The Chicago Way

Chicago Way w/John Kass (04/06/26): Charles Lipson joins Jeff Carlin (John Kass is out this week) to talk about how war in Iran will alter President Donald Trump’s legacy as Commander-in-Chief Charles. Charles is the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago and an author whose writings can be […]

Chicago Way w/John Kass (03/30/26): This week, John Kass & Jeff are joined by Rafael Mangual, the Nick Ohnell Fellow and head of research for the Policing & Public Safety Initiative at the Manhattan Institute and a contributing editor of City Journal. On the docket, why Democrats make excuses for violent crimes, ignore the pain […]

Chicago Way w/John Kass (03/23/26): Former State Rep. Tom Morrison is here to talk about his ‘complete ​blueprint for winning ​a local or state race’ at CandidateMasterclass.com and why it is so important as the country prepares to mark the 250th anniversary of the signing of the Declaration of Independence, everyone takes an active role […]

Chicago Way w/John Kass (03/17/26): This week, the Honorable Judge James R. Brown (ret.) returns to the podcast with Brendan Philbin, Senior Counsel at the Liberty Justice Center, to discuss a federal civil rights lawsuit filed on behalf of Judge Brown, who was removed from his judicial recall appointment after Illinois Supreme Court justices retaliated […]

Chicago Way w/John Kass (03/10/26): 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 to discuss the Illinois governor’s race, specifically the Republican primary that has seen second-time candidate Darren Bailey take umbrage with Dan being paid to work […]

Chicago Way w/John Kass (03/03/26): John Kass is back. John joins Jeff Carlin to talk about what’s kept him away and what’s next. Plus, Kasso wonders if we really appreciate what we have? Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. […]

Chicago Way w/John Kass (02/23/26): Nicholas Kass steps in for Jeff Carlin & John Kass as illness plagues the Kasso-sphere to present one of his favorite JohnKassNews.com columns, Riding a Good Horse in the Snow, Part 2. Nick is a regular contributor and, most notably, a retired U.S. Foreign Service officer, diplomat, and Intelligence expert […]

Chicago Way w/John Kass (02/16/26): Mike “Houli” Houlihan, a well-known Irish-American actor, filmmaker, stand-up comedian, and former Chicago Sun-Times columnist, joins Jeff Carlin while John Kass regains his voice. Houli has a new piece on JohnKassNews.com and is always working on multiple projects at Hibernian Media. Check out more from Kass at JohnKassNews.com or contact me at [email protected], […]

Chicago Way w/John Kass (02/09/26): Charles Lipson is back playing pinch-hitter for John Kass, who lost his voice educating bright young minds at Hillsdale College, and joins Jeff Carlin with a dive into how we quantify trust. Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. […]

Chicago Way w/John Kass (02/02/26): RealClear Politics’ Tom Bevan is here to discuss how we got ourselves to tenuous climate in American politics, what we can learn from his Princeton senior thesis, and why Don Lemon is going to be okay, even if he tells you different. Plus, Kasso wonders if there is a more […]

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 (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 (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 [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow […]

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 [email protected], or Facebook, or […]

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 [email protected], 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 [email protected], 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 […]