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    News

    The Chicago Way

    Mild mannered Chicago Tribune columnist John Kass and WGN Radio’s Jeff Carlin explore the week in news, politics and other thngs done the Chicago Way in this WGN Plus podcast from WGN Radio in Chicago.

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    Copyright: © WGN Plus, All Rights Reserved

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    Latest Episodes:
    Chicago Way w/John Kass: Dan Proft responds to Darren Bailey’s whining Mar 10, 2026
    Show notes

    Chicago Way w/John Kass (03/10/26): Dan Proft, co-host of “The Morning Answer” radio program 5-9 a.m. on WIND AM 560, is this week’s guest joining John Kass & Jeff Carlin to discuss the Illinois governor’s race, specifically the Republican primary that has seen second-time candidate Darren Bailey take umbrage with Dan being paid to work on behalf of first-time candidate, Ted Dabrowski. Plus, Kasso wonders why the Chicago Tribune isn’t endorsing anyone in the Republican primary?

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/8023640/8023640_2026-03-10-131340.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

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    Kass: When good food is simple, what more do you need?

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    Chicago Way w/John Kass: A hooley of a good time

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    Kass: Mayor Brandon Johnson and the 40 flies

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    Kass: Chicago Flips Red’s candidate for mayor

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    Chicago Way w/John Kass: Back from the brink, again Mar 03, 2026
    Show notes

    Chicago Way w/John Kass (03/03/26): John Kass is back. John joins Jeff Carlin to talk about what’s kept him away and what’s next. Plus, Kasso wonders if we really appreciate what we have?

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/8008003/8008003_2026-03-03-191303.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

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    Kass: When good food is simple, what more do you need?

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    Chicago Way w/John Kass: A hooley of a good time

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    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: Winter returns on a good horse in the snow Feb 23, 2026
    Show notes

    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 with 30+ years of experience in the field. Enjoy.

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7992210/7992210_2026-02-23-181410.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

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    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: Keeping Chicago’s Irish heritage alive Feb 16, 2026
    Show notes

    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, or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7978541/7978541_2026-02-16-175341.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

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    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: Quantifying trust Feb 09, 2026
    Show notes

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7965043/7965043_2026-02-09-184043.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: A lesson from Princeton on the summer of 1861 Feb 02, 2026
    Show notes

    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 important prize for real journalism than The Samizdat Prize?

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7952001/7952001_2026-02-02-214001.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: On the brink Jan 26, 2026
    Show notes

    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 officer in Illinois. Plus, Kasso wonders if there is a way to step back from all-out civil war that doesn’t involve bowing before the leftists?

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7936515/7936515_2026-01-26-205715.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: Still no compassion from the media or politicians for a father’s loss Jan 19, 2026
    Show notes

    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 is suspected of driving under the influence. In the year since Joe’s family was torn apart, a lot has happened, including ‘Operation Midway Blitz,’ some shady dealings by Chicago ‘Paper’ reporters, and a myriad of national coverage. But missing from this coverage is any support from the elected officials of Illinois and coverage by the local media.

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7923605/7923605_2026-01-19-214405.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: The good, the bad, and the ugly of the Illinois’ judiciary Jan 12, 2026
    Show notes

    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 JohnKassNews.com column & Chicago Way Podcast. (Hat tip to CWB for covering this fiasco) Plus, Kasso wonders if Chicagoans can come together over their hatred for the Packers?

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7912338/7912338_2026-01-12-224138.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
    Chicago Way w/John Kass: Charles Lipson looks at how 2026 might unfold Jan 05, 2026
    Show notes

    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 the docket, US actions in Venezuela and its implications in the region concerning Cuba. Also, up for discussion is how Gov. Tim Walz and Minnesota’s fraud problem is going to impact 2026 midterms. Plus, Kasso tells the story of young state senator from Illinois trying to stay above the fray.

    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. Join the great adventure. Subscribe today!

    https://serve.castfire.com/audio/7895708/7895708_2026-01-05-221308.64kmono.mp3
    Follow Everything John Kass – JohnKassNews.com
    Follow @John_Kass Follow @JPCarlin
    Download this episode here by using ‘Save As’ here
    Subscribe to The Chicago Way

    Recent Posts

    The Chicago Way with John Kass

    Chicago Way w/John Kass: The time is now for independent media in Illinois

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: When good food is simple, what more do you need?

    .cls-7{fill:#fff;fill-rule:evenodd}

    Chicago Way w/John Kass: A hooley of a good time

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Mayor Brandon Johnson and the 40 flies

    .cls-7{fill:#fff;fill-rule:evenodd}

    Kass: Chicago Flips Red’s candidate for mayor

    .cls-7{fill:#fff;fill-rule:evenodd} Click for more
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