The Chicago Way

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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.

WGN Plus


    • May 12, 2025 LATEST EPISODE
    • weekly NEW EPISODES
    • 54m AVG DURATION
    • 321 EPISODES

    4.7 from 1,101 ratings Listeners of The Chicago Way that love the show mention: chicago politics, tribune, uncle tom, illinois politics, kasso, reading john, chicagoan, taxpayers, way podcast, milt, chicago area, john and team, machinations, frequent guests, john tells, national politics, columnists, great work john, john s podcast, rosenberg.


    Ivy Insights

    The Chicago Way podcast is an exceptional show that provides listeners with great insights into politics, current events, and local issues. Hosted by John Kass and Jeff Carlin, this podcast never fails to deliver engaging conversations and a touch of humor. Whether you lean left or right politically, the podcast offers an amazing perspective on political issues, with a specific focus on Chicago, Cook County, and Springfield. It is a must-listen if you have an interest in these topics. As someone who leans left of center myself, I truly appreciate the objectivity and fair-mindedness displayed by the podcast.

    One of the best aspects of The Chicago Way podcast is its ability to provide wonderful insights into various topics. Through conversations with guests such as Ald. Ray Lopez and documentarian Caylan Ford, listeners gain a deeper understanding of political issues and human rights abuses. The podcast also features interviews with experts like Dr. Charles Lipson, who offer valuable perspectives on national politics. Moreover, John and Jeff's portrayal of Chicago as it is cuts through any romanticized notions of the city, providing a realistic view of its workings.

    While The Chicago Way podcast excels in many ways, there may be some minor drawbacks for certain listeners. For example, technical difficulties occasionally hinder the listening experience, particularly older episodes showing up in place of new content. However, this does not detract significantly from the overall quality of the show.

    In conclusion, The Chicago Way podcast is a tremendous platform that informs and entertains its audience while offering valuable insights into local and national politics. John Kass and Jeff Carlin do an excellent job in providing objective discussions that appeal to individuals from diverse political backgrounds. From its enlightening conversations to its humor-filled episodes, this podcast is truly brilliant. Whether you are a lifelong resident or someone interested in gaining a deeper understanding of Chicago's political landscape, The Chicago Way is definitely worth checking out.



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    Latest episodes from The Chicago Way

    Chicago Way w/John Kass: Alder pulls back the curtain on Mayor Johnson's patronage scheme

    Play Episode Listen Later May 12, 2025


    Chicago Way w/John Kass (05/12/25): This week, Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin to look at why he thinks Chicago Mayor Brandon Johnson perpetuating a patronage scheme by steering ‘PlayStreets’ contracts away from Latino wards and into wards where Mayor Johnson is trying to curry favor. Also, Ald. Lopez also hints […]

    Chicago Way w/John Kass: When the oligarchs run the show, the people lose

    Play Episode Listen Later May 5, 2025


    Chicago Way w/John Kass (05/05/25): This week, former CEO of the Chicago Public Schools (1995-2001) & candidate for mayor, Paul Vallas joins John Kass & Jeff Carlin with a look at how Governor JB ‘Master Oligarch of Illinois’ Pritzker is doing running the state and shares a stories about being brought before the him to […]

    Chicago Way w/John Kass: Sounds like JB Pritzker is ready for a donnybrook

    Play Episode Listen Later Apr 29, 2025


    Chicago Way w/John Kass (04/29/25): On this edition, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins John Kass & Jeff Carlin with an analysis of how Sen. Dick Durbin announcing he won’t run for reelection will shuffle the deck in Illinois politics and what Illinois Governor JB Pritzker’s […]

    Chicago Way w/John Kass: A time for family

    Play Episode Listen Later Apr 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, […]

    Chicago Way w/John Kass: Where did we go wrong on education?

