Chicago’s Main Event: The Race for Mayor

By John Kass

January 1, 2023

Some still think of Chicago politics as prizefight, with the winner grabbing the government hammer to beat opponents into submission with “the rule of law” and take the spoils the Chicago Way.

And now the holidays have passed, the main event, the race for mayor of Chicago, is about to begin in full this week.

The lead candidates are well known, businessman Willie Wilson, incumbent Lori Lightfoot, former Chicago Public Schools chief Paul Vallas, U.S. Rep. Jesus “Chuy” Garcia, Cook County Commissioner Brandon Johnson and 6th Ward Ald. Roderick Sawyer, son of the late Mayor Sawyer.

And the issues? If you know anything about Chicago, you know there are four critically important issues:

Crime, crime, crime, and crime.

Ask yourself: Which candidate has the capacity to manage a thoroughly broken city and repair the damaged police department?

And which candidates will just run their mouths and play the race card?

Each candidate has vulnerabilities, weaknesses. For example, Paul Vallas is white and loves the city. But he’s terrible at sound bites. His sons are first responders, one a cop, the other a firefighter. His wife Sharon is a former police officer. All this in the eyes of some is a sin.

Democratic socialist Chuy Garcia, also cares about the city. The socialists seem to be gathering momentum in Chicago. Yet Chuy was a surrogate for the defund-the-police left, and for Sen. Bernie Sanders. In a city plagued by crime, will Chuy’s opponents use that against him and risk alienating the Latino vote? And what of his Chuy’s association with the indicted fraudster Sam Bankman-Fried, the bankrupt crypto currency hedge fund FTX?

All of it is fair game. But how the candidates play it depends on how each campaign believes it can play the media.

The candidates will criticize each other, attack and snipe at each other. Things will get rough. If you don’t like pushy talk, if you don’t relish argument, then you probably don’t like politics. Mr. Dooley, the legendary Chicago tavern-keeper insisted that politics ain’t beanbag. So, if you’d rather sit on the grass in the sun, and talk of hugs, kittens and unicorns, think of Mr. Dooley and please go and just enjoy yourself.

But you can’t help Chicago that way.  Pay attention. A great city is dying.

It is being killed by violence and a political class that sees benefit in a terrible bargain: they’d rather virtue signal about “mass incarceration,” than protect the virtuous by segregating the violent from the decent. They buy votes with Chicago’s death.

“Over the holidays, everyone was talking about crime,” said a man who loves Chicago and has been close to mayoral politics for decades. “What do people talk about? It’s all about crime. Where do you go to avoid it, how not to go to dinner downtown? How Michigan Avenue is a ghost-town. If the city’s not safe–and it’s definitely not safe now–then the city can’t come back. And every day Chicago loses more and more people.”

So as the mayoral race begins in earnest. In the city of tribes, the tribes gather. And how you see them depends on where you sit.

You might see them as the Visigoths running down that seventh hill to the city, or as the government (public) employee unions dominated by the white lefties. You might see them as street gangs activated as in the old days, or as legitimate social justice warriors committed to ending cash bail and reducing the reach of law enforcement.

You might see them as small business owners trembling and fearful at those political forces that keep whispering, “Get the bleep out.”

You might see them as good people of every color and creed doing what Chicagoans have always done, trying to stand up after being knocked down hard, because they had the will to stand and do what had to be done.

They’re out there. And they’re waiting for the campaign, these tribes. They tromp through wet cinder alleys, torchlight falling on the heads and shoulders of excited men and boys shouting to one another, on gaslit streets as they’re funneled toward the amphitheater to witness the great brawl between the champions, with the winner grabbing the spoils.

Years ago, it was an all-ethnic affair. The Irish here, the Italians there, Lithuanians, Germans, Blacks, Poles, Latinos and Jews, a smattering of Greeks, Croatians, Serbs and Bohemians (and apologies to any I’ve forgotten), and all cheering their gladiator avatars for control of government under the old Chicago Democratic Machine.

