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The Chicago Way — News
The Chicago Way

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.

Copyright: © WGN Plus, All Rights Reserved

Latest Episodes:

Chicago Way w/John Kass: How do we rekilter our media intake? Jul 27, 2026

Show notes

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 people absorb information.

https://serve.castfire.com/audio/8542028/8542028_2026-07-27-191328.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
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The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

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Kass: When good food is simple, what more do you need?

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Chicago Way w/John Kass: A hooley of a good time

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Kass: Mayor Brandon Johnson and the 40 flies

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Kass: Chicago Flips Red’s candidate for mayor

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Chicago Way w/John Kass: When education becomes indoctrination Jul 20, 2026

Show notes

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 role at the American Federation of Teachers?

https://serve.castfire.com/audio/8526034/8526034_2026-07-20-150134.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: When cops become decoys Jul 13, 2026

Show notes

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. Plus, Kasso wonders if the next mayor of Chicago will have what it takes to set things right?

https://serve.castfire.com/audio/8507056/8507056_2026-07-13-201856.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: 250 years of common sense, now this? Jul 06, 2026

Show notes

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 Emeritus of Political Science at University of Chicago and you can read him at CharlesLipson.com Plus, Kasso is wonders if anyone noticed Chicago Police Supt. Larry Snelling fleeing the sinking ship that is Mayor Brandon Johnson’s tenure?

https://serve.castfire.com/audio/8493426/8493426_2026-07-06-180126.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: How the world realized America is great Jun 29, 2026

Show notes

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 USMNT will win it all at FIFA World Cup.

https://serve.castfire.com/audio/8482093/8482093_2026-06-29-193233.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016 Jun 22, 2026

Show notes

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 of the famous Oscar Meyer Wienermobile. Plus, Kasso reads his column about courting his lovely bride, Betty.

https://serve.castfire.com/audio/8468587/8468587_2026-06-22-175627.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: What we don’t talk about says a lot Jun 15, 2026

Show notes

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 former legman, Will ‘Old School’ Lee, covering a murder.

https://serve.castfire.com/audio/8453226/8453226_2026-06-15-214826.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: Reissue – Episode #1 from January of 2016 Jun 08, 2026

Show notes

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 life on the South Side of Chicago, and Rahm Emanuel’s never-ending headache. Plus, John tells the story of the first time he was burned by a lying witness.

https://serve.castfire.com/audio/8438342/8438342_2026-06-08-162342.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: Does Mayor Brandon Johnson even want to run again? May 31, 2026

Show notes

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, Ald. Lopez can’t explain why Mayor Brandon Johnson would give Pope Leo a Cubs hat, but Ray knows why he’s running for re-election in the 15th ward. Plus, Kasso wonders if Indiana should change the state slogan to ‘FAFO?’

https://serve.castfire.com/audio/8421703/8421703_2026-05-31-170803.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

Chicago Way w/John Kass: Summer is for the brave May 26, 2026

Show notes

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.

https://serve.castfire.com/audio/8411305/8411305_2026-05-26-215205.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
Follow @John_Kass Follow @JPCarlin
Download this episode here by using ‘Save As’ here
Subscribe to The Chicago Way

Recent Posts

The Chicago Way with John Kass

Chicago Way w/John Kass: The time is now for independent media in Illinois

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: When good food is simple, what more do you need?

.cls-7{fill:#fff;fill-rule:evenodd}

Chicago Way w/John Kass: A hooley of a good time

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Mayor Brandon Johnson and the 40 flies

.cls-7{fill:#fff;fill-rule:evenodd}

Kass: Chicago Flips Red’s candidate for mayor

.cls-7{fill:#fff;fill-rule:evenodd} Click for more

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