly caused by a Guatemalan national who was in the country illegally and […]
Chicago Way w/John Kass: The good, the bad, and the ugly of the Illinois’ judiciary
Jan 12, 2026
Chicago Way w/John Kass (01/12/26): Thom Serafin, long-time political strategist, Communicator in Chief of Serafin & Associates, & newly collaborating with Mercury Illinois, joins John Kass & Jeff Carlin with some much needed perspective on who are the Cook County Bar Association & the Chicago Council of Lawyers, and why are they upset over a […]
Chicago Way w/John Kass: Charles Lipson looks at how 2026 might unfold
Jan 5, 2026
Chicago Way w/John Kass (01/05/26): This week, Charles Lipson joins John Kass & Jeff Carlin to start off the new year. 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. On […]
Chicago Way w/John Kass: Like frogs in a pot, happy New Year
Dec 30, 2025
Chicago Way w/John Kass (12/30/25): Happy New Year from the Chicago Way. John Kass & Jeff Carlin look at the end of the year and who might be eligible for the first-ever Moutza of the Year. Obvious contenders are Chicago Mayor Brandon Johnson, Cook County Board President Toni Preckwinkle, and Illinois Governor JB Pritzker, but […]
Chicago Way w/John Kass: O Holy Night
Dec 24, 2025
Chicago Way w/John Kass (12/24/25): Merry Christmas, Kyrie Elaison. John Kass reads ‘O Holy Night,’ his annual Christmas column. Blessings to all! Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! Follow Everything John Kass
Chicago Way w/John Kass: A Christmas soup debate
Dec 19, 2025
Chicago Way w/John Kass (12/19/25): Greetings, good tidings, and cheer from John Kass & Jeff Carlin at The Chicago Way podcast. In this last collab before the traditional Christmas column reading, John sets the table for a Kass family soup competition. Plus, Kasso shares the story of our dearly departed Zeus the Wonderdog enjoying too […]
Chicago Way w/John Kass: A funeral for a friend and the city’s finances
Dec 15, 2025
Chicago Way w/John Kass (12/15/25): Austin Berg, Executive Director of the Chicago Policy Center at the Illinois Policy Institute, join John Kass & Jeff Carlin with a look at just how badly Mayor Brandon Johnson has managed Chicago’s finances and the inane ideas the Mayor has come up with to fill a nearly $1.2 billion […]
Chicago Way w/John Kass: Why Pastor Brooks has zero confidence in Mayor Johnson
Dec 8, 2025
Chicago Way w/John Kass (12/08/25): Pastor Corey Brooks joins John Kass & Jeff Carlin to discuss how his fundraising effort to walk across the entire United States in a year is going, why he has zero confidence in Chicago Mayor Brandon Johnson, what former mayor Daley said to him, and where he’s been eating along […]
Chicago Way w/John Kass: Retired police chief talks SAFE-T Act reforms, Reed case
Dec 1, 2025
Chicago Way w/John Kass (12/01/25): This week, retired Police Chief, Tom Weitzel (Riverside), joins John Kass & Jeff Carlin to talk about who is to blame for the release of veteran convict Lawrence Reed –who allegedly poured gasoline over 26-year-old Bethany MaGee at random, setting her on fire aboard a Blue Line train– and what […]
Chicago Way w/John Kass: A Thanksgiving need for a warm cup of Midwestern common sense
Nov 24, 2025
Chicago Way w/John Kass (11/24/25): Thanksgiving is upon us, but senseless violence continues to plague the city, and John Kass wonders if the judges who let career violent criminals back on the street to destroy more lives will ever be held accountable? Kasso is thankful for a good cup of Kribi Coffee and supports their […]
Chicago Way w/John Kass: Who can heal the basket case city?
Nov 17, 2025
Chicago Way w/John Kass (11/17/25): Paul Vallas is here to talk about his latest column- “Chicago’s Killing Fields”, Mayor Brandon Johnson’s awful policies, and the time he played the role of Barney. Plus, Kasso remembers his time in the saddle and a good horse. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, o
Chicago Way w/John Kass: A recipe for compromise
Nov 11, 2025
Chicago Way w/John Kass (11/11/25): Chicago Ald. Ray Lopez (15th) is here to explain his amnesty plan to John Kass & Jeff Carlin and discuss why he’s not surprised Chuy Garcia used old-school machine politics to retire on another public pension and coronate his ‘Leftino” successor. Plus, Kasso welcomes Kribi Coffee into the fold. Check […]
Chicago Way w/John Kass: A smile to bring down a city
Nov 3, 2025
Chicago Way w/John Kass (11/03/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin this week to discuss what Zohran Mamdani’s role as a leader of the modern Democratic Party will look like, how the U.S. is going to respond to the […]
Chicago Way w/John Kass: Revolutionary times
Oct 27, 2025
Chicago Way w/John Kass (10/28/25): This week, John Kass & Jeff Carlin wax philosophically about how the U.S. found itself in revolutionary times and where do we go from here. Plus, Kasso wonders if New York is ready for what it’s voting for? Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X […]
Chicago Way w/John Kass: ‘No Kings’ rallies and Pritzker’s gambling habits
Oct 20, 2025
Chicago Way w/John Kass (10/20/25): RealClear Politics’ Tom Bevan is here with a post-op on what impact the “No Kings” rallies (Chicago’s rally featured one of Illinois’ top gamblers -Gov. JB Pritzker (D), for whom Tom has a some choice words) will have, why he thinks this government shutdown will break the 2018-2019 shutdown record […]
Chicago Way w/John Kass: Chaos reigns over local LEO/FED interactions, almost by design
Oct 13, 2025
Chicago Way w/John Kass (10/13/25): This week, Garry McCarthy – former Chicago Police Department (CPD) Superintendent and current Chief of Police for Willow Springs, IL- joins John Kass and Jeff Carlin to discuss a disturbing dispatch call involving CPD, Customs and Border Protection (CBP), Immigration and Customs Enforcement (ICE), Cook County Sheriffs, & Illinois State […]
Chicago Way w/John Kass: An origin story
Oct 6, 2025
Chicago Way w/John Kass (10/06/25): Fall is officially here and so is story time. John Kass tells Jeff Carlin about standing outside Wrigley Field in 1984 and the series of events that lead him there. Plus, Kasso gets an apology. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X (Twitter). Tell your […]
Chicago Way w/John Kass: A retired judge on how a bad apple can spoil the bunch
Sep 29, 2025
Chicago Way w/John Kass (09/29/25): This week, the Honorable Judge James R. Brown (ret.) joins John Kass & Jeff Carlin to talk about the moment soon-to-be-former Chief Judge Timothy Evans gathered bond court judges to direct them to go against the rule of law and let violent offenders off easy, lest the judges be reassigned. […]
Chicago Way w/John Kass: What the FCC’s Carr got wrong about Jimmy Kimmel
Sep 22, 2025
Chicago Way w/John Kass (09/22/25): Dan Proft, co-host of “The Morning Answer” radio program 5-9 a.m. on WIND AM 560, is this week’s guest joining John Kass & Jeff Carlin with a breakdown of the FCC meddling in the Jimmy Kimmel fiasco and what it will take to push the JB Pritzkers of the world […]