Hillsdale College Podcast Network Superfeed
Episode: Journalism “The Chicago Way”
Date: March 27, 2026
Host: Scott Bertram
Guests: John Kass (legendary Chicago journalist), Dr. Matt Meehan (Associate Dean, Hillsdale in D.C.)

Episode Overview

This episode of the Radio Free Hillsdale Hour explores the intersection of journalism, politics, and culture, focusing on the unique political climate in Chicago ("the Chicago Way"), the decline of trust in mainstream media, and reflections on the shifting purpose and perception of children in American society. Legendary Chicago journalist John Kass shares his insights on the ruthlessness of Chicago politics, the ideological shifts in media, and his own departure from the Chicago Tribune. In the second segment, Dr. Matt Meehan discusses the deeper civic and transcendent purposes of children beyond mere economic considerations.

Part 1: John Kass on "The Chicago Way" and the State of Journalism

The Chicago Way Defined

• The phrase "The Chicago Way" is derived from the film The Untouchables, symbolizing a ruthless, retaliatory approach to politics and crime:

  “He takes a knife, you grab a gun. He sends one of yours to the hospital, you send one of his to the morgue. That's the Chicago Way.”
  — John Kass quoting the film (01:59)

• Kass clarifies that while not personally ruthless, this ethos is deeply embedded in Chicago’s political culture.

Kass’s Exit from the Tribune

• Kass recounts how his departure in 2021 was prompted by Tribune union backlash over his columns on George Soros and the consequences of decarceration policies during the "summer of love" unrest:

  "They demanded that I be removed from page two. They demanded that I attend what anyone who studies communism would know of as a struggle session...My only response to an editor was, I'm not apologizing."
  — John Kass (04:14)

• He criticizes the Tribune’s rationale for his removal:

  “They had to say, the readers are not sophisticated enough to realize what's written as opinion on page two...They had to say the readers couldn't figure out what was news and what was opinion anymore.”
  — Scott Bertram (05:32)

• Kass reflects on the broader ideological shift:

  “This is the left. And it started, I think, when they created Barack Obama as a plaster saint...that’s how newspapers lost their way.”
  — John Kass (06:14)

Going Independent

• Kass notes the benefits of independence:

  “I don't have any insect leaning over my shoulder telling me what to think or what to say.”
  — John Kass (07:08)

Decline of Trust in Media

• Kass pinpoints the deification of Barack Obama as a turning point for media trust, explaining:

  "They were talking about him as Pegasus rising from sea foam...he was a phony and they didn’t want this. Partly why the left in Chicago hated me so much. I didn’t buy into the whole Barack Obama is a demigod."
  — John Kass (07:46)

• On media bias and the Russia investigation:

  “We had a president who ordered...the CIA chief to...put forward a different story that...Trump was an agent of the Russians. The New York Times and the Washington Post each received Pulitzer Prizes...forever the Pulitzer Prize...is not worth anything now. And that's why people lost faith.”
  — John Kass (09:05)

Chicago Politics: From the Dailys to the Teachers Union

• Bertram and Kass discuss the shift of power:

  “Chicago for years politically was ruled by the dailies and Mike Madigan...With their demise, a power vacuum existed in Chicago. Into that stepped the Chicago Teachers Union.”
  — Scott Bertram (11:41)

• Kass details their rise:

  “They are the Democratic Party now. They decide whether you’re going to succeed as a candidate or not. Everyone kisses their behind if you want to run in those districts.”
  — John Kass (12:14)

Socialist Experiments and Urban Decline

• On the consequences of “socialist mayors”:

  “Absolute failure and anarchy, where people are attacked on the way home from work...The public transportation...is the poorest of us. They're on the L and they're, they're subject to the barbarism of the Democratic Party that does not incarcerate the violent.”
  — John Kass (13:57)

• On the chasm between leadership and regular people:

  “Chicago is still a blue collar town and common sense is prided. The people of Chicago are not intimidated by fancy pants talk.”
  — John Kass (15:52)

Memorable Columns and Reflections

• Bertram shares his favorite Kass column, highlighting its humanity.

