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From 15 epsHost
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Recent episodes
Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016
Jun 22, 2026
Chicago Way w/John Kass: What we don’t talk about says a lot
Jun 15, 2026
Chicago Way w/John Kass: Reissue – Episode #1 from January of 2016
Jun 8, 2026
Chicago Way w/John Kass: Does Mayor Brandon Johnson even want to run again?
May 31, 2026
Chicago Way w/John Kass: Summer is for the brave
May 26, 2026
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/22/26 | Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016 | Chicago Way w/John Kass (06/22/26): Re-Issue: Episode #6 from 02/10/206. Cartoonist Scott Stantis joins John Kass & Jeff Carlin to discuss what turns out to be the end of Rahm Emanuel’s tenure as Chicago Mayor, the 2016 primary season featuring Hillary Clinton vs. Bernie Sanders & Donald Trump vs. establishment everything, and meet two drivers […] | — | ||||||
| 6/15/26 | Chicago Way w/John Kass: What we don’t talk about says a lot | Chicago Way w/John Kass (06/15/26): John Kass & Jeff Carlin are together to talk about the things we don’t talk about when violence happens, how Chicago Democrats let the Bears go to Indiana to save face, and why the Obama Presidential Center allegedly owes people money, already. Plus, Kasso remembers the first time meeting his […] | — | ||||||
| 6/8/26 | Chicago Way w/John Kass: Reissue – Episode #1 from January of 2016✨ | hat controversylocal TV news+4 | Will LeeJeff Carlin | — | — | Chicago WayJohn Kass+5 | — | — | |
| 5/31/26 | Chicago Way w/John Kass: Does Mayor Brandon Johnson even want to run again?✨ | Chicago politicsBrandon Johnson+3 | Jeff CarlinRay Lopez | Chicago Way | — | Brandon JohnsonRay Lopez+3 | — | — | |
| 5/26/26 | Chicago Way w/John Kass: Summer is for the brave✨ | braverygang violence+3 | Jeff Carlin | — | Chicago | Chicagogang wars+3 | — | — | |
| 5/18/26 | Chicago Way w/John Kass: Don’t (bleep) with a pit bull’s reputation✨ | politicsChicago mayoral race+3 | Jeff CarlinPaul Vallas | Chicago Public SchoolsPhiladelphia+1 | Chicago | ChicagoPaul Vallas+4 | — | — | |
| 5/11/26 | Chicago Way w/John Kass: Hopium and the well-dressed chili powder thief✨ | Chicago politicsObama Presidential Center+3 | Jeff Carlin | Obama Presidential CenterWalgreens | — | ChicagoObama Presidential Center+3 | — | — | |
| 5/4/26 | Chicago Way w/John Kass: ‘Tips’ for Mother’s Day✨ | tippingMother's Day+3 | Jeff CarlinJimmy Banakis | JohnKassNews.com | — | tippingMother's Day+5 | — | — | |
| 4/27/26 | Chicago Way w/John Kass: A different time in D.C.✨ | Chicago newspolitics+3 | Jeff Carlin | Chicago Police | — | Chicago PoliceWhite House Correspondents’ Dinner+3 | — | — | |
| 4/20/26 | Chicago Way w/John Kass: On the hunt for politicization in U.S. intelligence✨ | U.S. intelligencepoliticization+3 | Nicholas S. Kass | American ConservativeU.S. government+2 | — | U.S. intelligencepoliticization+3 | — | — | |
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| 4/13/26 | Chicago Way w/John Kass: A time for reflection✨ | reflectionnews+3 | Jeff Carlin | JohnKassNews.com | — | John KassJeff Carlin+5 | — | — | |
| 4/6/26 | Chicago Way w/John Kass: Trump’s Iranian tightrope✨ | Trump's legacyIran war+3 | Charles Lipson | University of Chicago | Iran | TrumpIran+5 | — | — | |
| 3/30/26 | Chicago Way w/John Kass: Alders warn us ‘wrong place, wrong time’ but they created this✨ | violent crimeDemocrats+4 | Rafael Mangual | Manhattan InstituteCity Journal | Chicago | Chicagoviolent crime+4 | — | — | |
| 3/23/26 | Chicago Way w/John Kass: A blueprint for getting involved in the Republic✨ | political engagementlocal elections+3 | Tom Morrison | CandidateMasterclass.com | — | politicselections+3 | — | — | |
