By David Bittinger

September 10th, 2026

You’ll probably recognize much of the Chicago newspaper history recounted here. Some of you might feel you could write your own version of this piece.

Every day of my childhood started with a Chicago Tribune on the kitchen table. It seemed a gateway from the early-Disneyfied bubble of my pleasant suburb Glen Ellyn to a grand city of skyscrapers and action.

I learned to read before kindergarten, partly because I loved books but more because I wanted to read reports of White Sox games. Little Louie and Nellie and big old Comiskey Park were right there in the last section behind the masthead motto THE WORLD’S GREATEST NEWSPAPER. That status impressed a five-year-old.

The motto was withdrawn late in the Ford administration. Sic transit gloria mundi.

I liked David Condon’s “In the Wake of the News” column and his annual joke prediction of a World Series between the White Sox and Cubs. (In this 2026 season, that prospect seems less a joke than a warning of internecine Chicago anxiety attacks.)

While reading the Tribune daily, I also sought out Mike Royko columns in the Daily News until it folded in 1978, then in the Sun-Times. Royko quit the Sun-Times on January 10, 1984 after it was bought by a publisher he despised as a tabloid sensationalist. He “walked across Michigan Avenue” to the Tribune the same day, offering his new employer the faint praise “Mr. Murdoch doesn’t own this paper.”

Attracting many of the smart working-class readers who loved Royko, the Tribune broadened its base and increased its circulation advantage. The man was a deserving Pulitzer Prize winner with Chicago street cred. Though early identifying himself as a Democrat, he was always fiercely independent, the scourge of corrupt players and a major thorn in the Machine’s side.

Royko was now the Tribune’s page three champ, taking on Chicago’s connected heavyweights with powerful jabs that couldn’t be thrown by the city’s handful of Republicans.

I ate up 13 more years of Royko commentary. Then 1997 happened, with several losses from my perspective. Two happened within three days: Royko’s death at 64, then my father’s at 73. Painful losses, but never lost were the heard and read lessons of two men whose character, work, and sense of humor stayed with me. I felt lucky to have had these great Midwestern presences in my life.

Who could replace Royko, our Chicagoan in America’s edgy commentary tradition of Twain and Mencken? His work was a wonder of fearless reporting on the muscle flexers and the virtue peddlers. Could anyone else play that position?

Four months later the call-up for page three appeared, some guy named Kass. He better be good, I thought.

He sure was. JKN readers know later versions, but if you navigate through archives (and some paywalls) you can read / re-read great early versions of his takes on Christmas, beer can chicken, the Lovely Sicilian, the family-anchor mother, the Outfit, the Smarty-Pants Elite, Zeus the Wonderdog, and other wonders of Chicago nature.

Kass’ columns came from streets travelled by Royko, and were often, like Mike’s, more fun than a barrel of monkey-business aldermen (sent to prison). And Golden Moutzas arrived, raining down wise-guy justice.

But his columns were more rooted in the neighborhoods of principled social and political conservatism. And they inspired at least one other writer.

A number of my op-ed columns were published by the Tribune before and during Kass’ column there (also by the Washington Post, Los Angeles Times, and some other op-ed pages, if you’ll pardon the aside).

Minor as they were, my Tribune contributions were appreciated by the paper’s strong-minded, broad-minded Commentary Editor Marcia Lythcott. A black woman who became an Editorial Board member, her role would have been unimaginable during the old days of Colonel McCormick’s ownership. Growth at the Tower.

Starting in July, 2020, Kass’ days at the Tribune were numbered. The count started during a storm of in-office “goodthink” by fellow Tribune employees over Kass’ “thoughtcrime.” (Those two terms are from the eerily futuristic novel 1984 by a brilliant British writer — once a more conventional socialist — who in 1948 confronted the escalating disaster of all-powerful government.)

In two columns about Chicago’s descent into politically excused crime and increasingly corrupt governance, Kass named the sponsor of that slow-motion nightmare: international currency manipulator George Soros.

A leftist billionaire who despised the capitalist system he conned, Soros barely dipped into his fortune to elect criminal-friendly prosecutors and judges in Chicago and at least 74 other major American cities and distinct jurisdictions. Soros’ $2 million gift to Chicago was the re-election of Cook County’s criminally sympathetic State’s Attorney Kim Foxx.

In Foxx’s Soros-sponsored 2020 re-election, her opponent won suburban areas of Cook County, but she won overwhelmingly among Chicago voters who thought prison sentences were mean.

Kass wrote repeatedly about Foxx’s reign of anti-prosecution terror, including the most infamous one, the Jussie Smollett “This is MAGA Country” progressive fantasy crime. Special Prosecutor Dan Webb noted her “substantial abuses of discretion” in that case.

