The Chicago Way

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 […]

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 […]

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 […]

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 […]

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? Follow Everything John […]

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. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin […]

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. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by […]

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 […]

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 […]

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 […]

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 […]

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 […]

Chicago Way w/John Kass (08/03/26): This week, Dr. Cory Franklin – who spend over 25 years at Cook County Hospital in Chicago, joins Jeff Carlin to make sense of what Dr. Anthony Fauci did wrong, why he’s in the hot seat now, and when – if ever – modern science & medicine will recover from […]

Chicago Way w/John Kass (07/27/26): Old friend and former boss at WLS-AM, Drew Hayes, joins John Kass and Jeff Carlin to talk about what the differences are between California and Illinois, how media has changed over the years, and what can be done to revive radio. Plus, Kasso wonders how we can rekilter the way […]

Chicago Way w/John Kass (07/20/26): John Kass & Jeff Carlin take a look a the rise of “agenda journalism” in media, what happens when teachers focus on activism instead of education, and why California should be a cautionary take for Illinois. Plus, Kasso wonders if the rise in violent activism is related to Randi Weingarten’s […]

Chicago Way w/John Kass (07/13/26): John Kass & Jeff Carlin welcome retired Chief of Detectives for the Chicago Police Department, Gene Roy, to discuss how dishonorably the outgoing Supt. Larry Snelling was treated by Mayor Brandon Johnson, what it’s like working in an understaffed district, and who should be tabbed to take of the CPD. […]

Chicago Way w/John Kass (07/07/26): Happy Birthday America! Charles Lipson joins John Kass & Jeff Carlin for a look at who is pushing the narrative that the US is bad, why people can’t seem to agree on common sense anymore, and what is at risk if we dismantle institutions like the Constitution. Charles is Professor […]

Chicago Way w/John Kass (06/30/26): John Kass & Jeff Carlin are back this week to dive into what the current state of American culture means to the rest of the world, how failures that stack up when we elect/hire/listen to unqualified leaders, and a stack of questions from listeners. Plus, Kasso is VERY confident the […]

Chicago Way w/John Kass (06/22/26): Re-Issue: Episode #6 from 02/10/206. Cartoonist Scott Stantis joins John Kass & Jeff Carlin to discuss what turns out to be the end of Rahm Emanuel’s tenure as Chicago Mayor, the 2016 primary season featuring Hillary Clinton vs. Bernie Sanders & Donald Trump vs. establishment everything, and meet two drivers […]

Chicago Way w/John Kass (06/15/26): John Kass & Jeff Carlin are together to talk about the things we don’t talk about when violence happens, how Chicago Democrats let the Bears go to Indiana to save face, and why the Obama Presidential Center allegedly owes people money, already. Plus, Kasso remembers the first time meeting his […]

Chicago Way w/John Kass (06/08/26): John is off this week, celebrating his son’s wedding, so we bring you a reissue from January of 2016. The first episode, featuring John Kass, Will Lee, and Jeff Carlin, talking about a strange hat controversy at a local TV station, bizarre news stories on TV, Will’s amazing story about […]

Chicago Way w/John Kass (05/31/26): Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin with questions about Chuy Garcia’s old school political tactics, whether or not Brandon Johnson has the heart to run for re-election, and why his fellow alders are finally getting behind his proposal to hold parents of violent teens accountable? Also, […]

Chicago Way w/John Kass (05/26/26): John Kass & Jeff Carlin celebrate the bravery it takes to face violent warm summer nights in Chicago in the face of gang wars and ‘teen takeovers.’ Plus, Kasso has a ‘Happy’ pet peeve. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by using […]

Chicago Way w/John Kass (05/18/26): John Kass & Jeff Carlin are joined by former (possibly, future?) candidate for Mayor of Chicago, head of the public school systems in Chicago, Philadelphia and the Louisiana Recovery School District, Paul Vallas to talk about recent attacks on him, who he thinks might be behind it, and what he […]

Chicago Way w/John Kass (05/11/26): John Kass & Jeff Carlin remember his late mother, Betty Kass, and as she would have wanted, move on to the ugly Obama Presidential Center building, Chicago alders wanting Walgreens to be criminally charged for closing stores, and Stephen Colbert smirking his way through a farce of an interview with […]

Chicago Way w/John Kass (05/05/26): On this episode, revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin to discuss how tipping became an american tradition and what it means to the industry. Plus, Kasso wonders if there is a trick to surviving Mother’s Day at a restaurant? Follow Everything John Kass – JohnKassNews.com […]

Chicago Way w/John Kass (04/27/26): John Kass & Jeff Carlin tackle news of the week including a Chicago Police officer being killed in the line of duty, chaos at the White House Correspondents’ Dinner, and news former Mayor Richard M. Daley is recovering from a stroke. Plus, Kasso wonders if the Chicago Teachers’ Union take […]

Chicago Way w/John Kass (04/20/26): Nicholas S. Kass joins John Kass & Jeff Carlin to talk about his latest piece, Keep the Kurds Out of the Iran War, in the American Conservative. Nick is John’s younger brother and served in the U.S. government for over 30 years at the White House/National Security Council, State Department, […]

Chicago Way w/John Kass (04/13/26): John Kass is back with Jeff Carlin to catch up on some big news from John’s brother Nick, our friend Sal Carmada, and a budding feud on JohnKassNews.com. Plus, Kasso urges everyone to take of your heart, your spiritual heart. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, […]

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 john@johnkassnews.com, 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 john@johnkassnews.com, […]

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 john@johnkassnews.com, 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 john@johnkassnews.com, 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 […]