The Chicago Way

Chicago Way w/John Kass (03/18/24): On this edition, John Kass and Jeff Carlin welcome John’s younger brother, Nicholas Spyridon Kass, a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on security matters. For this conversation, Nick offers up deeper insights into American diplomacy and military failings in Syria […]

Chicago Way w/John Kass (03/15/24): To celebrate the Feast of Saint Patrick, 1st generation Southside Irishman & English teacher Pat Hickey joins the podcast to discuss his family’s history on the island, the great Irish habit of saving civilization from itself, and Two Gored Bulls of Ireland. Plus, Kass & Carlin take Steve Cochran to task […]

Chicago Way w/John Kass (03/11/24): On this edition, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson, joins John Kass and Jeff Carlin with a look at the race for the White House, Fani Willis’ legal woes, and President Biden’s two-state solution – Michigan and Minnesota. Plus, Kasso wonders […]

Chicago Way w/John Kass (03/07/24): Joining the conversation today with John Kass & Jeff Carlin is Erin Geary, who tapped into her 30+ years as of experience as an educator in Chicago Public Schools, the Archdiocese, and beyond to write a great piece entitled “No Chicago Rebrand Needed, Education and Public Safety Above Cheap PR”, […]

Chicago Way w/John Kass (03/04/24): Joining John Kass & Jeff Carlin on this episode is Leland Vittert, the host of On Balance w/Leland Vittert and D.C. correspondent for NewsNation, to discuss how Super Tuesday might impact the future of Nikki Haley’s campaign, possible VP picks for Donald Trump, and ‘photo-op food drops’ in Gaza by […]

Chicago Way w/John Kass (03/01/24): 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 a brilliant piece he wrote titled “America Works. DEI Doesn’t.” Pastor Brooks also explains how politicians like Chicago Mayor Brandon Johnson abandon his cause after they get […]

Chicago Way w/John Kass (02/26/24): RealClear Politics’ Tom Bevan looks at the future of Nikki Haley’s campaign, discusses what a third-party candidate means for Donald Trump & Joe Biden, and celebrates the debut of “RealClearPolitics” on SiriusXM. Plus, Kasso wonders if Heidi Przybyla has ever read the Declaration of Independence or the Constitution? Check out more […]

Chicago Way w/John Kass (02/23/24): News Director for Florida’s Voice, Anita Padilla is back with a breakdown of why the citizens of Chicago are coming out in droves to give Mayor Brandon Johnson a piece of their mind as ‘migrants’ pour into the countries’ major cities, disrupting everyday life. Plus, Kasso wonders if Cook County […]

Chicago Way w/John Kass (02/19/24): One this edition, former Chicago Tribune editor & veteran of the Cook County State’s Attorney’s office, John Gorman talks about his first book Death Before Life and why the race for State’s Attorney is important for Chicagoans. Gorman joins John Kass & Jeff Carlin for a great discussion and offers […]

Chicago Way w/John Kass (02/16/24): Austin Berg is here from the Illinois Policy Institute with a breakdown of how things are going at the Chicago Teachers Union controlled City Hall. Austin joins John Kass & Jeff Carlin with a look at how Cook County President Toni Preckwinkle is attempting to distance themselves from Mayor Brandon […]

Chicago Way w/John Kass (02/12/24): 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 Kass. The younger Kass breaks down what happens when the ‘deep […]

Chicago Way w/John Kass (02/05/24): On episode 426, Senior Technical Producer & life-long southside resident of Chicago Brian Althimer joins John Kass & Jeff Carlin to share his perspective as someone who was born Englewood and has seen how crime & disinvestment have changed the South Side of the city over his lifetime. Plus, Kasso […]

Chicago Way w/John Kass (01/29/24): This week, Amber Duke (Athey) joins John Kass & Jeff Carlin to discuss her new book, ‘The Snowflakes’ Revolt: How Woke Millennials Hijacked American Media.’ Amber also talks about being cancelled at WMAL and how newsrooms across the country have lost their credibility after allowing ‘Snowflakes’ to press their ill-conceived […]

Chicago Way w/John Kass (01/22/24): RealClear Politics’ Tom Bevan breaks down what Florida Governor Ron DeSantis’s campaign got foolishly wrong, how the GOP ’24 primary is really a Vice Presidential primary, why Nikki Hailey will never be Donald Trump’s VP pick (but Elise Stefanik or Tim Scott will be), and what happens when liberals realize […]

Chicago Way w/John Kass (01/15/24): This week, hometown reporter Anita Padilla talks about her time covering Chicago and what is next as she embarks on a new role as News Director for Florida’s Voice. Plus, John Kass & Jeff Carlin wonder if Mayor Brandon Johnson is cracking from the pressure of membership in Chicago’s clown-carpool […]