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 4th 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/
Subscriptions available.
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.
-30-
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.
Merchandise Now Available: If you’re looking for a gift for that hard-to-buy for special someone who has everything, just click on the link to the johnkassnews.com store.
Where else would you find a No Chumbolone™ cap or a Chicago Way™ coffee cup?
Because I know this about you: You’re not a Chumbolone.
Comments 25
Oh yes. She is the boss alright. They win Elections as soon as they get the 15 days to count absentee ballots and count dead bodies and choose the ones they want. Wake up people. Now you will pay the price by high Pensions for them. Ridiculous that folks are asleep. Wait until your new tax bill comes. John thank you for always telling the truth.
John writes passionately and wisely on this and other subjects relating to local politics. Ive stopped caring because the Chicago and Illinois voters keep electing the same people and supporting the same policies. That’s their choice. Complaining about it just isn’t interesting.
Boss Toni, the dull and humorless Foucaultian autocrat, will nod to her Yeoman Cavalry ( Tommy Dart or some other pale retainer) and undo young master Brandan, just as she did with Paul Vallas. A Joe Trippi, or one of his oily ilk, will cause Alderman Reilly to self-destruct.
Remember Preckwinkle owns a cohort of pale yeoman ( 19th Wardand others) with good County Jobs and swell pensions ready willing and able to again do Toni a solid.
https://johnkassnews.com/joe-trippi-should-wear-the-jacket/
On the money!
Speaking of corrupt odious ilk, “Ricky don’t call that number” (1-202-225-5701)of the rancorous local Representative the “Honorable?” Delia T. Ramirez who is an anchor baby, was born to two illegal aliens from Guatemala, married to a DACA enrollee, and has the audacity to claim, “I am a proud Guatemalan first before I am an American.” Like her Somalian counterparts in Minnesota. she should be deported the the foreign countries to which they all pledge their allegiances.
What do you suggest we do with all those who voted for her? I agree she should be booted out of Congress and the country if she feels she is not an American, but what about the idiots that put her in office? Even she is not booted out, at least remove her salary, pension, and the other perks she now enjoys at our expense.
Until the last 20 years or so the
“Melting pot”analogy to US Immigration was still alive. People stood in line to come to our shores and gain the American Dream. They had already invested time in the idea to become “Americans” now we have doors flung open by Biden there is no appreciation by the immigrants and there are massive handouts, nice hotels and warm meals. The worst of the illegals end up on Alligator Alcatraz with three hots and a cot and the liberals (and inmates ) wail about cruelty. Even AA is better than they had at home unless they were some drug lord.
Proclaiming they are a proud (name your country of choice) over a proud AMERICAN says it all. Send them home. As far as office holders they must be American born period. We have to somehow turn the heat on the melting pot so the immigrants will blend in.
Bravo! Well said.
Ramirez embodies why we need to stop “anchor babies”. Another Communista getting wealthy on the public teat. Trump is absolutely correct in taking this to the Supreme Court but needs to make it a constitutional amendment. I went over the fence six years ago and escaped to the Free State of Texas. Amazing how the media has formulated some type of “national crises” over the Texas Democrats fleeing to the worst gerrymandered state in the union. Illinois. Trust me, NO ONE HERE CARES. NO ONE. No demonstrations. No riots. Nothing. Illinois is a ” Sanctuary State” and is welcome to keep them. PLEASE. AND IF YOU TAKE BETO O’ROURKE TOO WE’LL TOSS IN A FARM PROSPECT AND A PITCHER TO BE ANNOUNCED AT A LATER DATE.
Agreed!
Brendan Reilly had better hire protection and keep looking over his shoulder.
It’s the Chicago Way! So sad! Keep writing John; maybe, just maybe the ‘folks’ will
wake up before Chicago goes completely under.
Do you think Boss Tony and Pompous JB will try to keep these Morons from Texas in the state so they can vote for all of our far left wing communist elected democrats? If you have ever watched videos of Hermann Goring, Hitlers Air Marshall, he is always walked around with some kind of ceremonial scepter. Whenever I see Al Green, the idiot congressman of Texas and that gold handled cane, I can only think of Goring and the damage he did to humanity. Green and the democrats adore Goring and his ideology and are doing the same thing to America.
Like Stalin, she counts the votes. If she were able to mass the same government power Stalin had, do you think she’d be any different?
Illinois should be an economic juggernaut. We sit at the crossroads of the air, rail, and interstate road system. We sit on of the largest bodies of fresh water in the world. We have enormously fertile lane. We are home to world class universities and hospitals. We are a major financial center. And yet the city, state, and Cook County are financial zombies. How does this happen? How do Dems wake up on election day and say I want more of this? Where is the Republican party?
So Toni Preckwinkle is Cook County Board President, Stacy Gates is Chicago Teachers Union President, and apparently Chicago is now getting by without a mayor. Well, this is Detroit West. Keep your head down.
