The Chicago Way

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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 (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 […]

Chicago Way w/John Kass (09/15/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin to talk about the cold-blooded murder of Charlie Kirk and how free speech in the UK is under threat. Plus, Kasso wonders if the Democrat culture of assassination […]

Chicago Way w/John Kass (09/08/25): Newly minted candidate for Illinois Governor Ted Dabrowski of Wirepoints joins John Kass & Jeff Carlin to lay out his plan for convincing the center left & independent voters of the state to help him beat Gov. JB Pritzker in next year’s election. Plus, Kasso wonders if this is the […]

Chicago Way w/John Kass (09/01/25): This week, former Cook County and federal prosecutor Bob Milan joins John Kass & Jeff Carlin to talk about his original plan from 10 years ago to bring in National Guard troops to tamp down the weekly number of shootings in Chicago and how this strategy might work today. Plus, […]

Chicago Way w/John Kass (08/25/25): 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 is suspected of driving under the influence, Julio Cucul […]

Chicago Way w/John Kass (08/18/25): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin with a look at how President Barack Obama’s misdeeds compare to Richard Nixon, what candidate for mayor Zohran Mamdani means for NYC, and whether voters will ever get out from the stranglehold of the Iron Triangle deception created […]

Chicago Way w/John Kass (08/11/25): This week, John Kass & Jeff Carlin tackle JB Pritzker’s hypocrisy when it comes gerrymandering, evidence that President Barack Obama was trying to convince people Russia got Trump elected in 2016 -even though we know they didn’t, and look at why dreams of living on the Moon or Mars are […]

Chicago Way w/John Kass (08/04/25): Chicago Alderman Brendan Reilly (42nd) joins John Kass & Jeff Carlin to announce that his circulating petitions and seriously considering running against Cook County Board President Toni Preckwinkle. Ald. Reilly talks about wanting to course correct years of democratic socialist policies that have left the county broke & bloated. Plus, […]