There was some merit to it. If you were better at politics than the other guy, if you were more devious, you got to reap the rewards. I suppose you might say it was a vulgar time, but I was there. And I’ve been called vulgar.  But there was a truth about politics then.

The corruption was only about the money. It didn’t take your soul.

The left hated that old spoils system, and the newspapers especially hated patronage. The good government types that love to lecture others and virtue signal over public television, like that station Winnetka Talking to Wilmette, also loathed patronage.

Patronage was a stench in their delicate nostrils, because it had nothing to do with qualifications or merit.

But now the Democrats are all about “equity,” which is government using skin pigment to reward some at the expense of others and buy political support from the beneficiaries. It is nothing but racist political patronage. They use it to buy votes and pound even more equity into, or out of, the taxpayers.

There have been thousands of shooting, again this year, and more than 700 people murdered in Chicago according to reports. Again. Yet some in media see a miniscule drop in murders and shootings from last year and promote that slight drop as if seeking to be fed sweetmeats from the hand of the mayor herself.

But overall, the ruling Democrat approach to violent crime in Cook County and statewide–endorsed by the incumbent mayor, governor, county prosecutor, county chief judge, state attorney general and Cook County board president–is to offer mercy to the violent.

And, to avoid incarcerating these thugs in exchange for votes.

Most of the victims of violent crime in Chicago are themselves minorities. And few lead Democrats in Chicago politics actually weep for their pain, or condemn this cynical bargain between politics and the habitually violent lest they themselves be called racists. If they condemned it they’d be hypocrites. Because they’re in on it.

This how you kill a great city.

I write this column late on New Years’ Eve, as the State Supreme Court has finally weighed on the controversial “Safe-T Act,” the radical Democrat push to end cash bail in Illinois. It would be a state-wide expansion of Democrat Cook County crime policy that has devastated the metropolitan area with 40 percent increases in crime.

But at the last minute, the high court voted to continue using the old cash bail system for alleged violent criminal offenders.

Cook County Democrats, led by Cook County Board President Toni Preckwinkle, her protégé Cook County State’s Attorney Kim Foxx and the Black Legislative Caucus have tried to end cash bail with the help of Democrat Gov. J.B. Pritzker and Illinois Attorney General Kwame Raoul.

Will Preckwinkle’s no-cash bail policy–appealing for votes at a painful cost–become part of the mayoral campaign debate? Of course, it should, but will it? Lightfoot endorsed Foxx to curry favor with Preckwinkle. Why did she do it? She trashed Boss Toni in the last mayoral campaign. You might think Lightfoot wouldn’t need to grovel. But she did.

So you might suppose media would make an issue of the Illinois Supreme Court move, in the context of the mayoral campaign. You might think it might have something to do with whether the city will survive or if it will devour itself in some dystopian frenzy.

Am I being impolite?  I suppose so. Don’t ask me. Ask some milquetoast local news exec who loves “speaking truth to power.”

The stories of Chicago crime run together, anecdotes colliding in a never-ending orgy of violence. Some just give up on the news. But others who want real crime coverage don’t read the papers. They go to the CWB Chicago website.

The elderly woman walking her dog Jasper was robbed at gunpoint. The city shrugs. That young man, the cook, shot for his cellphone in Lincoln Park. The city shrugs. A gunfight in a downtown parking lot? The city shrugs. The old man beaten. The woman thrown on the train tracks. Those looters in the Loop. Official Chicago shrugs. But the city dies.

The mayhem on CTA rapid transit continues. That woman in Lakeview is attacked, pulled down by thugs. Her scream is recorded on a doorbell camera. That scream, featured in a political commercial was a desperate appeal for law and order, a rallying cry for the decent against the indecent, a woman screaming for help.

But it didn’t become a rallying cry. Because those who dared mention “the scream” were condemned as racists by the Democrat governor and mayor, and vilified as racist extremists by establishment corporate media. This is Chicago now.