| 3/17/26 | Chicago Way w/John Kass: Authoritarianism cometh from Springfield✨ | authoritarianismcivil rights+3 | James R. BrownBrendan Philbin | Liberty Justice CenterIllinois Supreme Court | — | authoritarianismcivil rights lawsuit+3 | — | — | |
| 3/10/26 | Chicago Way w/John Kass: Dan Proft responds to Darren Bailey’s whining✨ | Illinois governor's raceRepublican primary+3 | Dan Proft | WIND AM 560 | Illinois | Illinois governor's raceDarren Bailey+4 | — | — | |
| 3/3/26 | Chicago Way w/John Kass: Back from the brink, again✨ | return from absenceappreciation+3 | Jeff Carlin | JohnKassNews.comFacebook | — | John KassJeff Carlin+3 | — | — | |
| 2/23/26 | Chicago Way w/John Kass: Winter returns on a good horse in the snow | Chicago Way w/John Kass (02/23/26): Nicholas Kass steps in for Jeff Carlin & John Kass as illness plagues the Kasso-sphere to present one of his favorite JohnKassNews.com columns, Riding a Good Horse in the Snow, Part 2. Nick is a regular contributor and, most notably, a retired U.S. Foreign Service officer, diplomat, and Intelligence expert […] | — | ||||||
| 2/16/26 | Chicago Way w/John Kass: Keeping Chicago’s Irish heritage alive | Chicago Way w/John Kass (02/16/26): Mike “Houli” Houlihan, a well-known Irish-American actor, filmmaker, stand-up comedian, and former Chicago Sun-Times columnist, joins Jeff Carlin while John Kass regains his voice. Houli has a new piece on JohnKassNews.com and is always working on multiple projects at Hibernian Media. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, […] | — | ||||||
| 2/9/26 | Chicago Way w/John Kass: Quantifying trust | Chicago Way w/John Kass (02/09/26): Charles Lipson is back playing pinch-hitter for John Kass, who lost his voice educating bright young minds at Hillsdale College, and joins Jeff Carlin with a dive into how we quantify trust. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X (Twitter). Tell your friends about us. […] | — | ||||||
| 2/2/26 | Chicago Way w/John Kass: A lesson from Princeton on the summer of 1861 | Chicago Way w/John Kass (02/02/26): RealClear Politics’ Tom Bevan is here to discuss how we got ourselves to tenuous climate in American politics, what we can learn from his Princeton senior thesis, and why Don Lemon is going to be okay, even if he tells you different. Plus, Kasso wonders if there is a more […] | — | ||||||
| 1/26/26 | Chicago Way w/John Kass: On the brink | Chicago Way w/John Kass (01/26/26): Retired police chief Tom Weitzel (Riverside) joins John Kass & Jeff Carlin to talk about his work with Awake Illinois to stop SB2820 (Introduced by Sen. Laura Fine [D-Glenview]) from being passed. SB2820 would ban anyone who previously worked with Immigration and Customs Enforcement (ICE) from being a law enforcement […] | — | ||||||
| 1/19/26 | Chicago Way w/John Kass: Still no compassion from the media or politicians for a father’s loss | Chicago Way w/John Kass (01/19/26): To mark the tragic anniversary of his daughter’s death, 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 […] | — | ||||||
| 1/12/26 | Chicago Way w/John Kass: The good, the bad, and the ugly of the Illinois’ judiciary | Chicago Way w/John Kass (01/12/26): Thom Serafin, long-time political strategist, Communicator in Chief of Serafin & Associates, & newly collaborating with Mercury Illinois, joins John Kass & Jeff Carlin with some much needed perspective on who are the Cook County Bar Association & the Chicago Council of Lawyers, and why are they upset over a […] | — | ||||||
| 1/5/26 | Chicago Way w/John Kass: Charles Lipson looks at how 2026 might unfold | Chicago Way w/John Kass (01/05/26): This week, Charles Lipson joins John Kass & Jeff Carlin to start off the new year. 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 […] | — | ||||||
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