The Chicago Way

Chicago Way w/John Kass (09/01/25): Newly minted candidate for Illinois Governor Ted Dabrowski of Wirepoints joins John Kass & Jeff Carlin to lay out his plan for convincing the center left & independent voters of the state to help him beat Gov. JB Pritzker in next year’s election. Plus, Kasso wonders if this is the […]

Chicago Way w/John Kass (09/01/25): This week, former Cook County and federal prosecutor Bob Milan joins John Kass & Jeff Carlin to talk about his original plan from 10 years ago to bring in National Guard troops to tamp down the weekly number of shootings in Chicago and how this strategy might work today. Plus, […]

Chicago Way w/John Kass (08/25/25): Glenview native Joe Abraham joins John Kass & Jeff Carlin to talk about his gut-wrenching experience losing his daughter Katie when she was killed in a hit-and-run crash, allegedly caused by a Guatemalan national who was in the country illegally and is suspected of driving under the influence, Julio Cucul […]

Chicago Way w/John Kass (08/18/25): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin with a look at how President Barack Obama’s misdeeds compare to Richard Nixon, what candidate for mayor Zohran Mamdani means for NYC, and whether voters will ever get out from the stranglehold of the Iron Triangle deception created […]

Chicago Way w/John Kass (08/11/25): This week, John Kass & Jeff Carlin tackle JB Pritzker’s hypocrisy when it comes gerrymandering, evidence that President Barack Obama was trying to convince people Russia got Trump elected in 2016 -even though we know they didn’t, and look at why dreams of living on the Moon or Mars are […]

Chicago Way w/John Kass (08/04/25): Chicago Alderman Brendan Reilly (42nd) joins John Kass & Jeff Carlin to announce that his circulating petitions and seriously considering running against Cook County Board President Toni Preckwinkle. Ald. Reilly talks about wanting to course correct years of democratic socialist policies that have left the county broke & bloated. Plus, […]

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, […]