    Play Episode Listen Later Apr 14, 2025


    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. […]

    Chicago Way w/John Kass: Street takeovers, tariffs, and judges on the loose

    Play Episode Listen Later Apr 7, 2025


    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 […]

    Chicago Way w/John Kass: Anatomy of conspiracy with Dr. Cory Franklin

    Play Episode Listen Later Mar 31, 2025


    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 […]

    Chicago Way w/John Kass: Mayor Brandon ‘Harold Washington' Johnson

    Play Episode Listen Later Mar 24, 2025


    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 […]

    Chicago Way w/John Kass: Why safety on the streets starts in the courtroom

    Play Episode Listen Later Mar 17, 2025


    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 […]

    Chicago Way w/John Kass: Charles Lipson on the truth about ‘free speech' on campus

    Play Episode Listen Later Mar 10, 2025


    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 […]

    Chicago Way w/John Kass: When fools rush in…and out

    Play Episode Listen Later Mar 3, 2025


    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, […]

    Chicago Way w/John Kass: Miranda ‘Bulldog' Devine on Trump's second first month

    Play Episode Listen Later Feb 24, 2025


    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 […]

    Chicago Way w/John Kass: The fall of Madigan and revival of Blago?

    Play Episode Listen Later Feb 17, 2025


    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 […]

    Chicago Way w/John Kass: The messianic complex plaguing the city's future

    Play Episode Listen Later Feb 10, 2025


    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 […]

    Chicago Way w/John Kass: The Tulsi Effect

    Play Episode Listen Later Feb 3, 2025


    Chicago Way w/John Kass (02/03/24): 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 […]

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

    Play Episode Listen Later Jan 27, 2025


    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

    Play Episode Listen Later Jan 20, 2025


    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

    Play Episode Listen Later Jan 13, 2025


    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?

    Play Episode Listen Later Jan 6, 2025


    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

    Play Episode Listen Later Dec 30, 2024


    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

    Play Episode Listen Later Dec 23, 2024


    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 the budget flounders

    Play Episode Listen Later Dec 16, 2024


    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 […]

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

    Play Episode Listen Later Dec 9, 2024


    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

    Play Episode Listen Later Dec 2, 2024


    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

    Play Episode Listen Later Nov 25, 2024


    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, […]

    Chicago Way w/John Kass: Cabinet chaos

    Play Episode Listen Later Nov 18, 2024


    Chicago Way w/John Kass (11/18/24): As Donald Trump loads up his cabinet with his most loyal supporters, the man behind Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins Jeff Carlin and John Kass with a look at how voting demographics shifted in 2024 and what that means for Trump’s early days […]

    Chicago Way w/John Kass: Taming the Deep State Tiger has just begun

    Play Episode Listen Later Nov 11, 2024


    Chicago Way w/John Kass (11/11/24): 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 S. Kass. On the docket, Nick lays out what’s next for […]

    Chicago Way w/John Kass: Election anxiety and the grain rats of the Atlantic

    Play Episode Listen Later Nov 4, 2024


    Chicago Way w/John Kass (11/04/24): As the 2024 election cycle winds down, RealClear Politics' Tom Bevan is here with an analysis of polls, pandering, & punditry. Tom join John Kass & Jeff Carlin with a look at what happens when polls don’t match results and a preview of RealClearPolitic‘s election night live coverage feat. Carl […]

    The Chicago Way: Welcome to the ‘Kass Political Universe' (KPU)

    Play Episode Listen Later Oct 29, 2024


    Chicago Way w/John Kass (10/28/24): As Donald Trump rallies his base at Madison Square Garden & Kamala Harris sends Hillary Clinton on the attack, John Kass & Jeff Carlin what happens to the Democrats if things don’t go their way. Plus, Kasso wonders if the ‘F-word’ should be thrown around by those who know nothing […]

    Chicago Way w/John Kass: Countdown to Election Day, what happens if…

    Play Episode Listen Later Oct 21, 2024


    Chicago Way w/John Kass (10/21/24): Two weeks before Election Day, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson, joins John Kass and Jeff Carlin to look at some of his recent pieces on Kamala Harris’ propensity to hurt her own chances, ‘What if the Electoral College vote is […]

    Chicago Way w/John Kass: Brandon Johnson, dirty laundry, and a SW Side police station

    Play Episode Listen Later Oct 14, 2024


    Chicago Way w/John Kass (10/13/24): Southwest Side Ald. Ray Lopez (15th) brings John Kass & Jeff Carlin up to speed on Mayor Brandon Johnson clashing with the Chicago City Council, reporters, and decorators as the city faces one financial crisis, after the next. Plus, Kasso wonders who will rise to take on Mayor Johnson in […]

    Chicago Way w/John Kass: Brandon Johnson is a disaster for CPS students

    Play Episode Listen Later Oct 7, 2024


    Chicago Way w/John Kass (10/07/24): On this episode, Ted Dabrowski of Wirepoints.org joins John Kass & Jeff Carlin to talk about how Chicago’s school system fails its students and is driving the city off a financial cliff as Mayor Brandon Johnson pushes CPS CEO Pedro Martinez out. Plus, Kasso wonders what monster will replace the […]

