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Mild mannered Chicago Tribune columnist John Kass and WGN Radio's Jeff Carlin explore the week in news, politics and other thngs done the Chicago Way in this WGN Plus podcast from WGN Radio in Chicago.
530 Episodes
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1Chicago 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, […]
Chicago Way w/John Kass (07/28/25): This week, Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin to discuss how Mayor Brandon Johnson has let flooding plague the city, year after year, while he spends time picking fights with President Donald Trump. Ray also wonders if intellectual curiosity is dead and why Chicago’s voter rolls seem […]
Chicago Way w/John Kass (07/21/25): On this episode, Ted Dabrowski of Wirepoints.com joins John Kass & Jeff Carlin to highlight how Governor JB Pritzker is delusional about Illinois’ status as an ‘economic powerhouse’ and to warn the voters of New York City about the perils of electing unserious socialists. Plus, Kasso offers a hat-tip to […]
Chicago Way w/John Kass (07/07/25): Charles Lipson joins John Kass & Jeff Carlin for this post Independence Day episode. 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 the docket, […]
Chicago Way w/John Kass (06/30/25): On a HOT summer Sunday, John Kass & Jeff Carlin head out to the first annual Sicilian Summer Block Party in the Dunning neighborhood to break bread and enjoy some entertainment. Along the way, fans of John’s share stories about what the Chicago Way means to them. Plus, Kasso tells […]
Chicago Way w/John Kass (06/23/25): On this episode, revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin with a look at the history of the ‘Chicago Way’ -alderman, committee men, cops, etc. shaking down small biz- and how it personally has impacted his family through the generations. Plus, Kasso wonders if business as […]
Chicago Way w/John Kass (06/16/25): This week, John Kass & Jeff Carlin are pleased to welcome Sal Camarda from Joseph’s Finest Meats to talk about his family’s tradition of bringing the best quality meats, sausages, and more to Chicago. Sal, along with his brother Ben, are second generation proprietors and enjoy being part of the […]
Chicago Way w/John Kass (06/09/25): Prof. Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago (whose writings can be found in the Spectator, Spectator World, The Telegraph, and more), is here to explain why Democrats keep ending up on the wrong side of ’80/20 problems’ and how American culture […]
Chicago Way w/John Kass (06/02/25): This week, John Kass & Jeff Carlin discuss the merits of President Donald Trump commutating the federal sentence of notorious gang kingpin Larry Hoover and feds seeking to put former Illinois Speaker of the House Mike Madigan in jail for 12 years at the age of 83. Plus, Kasso urges everyone […]
Chicago Way w/John Kass (05/27/25): This week, John Kass tries to get to the bottom of Jeff Carlin’s bad mood by sharing stories from his weekend in the city celebrating his wedding 39th wedding anniversary. Plus, Kasso wonders if his love for Chicago can ever be redeemed. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, […]
Chicago Way w/John Kass (05/19/25): RealClear Politics’ Tom Bevan is here to discuss James Comey selling seashells by the seashore and what could be considered one of the greatest scandals in presidential history, the cover-up of Joe Biden’s health problems. John Kass & Jeff Carlin also ask Tom about Rahm Emanuel facing off against JB Pritzker in […]
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Congratulations to @JPCarlin on getting married.
The long serving politicians got us here and voters have no one to blame but themselves. In Chicago and Cook County we need a two party system. Not just the Democrat Party. People need to get more involved with politics and not just sports. Chicago can do better! Thanks Chicago Way for informing everyone!!
Good episode on Pro Publica articles.
Ah, The 29 Halcyon Days! Need to shower after listening. Good work, John.