That brutish story of the Chicago mayoral campaign as a prizefight could have been told in some movie, a new one with hand-held cameras catching fight fans running through the alleys toward the ring to the Dropkick Murphys “I’m Shipping Up to Boston”

Or in an old in black-and-white film, the fighters staring, judges at ringside, harsh light, and the editors and publishers of old-timey metropolitan dailies in suspenders and fedoras, with spines of steel to chronicle the events as the city waited to see the new boss.

But there are no such dailies. Nostalgia is poison and dangerous, and like questionable street food best to be avoided lest you end up in the gutter. Nostalgia is deadly for writers and troubled cities.

“A prize-fight is simply brutal and degrading,” wrote President Theodore Roosevelt, a true political reformer, enemy of corrupt big city machine politics and amateur boxer who loathed prizefighting in an article in the North American Review in 1890. “The people who attend it, and make a hero of the prize-fighter, are–excepting boys who go for fun and don’t know any better–to a very great extent, men who hover on the borderline of criminality. And those who are not are speedily brutalized and are never rendered more manly. They form as ignoble a body as do the kindred frequenters of rat-pit and cockpit.”

You might not think George Bellows’ painting of the 1923 Dempsey Firpo fight works to illustrate Chicago mayoral politics. Yes Dempsey was knocked out of the ring, he was loopy, but he got back up to mercilessly beat Firpo, knocking him down seven times in two rounds. But that’s a Hollywood ending.

The Norwegian painter Edvard Munch wasn’t Hollywood. His painting formally has nothing to do with Chicago, though it was completed around the time my grandfathers came here, hard-bitten mountain immigrants, with no education but plenty of guts.

They were poor, desperate and hungry men like those Visigoths with families depending on them, not looking for a city of God exactly, just hoping to find a few streets paved with gold.

Munch’s painting does speak to modern Chicago, today’s city of rising crime and the mayoral campaign, and the political class stepping over minority victims of violence, the politicos working to abolish cash bail for violent offenders.

And with a media ambivalent, in a city where public schools don’t teach kids to read at grade level, a city of small business owners trembling, waiting for the next wave of looters, with CEOS of large corporations waiting for the next shootout in some downtown parking lot, taxpayers voting with their feet.

Munch very much understands today’s city by the lake. Just look at the man in the painting. You can see him scream, like a Chicago taxpayer.


(Copyright 2023 John Kass)



Edvard Munch, The Scream, pastel, 1895


(Copyright 2023 John Kass)

Comments 61

  1. The Democrats are the party of the monied interests just like the Republicans are. There is little difference. They cater to elites, donors, and corporations. They influence peddle, insider trade, shakedown rich and poor alike, while posturing about “caring”. It’s all a grift.

    They hide behind a relative handful of elite black, gay, trans, while using race, gender, sexuality, class as a cudgel to keep us divided.

    They could not beat a mope like Donald Trump on the square, with policies that 60% of the voters would like, so they use the race card, the justice system, and a compliant media to attack him. Imagine losing an election to sn idiot like Trump. Clinton must have been so embarrassed. It serves her right as she’s never really had to work for a living.

    The media has done such a good job demonizing Republicans and carrying water for a just as corrupt Democratic Party that half the public thinks they actually care about their well being.

    When I see all the money they’ve wasted, it makes me sick. Think of all the infrastructure they could repair, public hospitals, clinics, first class schools, broadband, and public safety we could have had.

    They make me sick.

    1. They make you sick? What have you done to alter the scenario? Have you run for office? Have you contributed to a candidate? Have you gone to board meetings, school board meetings or other public forums? I think you are a complainer and nothing more. Your descriptions of President Trump, mope and idiot is something you see when you look in the mirror.

      1. Yup, mope. Your sophomoric, ham handed insults show a lack of judgement and discernment. However I cannot really be upset at anyone who voted for Dumb Donald the first time. Look who the alternative was. And Biden is not much better, but Honest, tax paying, philanthropic Trump sure does bring the hate, doesn’t he? We who dislike him and boot lickers like you. How can we honestly defend any of them I ask.

