PODCAST

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.

news & politics

All Episodes

Chicago Way w/John Kass: Idiot Wind

The Chicago Way ·

2025/01/13

Chicago Way w/John Kass (01/13/25): On this episode, Austin Berg is here from the Illinois Policy Institute to explain why Chicago needs a charter, a new mayor, and better fiscal sense to John Kass & Jeff Carlin. Plus, Kasso wonders if Idiot Wind(s) is a only a coastal concern? Check out more from Kass at JohnKassNews.com or […]

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Chicago Way w/John Kass: Hot Toddy or Buttered Rum?

The Chicago Way ·

2025/01/06

Chicago Way w/John Kass (01/06/25): In the first episode of 2025, John Kass & Jeff Carlin try to make sense of this year’s collection of the Presidential Medal of Freedom recipients, look forward to what 2025 has in store, and share a couple of recipes for staying warm. Plus, Kasso offers up a couple of […]

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Chicago Way w/John Kass: A chance to get things right...

The Chicago Way ·

2024/12/30

Chicago Way w/John Kass (12/30/24): Joining John Kass & Jeff Carlin on the last episode of 2024 is a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on Middle East security matters and who also happens to be John’s younger brother, Nicholas S. Kass. The discussion centers […]

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Merry Christmas, from the Chicago Way

The Chicago Way ·

2024/12/23

Chicago Way w/John Kass (12/23/24): On the Christmas Edition, John Kass & Jeff Carlin are joined by Jude Russo, the managing editor of The American Conservative, with a look at how the President-elect Donald Trump’s challenges in 2025 and what it means be a conservative in the modern Republican party. Plus, Kass has a Christmas […]

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Chicago Way w/John Kass: Mayor ‘Brandito’ scrambles,...

The Chicago Way ·

2024/12/16

Chicago Way w/John Kass (12/16/24): On this edition, Ald. Ray Lopez (15th) discusses what it takes for Chicago Mayor Brandon “Brandito” Johnson to have his approval rating drop to 14% and whether or not Lopez & the coalition of Alders opposing Johnson’s rubberstamp agenda can protect the citizens from another ‘parking-meter-esque’ budget deal. Plus, Kasso wonders […]

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Chicago Way w/John Kass: Can Trump’s DOGE-machine...

The Chicago Way ·

2024/12/09

Chicago Way w/John Kass (12/09/24): This week, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson, joins John Kass and Jeff Carlin to talk about his latest piece writings, President-elect Donald Trump’s transition to power, and what Republicans must do now that they have all the cards. Plus, […]

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Chicago Way w/John Kass: When the leftovers are gone

The Chicago Way ·

2024/12/02

Chicago Way w/John Kass (12/02/24): In a post Thanksgiving hangover, John Kass & Jeff Carlin look at what’s next for the mainstream media and ruling class in Washington, Illinois, & Chicago after Donald Trump takes office. Plus, Kasso gets a couple of book suggestions: The Iron Heel & The Elite. Check out more from Kass […]

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Chicago Way w/John Kass: Thankful for freedom and a...

The Chicago Way ·

2024/11/25

Chicago Way w/John Kass (11/25/24): Joining John Kass & Jeff Carlin this week is a veteran, mother, politician, and conservative radio voice in Illinois, Jeanne Ives to talks about the need for Republicans in Illinois to stand up to Gov. JB Pritzker, what Donald Trump’s second term as President will mean for corruption in Illinois, […]

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Chicago Way w/John Kass: Cabinet chaos

The Chicago Way ·

2024/11/18

Chicago Way w/John Kass (11/18/24): As Donald Trump loads up his cabinet with his most loyal supporters, the man behind Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins Jeff Carlin and John Kass with a look at how voting demographics shifted in 2024 and what that means for Trump’s early days […]

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Chicago Way w/John Kass: Taming the Deep State Tiger...

The Chicago Way ·

2024/11/11

Chicago Way w/John Kass (11/11/24): Joining John Kass & Jeff Carlin this week is a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on security matters and who also happens to be John’s younger brother, Nicholas S. Kass. On the docket, Nick lays out what’s next for […]

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Chicago Way w/John Kass: Election anxiety and the...

