The Chicago Way

Jan 27 2025 100 ep. 747

The Chicago Way Podcast artwork

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.

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Chicago Way w/John Kass: The Good, the Bad, & the Incompetent

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 […]

Chicago Way w/John Kass: Trump 2.0

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 […]

Chicago Way w/John Kass: Idiot Wind

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 […]

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

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 […]

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

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 […]

Merry Christmas, from the Chicago Way

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 […]

Chicago Way w/John Kass: Mayor ‘Brandito’ scrambles, Alders coalesce, and budget flounders

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. Plu

Chicago Way w/John Kass: Can Trump’s DOGE-machine permanently remake govt?

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, […]

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

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 […]

Chicago Way w/John Kass: Thankful for freedom and a good brine recipe

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, […]