The Chicago Way

Latest Episodes:

Chicago Way w/John Kass: Don’t (bleep) with a pit bull’s reputation May 18, 2026

Show notes

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 aims to do about it. Plus, Kasso wonders if those in the know are ready for when the pit bull jumps the fence?

https://serve.castfire.com/audio/8391532/8391532_2026-05-18-204732.64kmono.mp3
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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: Hopium and the well-dressed chili powder thief May 11, 2026

Show notes

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 former-President Obama. Plus, Kasso tells the story of the well-dressed chili powder thief.

https://serve.castfire.com/audio/8373531/8373531_2026-05-11-215631.64kmono.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

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

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Kass: Chicago Flips Red’s candidate for mayor

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

Chicago Way w/John Kass: ‘Tips’ for Mother’s Day May 04, 2026

Show notes

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?

https://serve.castfire.com/audio/8357043/8357043_2026-05-04-204743.64kmono.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

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: A different time in D.C. Apr 27, 2026

Show notes

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 over of the Chicago Public Schools and City Hall can ever be corrected?

https://serve.castfire.com/audio/8338261/8338261_2026-04-27-201501.64kmono.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

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: On the hunt for politicization in U.S. intelligence Apr 20, 2026

Show notes

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, CIA, and until January of this year, was the acting chairman of the National Intelligence Council in the Office of the Director of National Intelligence (ODNI).

https://serve.castfire.com/audio/8292985/8292985_2026-04-19-213825.64kmono.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

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: A time for reflection Apr 13, 2026

Show notes

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, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today!

https://serve.castfire.com/audio/8228878/8228878_2026-04-13-171718.64kmono.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

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: Trump’s Iranian tightrope Apr 06, 2026

Show notes

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 found in the Spectator, Spectator World, The Telegraph, and more. Check him out at CharlesLipson.com

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!

https://serve.castfire.com/audio/8079157/8079157_2026-04-06-153057.64kmono.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

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: Alders warn us ‘wrong place, wrong time’ but they created this Mar 30, 2026

Show notes

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 of victims, and is the media silent to the cries of parents? Plus, Kasso tires to understand what Chicago Alder. Maria Hadden means when she says a dead Loyola student was in the ‘wrong place and wrong time’ are in Chicago?

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!

https://serve.castfire.com/audio/8066086/8066086_2026-03-30-161926.64kmono.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

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: A blueprint for getting involved in the Republic Mar 23, 2026

Show notes

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 in keep the republic healthy. Tom also talks with John Kass & Jeff Carlin how Hillsdale College prepared him for his career.

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!

https://serve.castfire.com/audio/8053522/8053522_2026-03-23-203622.64kmono.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

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: Authoritarianism cometh from Springfield Mar 17, 2026

Show notes

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 against him for exercising his First Amendment rights as a private citizen. Plus, Kasso wonders if when we’re really faced with authoritarianism, will we recognize it?

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!

https://serve.castfire.com/audio/8040696/8040696_2026-03-17-194536.64kmono.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