The Chicago Way

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 […]

Transcribed - Published: 29 April 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 [email protected], or Facebook, […]

Transcribed - Published: 20 April 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. […]

Transcribed - Published: 14 April 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 […]

Transcribed - Published: 7 April 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 […]

Transcribed - Published: 31 March 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 […]

Transcribed - Published: 24 March 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 […]

Transcribed - Published: 17 March 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 […]

Transcribed - Published: 10 March 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 [email protected], […]

Transcribed - Published: 3 March 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 […]

Transcribed - Published: 24 February 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 […]

Transcribed - Published: 17 February 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 […]

Transcribed - Published: 10 February 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 […]

Transcribed - Published: 3 February 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 […]

Transcribed - Published: 27 January 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 […]

Transcribed - Published: 20 January 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 […]

Transcribed - Published: 13 January 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 […]

Transcribed - Published: 6 January 2025

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 […]

Transcribed - Published: 30 December 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 […]

Transcribed - Published: 23 December 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 […]

Transcribed - Published: 16 December 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 […]

Transcribed - Published: 16 December 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, […]

Transcribed - Published: 9 December 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 […]

Transcribed - Published: 2 December 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, […]

Transcribed - Published: 25 November 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 […]

Transcribed - Published: 18 November 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 […]

Transcribed - Published: 11 November 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 […]

Transcribed - Published: 4 November 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 […]

Transcribed - Published: 29 October 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 […]

Transcribed - Published: 21 October 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 […]

Transcribed - Published: 14 October 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 […]

Transcribed - Published: 7 October 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 […]

Transcribed - Published: 30 September 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, […]

Transcribed - Published: 23 September 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 […]

Transcribed - Published: 16 September 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 […]

Transcribed - Published: 9 September 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 […]

Transcribed - Published: 3 September 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 […]

Transcribed - Published: 26 August 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 team’s 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? […]

Transcribed - Published: 19 August 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 […]

Transcribed - Published: 12 August 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 […]

Transcribed - Published: 5 August 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 […]

Transcribed - Published: 30 July 2024

The Palikari Project: Part I – Rizes | Thirty-five years ago in Oak Lawn, John Kass & his brother Nicholas set a card table with coffee, cigarettes, & a tap recorder, hoping to capture their family’s story from a primary source, their father, Spyros John Kass. The tapes were part of an art project John’s […]

Transcribed - Published: 22 July 2024

Chicago Way w/John Kass (07/16/24): Nicholas Kass, a retired American diplomat with over 30-years of experience focused on Aegean/Eastern Mediterranean issues, joins his brother John Kass & Jeff Carlin to break down what happens after an attempt on Donald Trump’s life was made and how the ‘Deep State’ will respond. Plus, Kasso won’t forget the […]

Transcribed - Published: 16 July 2024

Chicago Way w/John Kass (07/11/24): After a violent holiday weekend that saw over 100 people shot and 20 killed, Garry McCarthy -former Chicago Police Superintendent and current Chief of Police for Willow Springs, IL -join John Kass & Jeff Carlin for a discussion about why the city has seen such a spike in violent crime […]

Transcribed - Published: 12 July 2024

Chicago Way w/John Kass (07/01/24): To celebrate Independence Day and make sense of the debate, SCOTUS rulings, and more, Charles Lipson -the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago- joins John Kass and Jeff Carlin. Plus, Kasso has a recipe for catching wild hogs, just in-time for the grill. […]

Transcribed - Published: 1 July 2024

Chicago Way w/John Kass (06/21/24): This week, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast Thom Serafin joins John Kass & Jeff Carlin to talk June’s Serafin Power Poll, what summer in Chicago will look like with the DNC, NASCAR, Lolla, & more taking over, and why President Joe Biden’s […]

Transcribed - Published: 21 June 2024

Chicago Way w/John Kass (06/14/24): Regular contributor to JohnKassNews.com Michael Ledwith (@ledwith_michael) joins John Kass & Jeff Carlin so they can learn more about the man behind great columns like “An Irish Fable” and of course “Part 2″ and to discuss his latest, “As DNC Nears, Do Chicago Cops Have Any Leverage to Do Their […]

Transcribed - Published: 14 June 2024

Chicago Way w/John Kass (06/07/24): Nicholas Kass, a retired American diplomat with over 30-years of experience focused on Aegean/Eastern Mediterranean issues, joins his brother John Kass & Jeff Carlin to talk about modern liberalism pulling the U.S. into a banana republic and how Kemalists wrote their playbook. Plus, Kasso wonders why Jussie Smollett’s hoax went […]

Transcribed - Published: 7 June 2024

Chicago Way w/John Kass (05/31/24): RealClear Politics’ Tom Bevan join John Kass & Jeff Carlin with a look at how Donald Trump’s legal issues hamper (or don’t) his chances in the general election come November, if sanity can ever be regained in the arena of political discourse, and will the Republic rebound from the weaponization of […]

Transcribed - Published: 31 May 2024

Chicago Way w/John Kass (05/24/24): John Kass has an update on his health and explains why Nikki Haley could cause him to become a ‘commie.’ Jeff Carlin explains the science behind beer temperatures and Kasso celebrates his wife Betty on the anniversary of their marriage with the story of being left gobsmacked the moment they […]

Transcribed - Published: 24 May 2024