        1. You never answered my question. What have you ever done to improve the situation? All you do is throw insults and demean people. Comparing Biden, your hero, to the accomplishments to President Trump is easy. Biden is helping Lightfoot, and the rest of the Progressives ruin this country. Trump tried to change the course created by Obama and his lackey, Biden.
          I have sat as an elected Trustee in my home town, the same town John Kass was resided in. I have done my part, what have you done?

  2. Perfect analogy!! Equity is the new clout, bound by nepotism. It has, as in the past, lowered expectations and drive. The hypocrisy is astounding!
    They revel in their divisiveness, “Keep at each others’ throats and they’ll never turn on you!”

  3. Chicago is done. Virtue-signaling is now all that matters to those in power. How can a city survive when that is the motivation of the politicians?
    Lightfoot put most of the nails in the coffin. She shouldn’t even be part of the discussion, and wouldn’t be but for the virtue-signalers
    Vallas could possibly turn it around, but like you pointed out, his strengths are exactly what will keep him out. He cares too much about the city, and that is unfortunately what will disqualify him in the chumbalone mind.
    No, Chicago is done. Walk away and don’t look back. It’s not worth it.

    1. Paul’s not ready to walk away. I think he can win. There is a path. but can anybody turn this broken hulk of a city around? I don’t know. Hope so, for memory’s sake.

      1. Yes, he could as long as he gets the right “power” and “message” and image. Gonna be a long road but if he gets the right people to help him run….it’s possible (in my opinion)

  4. It’s tragic to see what has become of my once-adopted home town. I relocated to Chicago for work, and in the nearly thirty years I lived there, I was proud to call it home, except for the last five or six before I fled to Texas.

    Sadly, what’s happening now was as predictable as the Cubs being out of the pennant race by the end of June (before the 2016 anomaly of the Theo Epstein era).

    Single-party (in Illinois, that party is known as The Combine) rule eventually gives way to tyrants, especially when the fourth estate abdicates its role as an unofficial and independent check on institutional power, and willingly becomes the official mouthpiece of the tyrant occupying the given “elected” executive or legislative office.

    It’s what gave Illinois, Mike Madigan, and it’s what gave Chicago, Richie Daley, then Rahm Emanuel, and now Lori Lightfoot. To be balanced, a “Republican” would have been no better – the Republican Party in Illinois, and Chicago especially, is a myth – it is merely the other side of the Combine coin.

    There is much Chicago had that Texas does not, and I miss a lot of it – but no state income tax (and a constitutional amendment prohibiting its imposition) and affordable property taxes goes a long way to compensate for that loss. What I loved about my adopted city has been gone for a long time, now, anyway.

  5. Equity is nothing more than giving the advantage to minorities. No longer content with being “equal”, liberal equity activists are as vigorous for their 1% just as they are so militantly opposed to the richest 1%.
    Unfortunately, Chicago has extended the reach of their violence to the rest of Illinois. It’s not innocuous and it not subtle. We are seeing the same brazen, careless disregard for both victim and innocent bystanders 250 miles away from bloody Chicago.
    There is a prison 15 miles from me in a city of 30,000 people. There is Chicago-style crime there-guns, drugs, robberies, shootings. Sound familiar?
    Prisons are supposed to incarcerate and rehabilitate the criminals.
    Instead, they are a magnet for relatives and friends who infiltrate the community with gang members and girlfriends. And they are not holding prayer vigils outside of the prison.
    Safe-T-Act is supposed to inject “equity” into the criminal justice system?
    I submit that it only criminalizes law-abiding citizens who dare to defend themselves against anyone foolish enough to believe that they can commit a crime and to get away with it.
    Guns-especially illegal ones re-tooled to fire fully automatic-are status to the “disadvantaged”. Given the choice between a gun and a Micky Mantle rookie card, they will take the gun every time…
    And then rob you of the baseball card.
    See how that works?

      1. I am flattered by your comment.
        Strangely, I used to write blogs for fire service webpages. I wrote under the pseudonym Chief Reason.
        I have always believed in “the beginning, middle and end”.
        I’m a nut for grammar and spelling.
        I love your writing.
        It reminds me that writers can paint as vivid a picture with words just as the artist uses paint.
        In the end, you either have something that is beautiful or something that is grotesque.
        Either way, it’s still “art”.