• Kass’s most treasured pieces:

  “The first one was about my father...And the other column is one that I rewrite every year at Christmas Eve, it's called O Holy Night...taken from the petitions of the Greek Orthodox liturgy.”
  — John Kass (17:55)

• On the spiritual role of places like Hillsdale:

  "Hillsdale represents in the Dark Ages...such places with high walls that students can come to safely and study. That's what I see is Hillsdale."
  — John Kass (19:55)

Notable Quotes & Timestamps

• Defining the Chicago Way — John Kass (01:59)
• Ruthlessness in Politics — John Kass (02:45)
• On Struggle Sessions and Refusing to Apologize — John Kass (04:14)
• On Ideological Union Control — John Kass (06:14)
• Media Lost Its Way with Obama — John Kass (07:46)
• On the Pulitzer Prize and Media Bias — John Kass (09:05)
• Teachers Union as Political Kingmakers — John Kass (12:14)
• Consequences of Urban Socialist Policies — John Kass (13:57)
• Distance between Elites and Regular People — John Kass (15:52)
• Favorite Columns and Faith — John Kass (17:55)
• Hillsdale as a Bastion of Learning — John Kass (19:55)

Part 2: Dr. Matt Meehan on the Higher Purpose of Children in American Society

The Moral and Civic Value of Children

• Opening with Washington’s grief for his stepdaughter:

  "He actually adopted Patsy Custis, and...became her father and loved her dearly...when she passed away...he was grievously wounded.”
  — Dr. Matt Meehan (24:00)

• Meehan answers why children are more than future economic contributors:

  “It's basically treating children as adults without any kind of recognition of their relationship or their personality as sons and daughters...Once you expand the...Republican experience beyond the workplace...you see the benefits of children go far beyond the economic man."
  — Dr. Matt Meehan (25:24)

Complexa Caritatis: The Network of Loves

• On the social fabric, forged by family and community:

  “When a child enters the world, relationships are instantly made...These relationships...are what foster a sense of givenness and gratitude, which then is the engine for why you would give back. That gratitude comes from this interwoven network of loves which comes through the child.”
  — Dr. Matt Meehan (27:03)

The Founders and Civic Life

• The founding generation saw child-rearing as essential training for civic virtue:

  “Raising a next generation is this refresher course on governance...you slowly open the aperture unto adulthood...preliminary analog things that the citizenry need to be doing...help them choose good representatives.”
  — Dr. Matt Meehan (29:35)

Education Beyond Economic Preparation

• “They need a liberal arts education...with a transcendent view...and a very serious civic component. Law is a liberal art much forgotten in our day.”
  — Dr. Matt Meehan (31:46)

On Falling Birthrates and Meaning

• Declining regard for children is about meaning, not just economics:

  “There is a kind of sad carelessness that sets in where it's like, what does it even matter?...Free government...doesn't really matter. We're all adults, so who cares? Eat, drink and be merry for tomorrow we'll die. The transcendent is gone.”
  — Dr. Matt Meehan (33:40)

• Utopian policies cannot replace private goods:

  “An entire citizenry of single people is much more liable to utopian crazy political adventure.”
  — Dr. Matt Meehan (35:32)

On Pronatalist Policies

• Material incentives have limited impact:

  “They are marginal benefits. I think what people need to be paid in is not just physical benefits...but honor. The family must be honored again...we need to re-educate ourselves in the virtues."
  — Dr. Matt Meehan (38:05)

• Citing personal example:

  “I will confess on the radio, I didn't own a home until I held my eighth child in a NICU with a hole in her heart. That's when I bought my first home...I will suffer for family and I'll put family first.”
  — Dr. Matt Meehan (39:34)

Notable Quotes & Timestamps

• On Treating Children as Economic Units — Dr. Matt Meehan (25:24)
• The Complex of Charity in Civic Life — Dr. Matt Meehan (27:03)
• Founders' Perspective on Children & Governance — Dr. Matt Meehan (29:35)
• The Meaning Crisis & Birthrates — Dr. Matt Meehan (33:40)
• On Family Honor and Virtue — Dr. Matt Meehan (38:05)
• Personal Sacrifice for Family — Dr. Matt Meehan (39:34)

Conclusion

This episode offers a rich exploration of journalism, governance, culture, and the family as seen through the eyes of two insightful guests. John Kass provides a candid, often evocative account of what makes Chicago politics brutally unique, how media institutions lost public trust, and the hard-won liberty of independent journalism. Dr. Matt Meehan reframes the American conversation about children, urging listeners to recognize the foundational, transcendent roles that family and civic love play in preserving republican self-government.

For More:

• Visit johncassnews.com and the Chicago Way podcast
• Read Dr. Matt Meehan’s essay at heritage.org
• New episodes at podcast.hillsdale.edu

This summary excludes advertisements and other non-content sections. It preserves original viewpoints and tone, provides useful quotes and guidance for further exploration, and is intended for those seeking a substantive understanding of the episode.