The Chicago Way ·

2024/11/04

Chicago Way w/John Kass (11/04/24): As the 2024 election cycle winds down, RealClear Politics’ Tom Bevan is here with an analysis of polls, pandering, & punditry. Tom join John Kass & Jeff Carlin with a look at what happens when polls don’t match results and a preview of RealClearPolitic‘s election night live coverage feat. Carl […]

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The Chicago Way: Welcome to the ‘Kass Political...

The Chicago Way ·

2024/10/29

Chicago Way w/John Kass (10/28/24): As Donald Trump rallies his base at Madison Square Garden & Kamala Harris sends Hillary Clinton on the attack, John Kass & Jeff Carlin what happens to the Democrats if things don’t go their way. Plus, Kasso wonders if the ‘F-word’ should be thrown around by those who know nothing […]

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Chicago Way w/John Kass: Countdown to Election Day,...

The Chicago Way ·

2024/10/21

Chicago Way w/John Kass (10/21/24): Two weeks before Election Day, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson, joins John Kass and Jeff Carlin to look at some of his recent pieces on Kamala Harris’ propensity to hurt her own chances, ‘What if the Electoral College vote is […]

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Chicago Way w/John Kass: Brandon Johnson, dirty...

The Chicago Way ·

2024/10/14

Chicago Way w/John Kass (10/13/24): Southwest Side Ald. Ray Lopez (15th) brings John Kass & Jeff Carlin up to speed on Mayor Brandon Johnson clashing with the Chicago City Council, reporters, and decorators as the city faces one financial crisis, after the next. Plus, Kasso wonders who will rise to take on Mayor Johnson in […]

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Chicago Way w/John Kass: Brandon Johnson is a...

The Chicago Way ·

2024/10/07

Chicago Way w/John Kass (10/07/24): On this episode, Ted Dabrowski of Wirepoints.org joins John Kass & Jeff Carlin to talk about how Chicago’s school system fails its students and is driving the city off a financial cliff as Mayor Brandon Johnson pushes CPS CEO Pedro Martinez out. Plus, Kasso wonders what monster will replace the […]

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Chicago Way w/John Kass: Miranda Devine, ‘The Big...

The Chicago Way ·

2024/09/30

Chicago Way w/John Kass (09/30/24): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin to discuss her new book, The Big Guy: How a President and His Son Sold Out America about how the Biden Family has used their influence to manipulate the levers of power and enrich themselves. Plus, Kasso wonders […]

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Chicago Way w/John Kass: Lessons in avoiding a Deep...

The Chicago Way ·

2024/09/23

Chicago Way w/John Kass (09/23/24): Joining John Kass & Jeff Carlin this week is a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on security matters and who also happens to be John’s younger brother, Nicholas S. Kass. On the docket, Iranian-sponsored hacking of the Trump campaign, […]

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Chicago Way w/John Kass: Are Democrats playing ‘Black...

The Chicago Way ·

2024/09/16

Chicago Way w/John Kass (09/16/24): This week, Corey Brooks, the Founder and Senior Pastor at New Beginnings Church & the Founder/CEO of Project H.O.O.D, joins John Kass & Jeff Carlin to talk about why he thinks Democrats continue to ‘play Black people for fools‘ by convincing them to vote against leaders & legislation the would […]

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Chicago Way w/John Kass: Incompetency with a ‘K’

The Chicago Way ·

2024/09/09

Chicago Way w/John Kass (09/09/24): Just ahead of the first head-to-head debate between Vice President Kamala Harris and ex-President Donald Trump, the President of the Independent Women’s Forum, Carrie Lukas, joins John Kass & Jeff Carlin to discuss her piece in The Federalist titled “Kamala Harris’ Campaign Is Making Women Look Incompetent.” Plus, Kasso wonders […]

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Chicago Way w/John Kass: BLTs, MVPs, and the road to...

The Chicago Way ·

2024/09/03

Chicago Way w/John Kass (09/03/24): This week, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins John Kass & Jeff Carlin with insight from his Power Poll Podcast on who the MVP of Chicago’s role as host of the 2024 DNC, why Vice President Kamala Harris’ best plan […]

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