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 the tale of the podcast’s origin story.

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 usual will ever change?

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 city’s vibrant food scene. Plus, Kasso has a tip about a special meet & greet event coming up at the first annual Sicilian Summer Block Party on the city’s northwest side.

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 has come to a fork in the road that will decide the fate of generations to come. Plus, Kasso wonders why SEIU leaders are at the forefront the chaos happening on the streets of Los Angeles.

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 to take some time and enjoy the outdoors while we still can.

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 a political contest. Plus, Kasso wonders who was really running the White House during Biden’s tenure?

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 at what it would take for him to run for mayor. Plus, Kasso wonders if there is a cure for Chicago’s dying legacy media?

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 answer for his criticisms of the governor. Plus, Kasso wonders if anyone has noticed the similarities between Illinois & Soviet-era Romania?

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.

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 latest “hot rhetoric” means for his political future. Plus, Serafin’s April Power Poll asks the question: “With which notable Illinois political heavyweights would you want to have dinner?”

Check out more from Kass at JohnKassNews.com or contact me at [email protected], or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! And read writings from John’s brother Nick for the American Conservative here and here.