    Chicago Way w/John Kass: Miranda Devine, ‘The Big Guy,' and Kamala's future

    Play Episode Listen Later Sep 30, 2024


    Chicago Way w/John Kass (09/30/24): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin to discuss her new book, The Big Guy: How a President and His Son Sold Out America about how the Biden Family has used their influence to manipulate the levers of power and enrich themselves. Plus, Kasso wonders […]

    Chicago Way w/John Kass: Lessons in avoiding a Deep State takeover

    Play Episode Listen Later Sep 23, 2024


    Chicago Way w/John Kass (09/23/24): 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 S. Kass. On the docket, Iranian-sponsored hacking of the Trump campaign, […]

    Chicago Way w/John Kass: Are Democrats playing ‘Black people for fools?' Pastor Corey Brooks says, yes

    Play Episode Listen Later Sep 16, 2024


    Chicago Way w/John Kass (09/16/24): This week, Corey Brooks, the Founder and Senior Pastor at New Beginnings Church & the Founder/CEO of Project H.O.O.D, joins John Kass & Jeff Carlin to talk about why he thinks Democrats continue to ‘play Black people for fools‘ by convincing them to vote against leaders & legislation the would […]

    Chicago Way w/John Kass: Incompetency with a ‘K'

    Play Episode Listen Later Sep 9, 2024


    Chicago Way w/John Kass (09/09/24): Just ahead of the first head-to-head debate between Vice President Kamala Harris and ex-President Donald Trump, the President of the Independent Women’s Forum, Carrie Lukas, joins John Kass & Jeff Carlin to discuss her piece in The Federalist titled “Kamala Harris' Campaign Is Making Women Look Incompetent.” Plus, Kasso wonders […]

    Chicago Way w/John Kass: BLTs, MVPs, and the road to the White House

    Play Episode Listen Later Sep 3, 2024


    Chicago Way w/John Kass (09/03/24): This week, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins John Kass & Jeff Carlin with insight from his Power Poll Podcast on who the MVP of Chicago’s role as host of the 2024 DNC, why Vice President Kamala Harris’ best plan […]

    Chicago Way w/John Kass: Kamala Harris, the perfect Rorschach candidate

    Play Episode Listen Later Aug 26, 2024


    Chicago Way w/John Kass (08/26/24): 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 assess the DNC in Chicago, look at what RFK Jr. brings to Donald Trump’s campaign, and gauge what Democrats see in Vice President Kamala Harris […]

    Chicago Way w/John Kass: DNC 2024 is here, are you ready?

    Play Episode Listen Later Aug 19, 2024


    Chicago Way w/John Kass (08/19/24): To kick of the DNC in Chicago, the co-founder of RealClearPolitics, Tom Bevan, is here to preview his teams daily broadcasts on SiriusXM and discuss how the City of Big Shoulders will handle the influx of Democrats & protestors. Plus, Kasso wonders if anyone remembers the ‘wood shampoo’ of ’68? […]

    Chicago Way w/John Kass: Palikari IV – Legacy

    Play Episode Listen Later Aug 12, 2024


    The Palikari Project: Part IV – Legacy | As the curtain comes down on the Palikari Project, our hero returns home to his family’s village for the first time in almost 40 years with his sons, John, Peter, & Nick. We also get insight into what the boys were experiencing as twenty-somethings seeing their father’s […]

    Chicago Way w/John Kass: Palikari III – Civil War, Family, and a New World

    Play Episode Listen Later Aug 5, 2024


    The Palikari Project: Part III – Civil War & a Fresh Start | Toward the end of WWII, countries coming out from under the evil rule of The Axis were often were left to pickup the pieces of the decimated lives that once were. In Greece, that was turmoil was compounded by the rise of […]

    Chicago Way w/John Kass: Palikari pt.2 – Commies, Nazis, and Truman the Mule

    Play Episode Listen Later Jul 30, 2024


    The Palikari Project: Part II – Occupation & Communists | In occupied Greece during WWII, life for families was tough enough with a ruling foreign force of fascists & Nazis controlling everyday life but the real danger was the communists from within and their campaign of violence & fear. This is the story of Spyros […]

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