Brendan Reilly, Boss Toni and The Chicago Way

By John Kass

August 6, 2025

If there ever was an Italian artist who would have understood Chicago politics and the Chicago Way it would have been the talented street brawler and killer Michelangelo Mersi, better known as Caravaggio.

His brilliant baroque portrait of Cook County Democratic Party boss Toni Preckwinkle at the top of this column as Medusa is representative of Caravaggio’s struggles against the darkness of his soul. Some historians might object and insist that an Italian painter who dabbled with darkness and light in the 1590s would have little if anything to do with Boss Toni Preckwinkle.

But I point to the Caravaggio portrait of Medusa, the figure of mythology who represents Boss Toni in my mind. It was said that one look from her would turn a man into stone.

Chicago Ald. Brendan Reilly, 42d, is mounting a challenge to Preckwinkle. His petitions of candidacy are circulating as you read this beginning on Aug. 5, he said on the Chicago Way podcast. You can listen to the podcast that I do weekly with WGN producer Jeff Carlin right here.

“I can tell you this, starting on Aug.5, voters throughout Cook County will see candidate petitions on the street for all these offices that are going to be up for election in 2026,” said Reilly on the Chicago Way podcast. “And my name will be on a set of petitions for Cook County Board President.”

Whoa!!

He notes that Democrat educator and budget expert Paul Vallas was badly treated by Chicago voters who elected the paranoid nincompoop and race card expert Mayor Brandon Johnson, he of the panic attacks.  Johnson is unqualified and the whole city knows it. He was a failure as a teacher.

“I run into people who say, what do we do about getting rid of this mayor?” said Reilly. “We can’t survive another month with him and I have to say ‘no,’ we can’t. We don’t have that mechanism. But you’ve got a great opportunity to make a change in the 2027 elections. So, if you’re upset about things you gotta get out and vote. That is the most important thing we can do to save our city and our country in the next two years.”

Preckwinkle, who has done more than any Democrat to destroy Chicago, will finally be held accountable before the voters by a fellow Democrat? She sucked up to George Soros to install the do-nothing Kim Foxx, the lickspittle newspapers protected her and she helped install the hapless Mayor Panic Attacks Mayor Johnson. Now she is finally being challenged? And I never thought that I’d see the day. But that day is here.

Now to be quite clear I don’t see Brendan Reilly as a Perseus to find Medusa of the wriggling hair, staring into the polished shield to avoid her gaze and find her reflection and remove her head. That’s too gruesome.

Reilly, a man of common sense, he would be the first to say that he’s no demigod son of Zeus. He’s a Chicago alderman.

But she was an alderman, too, once. Now she sits at the center of her web, rubbing her bony fingers together, waiting for prey.

I remember her as the alderman of the 4^th Ward, sucking up to the racist forces who sought to destroy a good man, Chicago Mayor Gene Sawyer, a black man that was vilified– I kid you not– as a traitor to his race.  She sang the siren song of progressive (communist) propaganda, hating on Immigration and Customs Enforcement agents so much that she allowed a drunk driver who allegedly dragged a man to death leave the Cook County jail and make his way to hide in Mexico.

She is the George Soros agent in Chicago, backing her witless assistant and patronage hire Kim Foxx, the liar and cheerleader for Jussie Smollett to become the do-nothing Soros prosecutor in Cook County.

She also backed her ally, Chief Cook County Judge Timothy Evans overhaul of the broken bail bond system in Cook County and that further destroyed the broken system. How many Chicagoans have been shot by repeat violent crime offenders released from jail by Boss Toni and Tim?

And she paved the way for another of her witless personal toadies to become mayor of Chicago and drive the city into the ground. She formed the ruling junta that has strangled Chicago.

And yet the soddenly corrupt Chicago corporate media never holds Boss Toni accountable. I tried but the left screamed and screamed about me since I began writing about Soros and his prosecutors. Some Chicago leftists are angry with me still, including a leftist blogger who keeps pathetically demanding that I invite him on the podcast, but I had to leave the Tribune. The newsroom was untenable after I wrote a column Something grows in the big cities run by Democrats: An overwhelming sense of lawlessness. And after I was offered a buyout, I grabbed it and started my own site here:  https://johnkassnews.com/

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Those who remained in the ghetto of Chicago journalism either refused to challenge her policies or were compliant servants of Boss Toni. The compliant media wrung its hands but couldn’t bring themselves to challenge Boss Toni and her furies of violent crime.

The great city of New York—the capitol city of capitalism– has all but capitulated to the far left with the mayoral candidacy of Zoran Mamdani. In Minneapolis Minnesota, there is Omar Fateh, a Democratic Socialist candidate for mayor in Minneapolis, Minnesota.

Paul Vallas would have been a better mayor for Chicago than Mayor Panic Attacks. And now Boss Toni can wear Mayor Panic Attacks on her back and shoulders like jacket for the failed Chicago.

“I can tell you the business community has woken up,” Reilly said on the Chicago Way. “They learned their lesson from the last mayor’s race. They assumed Paul Vallas, because he was supremely qualified and certainly had a much better resume for the job than the current mayor does, and they were convinced that it was in the bag and unfortunately, they took their foot off the gas.”

The “business community” is only part of it.

Barack Obama and his henchman David Axelrod and the rest of the Obama crew could have stood up against Chicago’s racist far left–including Boss Toni–and tried to stop the savaging of Vallas to save Chicago. But they did nothing. They let Brandon Johnson happen.

And Chicago legacy corporate media, the Tribune and Sun Times could have done something, but they sniffed Obama’s smoke signals and did nothing.

Now, the question is for the voters.

Will they do what they’ve done to Paul Vallas and sit on their hands when Reilly challenges Boss Toni, as the spider rubs her fingers in the middle of her web and laughs and laughs?

Or will voters finally hold Boss Toni accountable and save their county and city and vote?

That’s got nothing to do with mythology.

But it has everything to do with the Chicago Way and whether Chicago and Cook County continue sliding down the drain.

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About the author: John Kass spent decades as a political writer and news columnist in Chicago working at a major metropolitan newspaper. He is co-host of The Chicago Way podcast. And he just loves his “No Chumbolone” hat, because johnkassnews.com is a “No Chumbolone” Zone where you can always get a cup of common sense.

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