The Chicago Way

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.

Episodes

April 20, 2025
Chicago Way w/John Kass (04/20/25): John Kass takes time to talk about the meaning of Easter (it’s not really about chocolate bunnies and jelly beans) and what it means to his family. From John Kass & Jeff Carlin, Happy Easter, blessings of love. Christos Anesti! Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, […]
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Chicago Way w/John Kass (04/14/25): This week, Charles Lipson is back to talk about how education has changed and how it is impacting institutions of higher learning. Charles is the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago and he joins John Kass and Jeff Carlin for a lively discussion. […]
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Chicago Way w/John Kass (04/07/25): This week, John Kass & Jeff Carlin tackle the often violent ‘street takeovers’ plaguing Chicago’s business district, President Donald Trump’s policy of raising tariffs to put an end to ‘globalization,’ and various district court judges blocking executive actions by President Trump. Plus, Kasso wonders why Chicago’s city leaders are afraid […]
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Chicago Way w/John Kass (03/31/25): On this episode, author and retired director of medical intensive care at Cook County Hospital in Chicago for over 20 years, Dr. Cory Franklin joins John Kass & Jeff Carlin to discuss why the JFK assassination has captivated conspiracy theorists and the general public for decades and what we, if […]
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Chicago Way w/John Kass (03/24/25): John Kass & Jeff Carlin tackle Chicago Mayor Brandon calling himself the second coming of Harold Washington, his campaign donations from a law firm involved in a lawsuit with the city, and how begging for a 3% kickback from city vendors is working out. Plus, Carlin has an early nominee […]
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Chicago Way w/John Kass (03/17/25): A newcomer to the podcast, Chicago Police Chief of Detectives (ret.) Gene Roy joins John Kass & Jeff Carlin to talk about how wearing a badge in Chicago has changed over the last forty years and look at what he sees as major flaws with the criminal justice & courts […]
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Chicago Way w/John Kass (03/10/25): Charles Lipson, joins John Kass & Jeff Carlin this week. 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, President Trump’s address to […]
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Chicago Way w/John Kass (03/03/25): Nicholas S. Kass joins John Kass & Jeff Carlin on the last episode to discuss the momentous blowup between President Donald Trump & President Volodymyr Zelenskyy at the White House and what this means for the future of Europe and NATO. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, […]
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Chicago Way w/John Kass (02/24/25): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin to discuss President Trump’s breakneck first month back in office and why bulldogs like Kash Patel & Elon Musk have the Deep State reeling from the breadth and scope of their efficiency. Plus, Kass wonders if an English Bulldog should be […]
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Chicago Way w/John Kass (02/17/25): This week, John Kass & Jeff Carlin take on the week’s news, starting with the long-awaited guilty verdict in People v. Michael J. Madigan and ending with tear-jerking film recommendations. Also on the docket, ex-governor Rod Blagojevich was back in the headlines after receiving a full pardon from President Donald […]
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Chicago Way w/John Kass (02/10/25): Just in time for Valentine’s Day, Ald. Ray Lopez (15th) explains the special purpose room that houses a bounty of gifts on the 5th Floor of Chicago City Call and why he thinks it will take someone special to help Chicago course-correct before it’s too late. Plus, Kasso wonders who […]
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Chicago Way w/John Kass (02/03/25): This week, 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, joins John Kass & Jeff Carlin to talk about why he signed his name to […]
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Chicago Way w/John Kass (01/27/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin this week with a focus on President Donald Trump’s ‘First Hundred Hours,’ his trips to North Carolina & California, and what pushback from within the GOP he might […]
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Chicago Way w/John Kass (01/20/25): Inauguration Day is here and so is Dan Proft, co-host of “The Morning Answer” radio program and host of ‘Counter Culture’ podcast, to join John Kass & Jeff Carlin with a look at what Lawfare ‘retribution’ and ‘vengeance’ the Trump Administration will dole out with the likes of Kash Patel […]
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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 (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 (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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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 (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 (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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