Chicago’s Incredibly Shrinking Newspaper

July 2, 2025

Buyout offers hint at uncertainty for Tribune reporters

Another Chicago newspaper will be shrinking soon; this time it's the Chicago Tribune. Two weeks ago, Tribune Publishing, which is owned by Alden Global Capital, a hedge fund firm, notified the paper's union, the Chicago Tribune Guild, that buyout offers for Tribune employees were on the table for staffers.

If this sounds familiar, just three months ago, 30 employees, — 20 percent of its workforce — accepted buyouts from the Chicago Sun-Times.

The Tribune Guild is, of course, against the move. “We should focus on building readership by investing in strong coverage,” union vice chair and Tribune reporter Gregory Royal Pratt said on X, “not cutting staff to satisfy short-term greed.”

If only the Tribune's coverage of the news was actually strong.

Background

Founded in 1847, the Chicago Tribune was once a juggernaut. It was the centerpiece of a media empire that included many other newspapers, dozens of television and radio stations, including WGN-TV and WGN Radio, even the Chicago Cubs, which the Tribune Company purchased shortly before going public in 1983. The corporation's growth continued and in 2000, it acquired the Times Mirror Corporation, which included the Los Angeles Times. It was around this time that the Chicago Tribune, once a solidly conservative outlet, began its editorial shift to the left.

In 2014, many of the corporation’s newspapers were spun off to form Tribune Publishing. Alden purchased the scraps, taking the company private in 2021. Since then, few major metropolitan newspapers and a bunch of small community publications remain from the onetime Tribune colossus.

The Tribune is the Chicago media version of Sears. When Kmart acquired the Sears Corporation in 2005, the combined corporation operated 3,500 stores.

Now there are just eight, and none of them are near Chicago. Sears no longer owns the Craftsman and Kenmore brand names, and many non-core retail operations, including Discover Card, Dean Whitter, and Allstate are long gone.

Regarding its eponymous tower, let’s just say it has a different official name now.

As for the Tribune, its landmark Tribune Tower was sold in 2016. Its sprawling printing plant, the Freedom Center, which also hosted the Trib’s newsroom, was demolished last year. Bally’s downtown casino is now being built on that site.

A sham accusation

Shortly after Alden's acquisition of the paper, several dozen journalists accepted buyout offers, including John Kass, the Tribune’s prominent conservative voice who the year prior was unofficially demoted when his column was moved from the coveted Page 2 location to the op-ed section after sham charges of anti-Semitism were lodged by the Chicago Tribune Guild. The union objected to Kass’ criticism of billionaire leftist political donor George Soros. Nowhere in that article did Kass mention that Soros is Jewish. And no “dog whistle” words were used by Kass to describe Soros.

The union lied.

One of the signers of that CTG letter was Gregory Royal Pratt. Clearly, he has an irrational personal grudge against Kass, whose level of popularity when he wrote for the Tribune was at a level Pratt could only dream of for himself. Three years ago, while on the Ben Joravsky Show podcast, Pratt called Kass “a disgrace to our business and our profession” and “an imbecile.”

The second round of Tribune buyouts is here. And there is no reason not to expect a third round as the Tribune continues its downward trajectory.

Traditional newspapers and magazines face enormous competition from a slew of competitors that didn’t exist decades ago when television was blamed, rightly so, for forcing many newspapers, particular evening ones, to fold. The new media of course includes blogs, online videos, and podcasts. However, rather than evolve to survive, most newspapers are now doubling down on their left-wing proclivities.

Even in a deep blue city like Chicago, the far-left is a distinct minority. If the Tribune reached out to everyone else, its situation probably wouldn't be so dire.

Earlier this year, in an essay this author penned for Contrarian, I concluded people are innate gatherers of information. They want to learn and progress intellectually.

A good opportunity to present a balanced view of a controversial story was missed last week by Tribune intern Ikram Mohamed — who certainly has an editor to answer to in her role at the paper. According to her Tribune biography, in addition to holding sociology and journalism degrees, Mohamed has a “certificate in human rights and social justice.”

In her article about the pro-Palestinian encampments at Chicago college campuses, Mohamed interviewed three protesters who support the Palestinian side in the Gaza conflict. She didn’t bother to speak to a pro-Israeli student. The article discusses free speech concerns, but Mohamed should have asked the protesters why they believe setting up a tent city on a college campus is free speech.

My guess is that most people are curious about that.

Well, since the Tribune whiffed on this opportunity, it's up to the Contrarian to set things straight.

According to the Foundation for Individual Rights and Expression (FIRE), the right to utilize an encampment to express free speech is almost non-existent. “The government, including public universities,” FIRE explains, “can still enforce reasonable time, place, and manner restrictions on when, where, and how people protest.”

How hard is it to bring up that crucial point?

Not very hard at all.

But the Tribune's Mohamed chose to side with the entitled and narcissistic protesters.

Real journalism

Getting both sides of the story at a newspaper that purports to be a mainstream media source must be a 20th century thing. Until recently, with most newspapers, such an article would be labeled as “news analysis.” 

A Chicago Contrarian column from 2021 about the Tribune praised Kass, declaring that he “often drew in his audience not because the reader may agree with the underpinnings of his conservative political philosophy, but because Kass took readers into unfamiliar, yet compelling places.”

It's called journalism.

Current Tribune reporters — and those of the Sun-Times and other newspapers — are writing for themselves and to impress their co-workers. The audience, you know, the people who fund the operations, doesn’t seem to matter to them.

They are working in a tough business market that they make worse with their excessive vaingloriousness.

The end is near for the Chicago Tribune. It will be well deserved.

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