Kass’ accurate accounts of Soros’ advocacy for Chicago’s criminal population and of the city’s larger sinking ship enraged Tribune leftists who wanted Kass gone.

The times they were a-changing at “the paper” (as it’s been called at JKN with deserved irony) and in other papers. I’d noticed that the Tribune and other newspapers that had published me earlier seemed to have removed two editorial welcome mats: one for a sense that contrarian conservative opinion was valid, the other for a sense of humor.

Alden Global Capital, the hedge fund that bought the Tribune in May, 2021, quickly and selectively cut costs, a common move in a time of tanking newspaper circulation and sanitized political perspective.

Remember the “want ads”? Newspapers’ late-20th century circulation disaster is most associated with dinner-hour TV news and creeping semi-literacy, but a major contributing factor was the internet’s death blow to newspapers’ cash cow of want ads. That loss might have seemed penny-ante, but it wasn’t.

Within a month of Chicago’s new hedge fund journalism era, the new owners sanitized the Tribune of its two prominent conservatives, first Kass, then outstanding Editorial Page Editor and writer Kristin McQueary. Why was Kass, with his large audience and national reputation, so quickly sent packing?

The job was rushed by reliable tools of the left: a politically orthodox labor union and a concocted smear. The Tribune Guild screamed the slander that Kass’ criticism of Soros’ pro-criminal investments was nothing but antisemitism — because Soros was Jewish.

Kass’ columns said absolutely nothing about Soros’ ethnicity or religion, and used no anti-Semitic “tropes,” as the union thugs alleged. The charge of anti-Semitism was not simply false, it was a strategic lie, like the charges that any opposition to an Obama policy was motivated by racism.

You’re excused if you skimmed through the previous paragraphs. Revisiting an old, preposterous lie is wearisome. But then, some ideologues still believe the heavily reported, Pulitzer Prize-winning fiction that Trump collusion with Russian operatives won him the 2016 election.

The Guild’s smear was obvious and easily disproved, but in less than a year it served its purpose.

Consider Kass’ experience in 2020 and later by imagining how you (especially you trolls) might have handled the malicious attacks showered on him. Have you ever been harassed by falsehoods promoted by co-workers? What if they published “exposes” of a home you’d moved your family to because the city you fled was turning into a haven for repeat criminals?

Consider whether local violence and expensively dysfunctional government could be a factor.

Dare to recall mayor “my d*** is bigger than yours” (who next became a Senior Leadership Fellow at Harvard ). How about successor mayor “it is not constructive to demonize” (young rioters)? He’s still on the job, sort of. Working for CTU, he’d done Chicago the service of organizing disastrous teachers strikes in 2012 and 2019. His current incompetence as a mayor probably looks less disturbing from across a state border.

Removed from his audience, Kass immediately moved to reconnect with it by establishing a website. Not an easy enterprise, but he succeeded at it. As Chicago continued becoming more impaired by crime and debt, Kass’ columns became a more irreplaceable resource. Readers again had commentary not restricted by left-leaning corporate media.

Then 18 months later, new challenges: a heart attack, quadruple bypass surgery, a series of strokes, tough time recovering in strange beds, and a pasta ban. But with courage as a family resource, Kass survived.

He gets around with a cane now. Yet he still writes columns that nobody else can write. Guest columnists contribute to his site, but since nobody else has his Chicago experience and history-inflected voice, that’s a challenging contribution, believe me.

I’d guess he might be uncomfortable with this column, viewing hero nominations with skepticism, never recognizing a hero in the mirror. Maybe a certain Sicilian will persuade him to run it.

Though I feel like I know him from his work over 29 years, I’ve still never met him face-to-face. We are two opposite-pole ex-Chicagoans.

My old home city, now plagued by scary-clown mayors and revolving-door jails, has my best wishes from behind the Cheese Curtain. It probably has the same from the writer who carries on gamely in the greater Hammond area, the possible new NFL site. (Which is worse: Bears management or Illinois government?)

This white-bread suburbanite spent a few years in declining Chicago, then moved to uncomfortably ascending Packersland (while still subscribing for years to the Tribune). A Chicago refugee like Kass, I can imagine finally meeting him. Maybe we could find a neighborhood bar on the West Side, raise two small glasses of Greek beer and enjoy just a few ounces of braised lamb.

A meeting would be nice but isn’t necessary. I know him. So do you.

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Bittinger is a non-distinguished graduate of Glenbard West High School. (You should see its wall of Distinguished Alumni Awards).

He’s also a graduate of Vassar College’s first coed class, and as a devoted admirer of Mahler, still finds his brilliant, complex symphonies easier to understand than brilliant, complex women.