The Chicago Way

Latest Episodes:

Chicago Way w/John Kass: The iron triangle of deception Aug 18, 2025

Show notes

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 by deep state actors, the media, & politicians. Plus, Kasso wonders if disgraced FBI Director & sycophantic Swiftie James Comey know how cringy he is?

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/7653671/7653671_2025-08-18-212411.64kmono.mp3
Follow Everything John Kass – JohnKassNews.com
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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: Obama, Pritzker, and the stories they tell Aug 11, 2025

Show notes

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 really just dreams. Plus, Kasso wonders if elected officials in Cincinnati deserve the Moutza of the Month for telling assault victims they were racists & deserved to be attacked.

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/7641734/7641734_2025-08-11-173234.64kmono.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?

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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: Ald. Reilly leading the way for ‘closet moderates’ against Preckwinkle Aug 04, 2025

Show notes

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, Kasso wonders if ex-Chicago Mayor Lori Lightfoot ever saw the far-left coming to devour her political 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/7557885/7557885_2025-08-04-191125.64kmono.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: Dead people voting, flooded basements, and The Nice Man Jul 28, 2025

Show notes

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 to be a minefield of missing information. Plus, Kass wonders why anyone would be against letting dead people vote?

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/7546247/7546247_2025-07-28-171647.64kmono.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 wake-up call for NYC from the Windy City Jul 21, 2025

Show notes

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 Indiana’s favorite relator, Gov. Pritzker.

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/7533359/7533359_2025-07-21-211159.64kmono.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: Freedom rings Jul 07, 2025

Show notes

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, what the ’12 Day War’ between Iran & Israel means for geopolitical relations throughout the Middle East and beyond, how birthright citizenship impacts the U.S. census -and in turn the power balance between traditionally red & blue state, and why the ‘Big Beautiful Bill’ will have a legacy beyond that of Ronald Reagan. Plus, Kasso wonders if the Declaration of Independence is the greatest document ever produced in America?

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! And read writings from John’s brother Nick for the American Conservative here and here.

https://serve.castfire.com/audio/7508291/7508291_2025-07-07-184231.64kmono.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 road at the Sicilian Summer Block Party Jun 30, 2025

Show notes

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 the tale of the podcast’s origin story.

https://serve.castfire.com/audio/7498597/7498597_2025-06-30-163437.64kmono.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: Business as usual means someone else’s hand in you pocket Jun 23, 2025

Show notes

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 usual will ever change?

https://serve.castfire.com/audio/7486398/7486398_2025-06-23-202338.64kmono.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: Straight from the butcher’s mouth Jun 16, 2025

Show notes

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 city’s vibrant food scene. Plus, Kasso has a tip about a special meet & greet event coming up at the first annual Sicilian Summer Block Party on the city’s northwest side.

https://serve.castfire.com/audio/7472840/7472840_2025-06-15-202040.64kmono.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: The 80/20 problem Jun 09, 2025

Show notes

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 has come to a fork in the road that will decide the fate of generations to come. Plus, Kasso wonders why SEIU leaders are at the forefront the chaos happening on the streets of Los Angeles.