So what’s Chicago’s third most impressive post-Lightfoot embarrassment? Non-demonization of flash mobs? The Bulls’ $90 million extension for Patrick Williams? The Tribune Guild?
Whoever the CTU supports will win.
You are correct. And when the CTU backs Brandon Johnson again, doesn’t Brandon win? I know the low favorability ratings for BJ sound dire; but by election time the CTU and its puppet BJ will spin it all for the supplicant reporters, demonizing others and saying BJ needs more time to undo decades of whatever (“outside force Tier II makes it worse,” “greedy millionaires make it worse,” “historical injustice X is unfair,” “the mayor is working really hard for working Chicagoans against all those forces of evil”). It pains me, but it seems like Brandon could totally be re-elected.
Hey, Mayor Sawyer was a decent man and certainly NOT a traitor. It was Tiny Tim, the traitor who helped to split the black community votes in the primary to favor the election of Daly II and to be rewarded the Cook County Judgeship. Then, I saw Tiny Tim became a Whale of a Tim as a judge when he came, sit next to me in the audience at Mayor Ram Immanuel’s inauguration. I really wanted to punch his big fat belly but didn’t want to go to jail for that!
Brendan Reilly is the ONLY adult in the room at City Council government, and the rest of Chicago government.
Preckwinkle should be beatable given that only ~35% of the voters turn out for these elections. That, in and of itself, is a shameful statistic and the #1 reason we have all this idiotic and corrupt “leadership”. Shame on the voters of Chicago, Cook County, and Illinois. That indifference (laziness?) is irredeemable.
“But she was an alderman, too, once. Now she sits at the center of her web, rubbing her bony fingers together, waiting for prey” – in sensible shoes! There, I fixed it in accordance with prior descriptions of her by you.
I live in the 19th ward. I am down the hill and over the tracks. My neighbors would vote for any Jackson, Johnson or Preckwinkle. The 19th Ward didn’t vote in the numbers they usually vote when Panic ran. Joe trippe sent out a signed letter from the Vallas campaign attacking CPD that wanted to hear DeSantis speak….they heard the message…Vallas hates cops….and many stayed home. Vallas was the only choice and he was destroyed by Trippe who was sent by Preckwinkle to “help”. We get the government we deserve.
Where’s the Moutza?
I found it odd that my Democratic machinist sister, wound up in hock to the grand nephew, Jason Fahy, of the grand wizard of The Back of the Yards, Canaryville and Little Village, Ed Burke himself just in time for ginning the Ukrainian war. (The Fahys are in hot water about Jason’s uncle’s framing of Jackie Wilson, an ongoing case.) Before I had the Madigan mob, who originally lived a borough over from my home neighborhood Chicago Lawn, swarm on me through NU’s freshman year roommate Dan Schaffer’s best bud from draconian Latin Prep, Andrew Madigan in the U Chicago plot to elect Obama; and they needed my help. I find it a little more than coincidental that Madigan’s Worth Township heeled OLPD heavies came and beat my brain in so close to the Vallis-Johnson contest. And then there was Trump (surely connected to johnnies of one side or another), in one of my 8 recovered retrograde amnesiac memories from that time, hectoring the Feds on Twitter as New York’s finest were about to arraign him, with a second uprising coup, this time in New York. My machinist Mom and sister inculcated the Traumatic Brain Injury time warp savior complex well. So I realized as Toni’s paid behavioral forensic psychologist Dr. Noy tried to coerce me into a false confession, that this was a diversionary thing I learned to do when politicos were in trouble, even when I had no skin in the game. Dr. Noy tried to convince me that I wasn’t conditioned to do automatic writing evolving into massive stochastic predictive code, that sirens didn’t torture me to research weaponry for Ukraine or some uncommunicated Manhattan project to if not end the war, stock up on killer science. I refused his BS and my Chicago Machine lawyer, the only we could afford represented by a MAP union family friend, convinced Judge Carrol Howard to get me in a 2-year mental health court. Being in Cook County you realize everything Sheriff Dart and Boss Toni say about mental health treatment there is a sick joke. No therapy, 5 brainless minutes with Dr. Mason, no nurse to ask what meds they were giving me. If I didn’t have a wise roommate I could have been there a lot longer and been shanked by a psychotic rapping roommate or the HIV screamer. None of the things the OLPD said was true and watching the slowly burning brush fire of lies and political persecution (I’m an Independent and investigative journalist as well as techie with tons of knowledge of politicians behaving badly), I couldn’t help but wonder how George W Bush is feeling fine and chipper in Dallas or Crawford, with not a care in the world.
Thanks for talking me out of moving back to Chicago.
If a few years back you would have told me that I would vote for Lightfoot for mayor, I would have known you were insane. When the execrable choice was between her, the spawn of Don King and Beetlejuice, and Boss “Pop Tax” Toni, there was no other option. While both were horrible alternatives, with horrible policies, my thought was that at least Lightfoot would start with a significant power disadvantage compared with Preckwinkle. Didn’t think we could do worse than Lori, but Brandon said “Hold my beer and watch this!!” God help us!