The Chicago Way

Chicago Way w/John Kass (07/28/25): This week, Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin to discuss how Mayor Brandon Johnson has let flooding plague the city, year after year, while he spends time picking fights with President Donald Trump. Ray also wonders if intellectual curiosity is dead and why Chicago’s voter rolls seem […]

Chicago Way w/John Kass (07/21/25): On this episode, Ted Dabrowski of Wirepoints.com joins John Kass & Jeff Carlin to highlight how Governor JB Pritzker is delusional about Illinois’ status as an ‘economic powerhouse’ and to warn the voters of New York City about the perils of electing unserious socialists. Plus, Kasso offers a hat-tip to […]

Chicago Way w/John Kass (07/07/25): Charles Lipson joins John Kass & Jeff Carlin for this post Independence Day episode. 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, […]

Chicago Way w/John Kass (06/30/25): On a HOT summer Sunday, John Kass & Jeff Carlin head out to the first annual Sicilian Summer Block Party in the Dunning neighborhood to break bread and enjoy some entertainment. Along the way, fans of John’s share stories about what the Chicago Way means to them. Plus, Kasso tells […]

Chicago Way w/John Kass (06/23/25): On this episode, revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin with a look at the history of the ‘Chicago Way’ -alderman, committee men, cops, etc. shaking down small biz- and how it personally has impacted his family through the generations. Plus, Kasso wonders if business as […]

Chicago Way w/John Kass (06/16/25): This week, John Kass & Jeff Carlin are pleased to welcome Sal Camarda from Joseph’s Finest Meats to talk about his family’s tradition of bringing the best quality meats, sausages, and more to Chicago. Sal, along with his brother Ben, are second generation proprietors and enjoy being part of the […]

Chicago Way w/John Kass (06/09/25): Prof. Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago (whose writings can be found in the Spectator, Spectator World, The Telegraph, and more), is here to explain why Democrats keep ending up on the wrong side of ’80/20 problems’ and how American culture […]

Chicago Way w/John Kass (06/02/25): This week, John Kass & Jeff Carlin discuss the merits of President Donald Trump commutating the federal sentence of notorious gang kingpin Larry Hoover and feds seeking to put former Illinois Speaker of the House Mike Madigan in jail for 12 years at the age of 83. Plus, Kasso urges everyone […]

Chicago Way w/John Kass (05/27/25): This week, John Kass tries to get to the bottom of Jeff Carlin’s bad mood by sharing stories from his weekend in the city celebrating his wedding 39th wedding anniversary. Plus, Kasso wonders if his love for Chicago can ever be redeemed. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, […]

Chicago Way w/John Kass (05/19/25): RealClear Politics’ Tom Bevan is here to discuss James Comey selling seashells by the seashore and what could be considered one of the greatest scandals in presidential history, the cover-up of Joe Biden’s health problems. John Kass & Jeff Carlin also ask Tom about Rahm Emanuel facing off against JB Pritzker in […]

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 (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 (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 (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, [&#8230...

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 (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...

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 (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 (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 (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 (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 (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 (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 (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 (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 […]