Chicago Way w/John Kass (02/16/24): Austin Berg is here from the Illinois Policy Institute with a breakdown of how things are going at the Chicago Teachers Union controlled City Hall. Austin joins John Kass & Jeff Carlin with a look at how Cook County President Toni Preckwinkle is attempting to distance themselves from Mayor Brandon Johnson after a series of missteps around Chicago’s ShotSpotter gunfire detection contract and the importance of voting in Chicago’s March primary election with candidates for Cook County State’s Attorney & a ‘mansion tax’ referendum on the ballot. Plus, Kasso wonders if CTU President Stacey Davis-Gates has sumptuous wood floors in her Indiana home?

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Chicago Way w/John Kass (02/12/24): 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 Kass. The younger Kass breaks down what happens when the ‘deep state’ needs to discard a useful idiot and how state security analysts around the world glean intel from interviews world leaders like Joe Biden & Vladimir Putin give to journalists. Plus, Kasso sheds light on the story of how his father made him take on 10 guys in a street fight.

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Chicago Way w/John Kass (02/05/24): On episode 426, Senior Technical Producer & life-long southside resident of Chicago Brian Althimer joins John Kass & Jeff Carlin to share his perspective as someone who was born Englewood and has seen how crime & disinvestment have changed the South Side of the city over his lifetime. Plus, Kasso wonders what secrets Brian can offer about Jeff Carlin.

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Chicago Way w/John Kass (01/29/24): This week, Amber Duke (Athey) joins John Kass & Jeff Carlin to discuss her new book, ‘The Snowflakes’ Revolt: How Woke Millennials Hijacked American Media.’ Amber also talks about being cancelled at WMAL and how newsrooms across the country have lost their credibility after allowing ‘Snowflakes’ to press their ill-conceived agenda.

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Chicago Way w/John Kass (01/22/24): RealClear Politics’ Tom Bevan breaks down what Florida Governor Ron DeSantis’s campaign got foolishly wrong, how the GOP ’24 primary is really a Vice Presidential primary, why Nikki Hailey will never be Donald Trump’s VP pick (but Elise Stefanik or Tim Scott will be), and what happens when liberals realize Joe Biden isn’t going to cut it? (Will Tom’s Michelle Obama prediction finally come true?) Plus, Kasso needs a wine that goes well with fly fishing.

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Chicago Way w/John Kass (01/15/24): This week, hometown reporter Anita Padilla talks about her time covering Chicago and what is next as she embarks on a new role as News Director for Florida’s Voice. Plus, John Kass & Jeff Carlin wonder if Mayor Brandon Johnson is cracking from the pressure of membership in Chicago’s clown-carpool of politics?

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Chicago Way w/John Kass (01/01/24): To close out 2023, friend of the show Charles Lipson (the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago) joins John Kass & Jeff Carlin to discuss Charles’ piece in RealClearPolitics about Chicago Mayor Brandon Johnson’s ‘Hat Trick of Dreadful Policies’ and what that means for 2024. Plus, Kasso wonders how the migrant influx impact the DNC convention this summer?

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Chicago Way w/John Kass (12/25/23): John Kass & Jeff Carlin discuss former Chicago Way power broker Ed Burke being found guilty of corruption after serving more than 45 years on the City Council and what that means for the verdict in the future of the Chicago Way. Plus, Kasso wonders who has earned the Moutza of the Month for December (Colorado Supreme Court?) and wishes everyone a Merry Christmas & healthy New Year.

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Chicago Way w/John Kass (12/18/23): On this edition, the host of the Counterculture podcast and conservative political advocate Dan Proft joins John Kass & Jeff Carlin to discuss Dan’s first crack at writing a column for John. Kasso also wonders if Dan is up for tackling the ‘Sentimental Barbarian’ and coming around to loving soccer.

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Chicago Way w/John Kass (12/11/23): Joining John Kass & Jeff Carlin this week is John’s younger brother Nicholas Kass, a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on matters pertaining to the Eastern Mediterranean, to discuss why thoughtful foreign policy leadership is so important and how to spot the pretenders. Plus, what happens when reality comes knocking for the Ivy League?

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