  6. Excellent column, as always!
    But there is the rub: at what point will enough be enough for the citizen/taxpayer? What will be the actions of the citizen/taxpayer? Will it be a Bastille revolt?

    1. those of us who would have manned the barricades are no longer there. i stopped at a gun shop in the new hood, and I asked “What are the rules?” The guy behind the counter said, “I recognize you Mr. Kass! What are the rules? The rules are that you lived in a communist land. You left. And now you’re in Indiana, part of the United States of America!”

  7. John you correctly described the Democratic machine of Chicago through the 19th and 20th centuries although you left out the Germans.
    Patronage was the coin of the realm and Ward bosses were awarded according to their ability to deliver the vote. The voters expected the bosses to keep them safe and protected from crime if they failed they were replaced. It had little or nothing to do with race. Black as well as White ward bosses understood this.
    Police commanders understood this as well.
    Today Chicago and other big cities are ungovernable because our leaders are no longer leaders.

    1. I forgot the Germans. Sorry.
      And you make an excellent point, better than my clumsy attempts. You write “Patronage was the coin of the realm and Ward bosses were awarded according to their ability to deliver the vote. The voters expected the bosses to keep them safe and protected from crime if they failed they were replaced. It had little or nothing to do with race. Black as well as White ward bosses understood this.
      Police commanders understood this as well.”
      You ever want to write a guest column, let me know?

  8. Bingo!!! “But now the Democrats are all about “equity,” which is government using skin pigment to reward some at the expense of others and buy political support from the beneficiaries. It is nothing but racist political patronage. They use it to buy votes and pound even more equity into, or out of, the taxpayers.”

  9. Most likely, this will go the way of the midterms, ie. nothing is really likely to change. So many people in so many ways in so many places had a chance to make a statement and like a Bear running back of the 70s plum fumbled the ball. Lightfoot needs to go, yet is Chuy or Willie (Wilson) really any better ? Quite frankly, I don’t think so. Vallas is a pipe dream. The most obvious yet the least likely. And, if something “good” were to evolve out of this election, the good voters of Illinois stuck us with Toni, Kwame and JB. Again, a chance to send a message, but when push came to shove, crickets. It certainly didn’t help that there wasn’t a half decent candidate to truly compete. First chance, I’ll be gone, done with this hell hole of a state, just like many others. Frankly, I can’t wait.

    1. Ken, I don’t think Vallas is a pipe dream. I don’t think he’s Jesus with miracles. but if he’s not elected, the city keeps circling the drain. in my opinion.

  10. “The corruption (back then) was only about the money. It didn’t take your soul.” – John, this line sums it up in two sentences! I pray Paul Vallas wins. I know he’s been working hard. I saw it first hand when I was on banner patrol for Darren Bailey at the Bud Billiken parade in August! 🙏

  11. Γιάννη,
    I doubt that any of these candidates can rescue Chicago. Only one with the brains and a plan is Vallas, but the Chicago Way is against him. I fear just another socialist hack will assume the role as mayor, and preside over the last rights of a once great city…see LA, Portland, SanFran, NYC and on and on. God help us all 🙏

    1. hey cousin leo, besides paul they’re all malakiesmeni. lori especially. she knew kim foxx was the wrong signal for chicago. it was City Hall’s message to sentintent beings to “get the bleep out now.” she knew it was weak to endorse kimmy, and still she did it, because she has no judgement. as to vallas, there are many “establishment types” who aren’t ready to run, and might want to see a chuy and then they clean up years later after the chuy socialism train rolls off the rails. but by that time, chicago will be all but dead. does chicago really want that?

      1. John, about the only thing worse than watching the Bears play yet another miserable game is watching the Packers work on backing into the playoffs by humiliating the Vikings.

        If Chicagoans can throw out Madam Mayor (and I give that better than 50-50 odds), maybe they can get rid of the McCaskeys as well.

  12. Chicago is dying but the politicians, news reporters and special interest groups won’t admit it.

    Both my wife and I were born and raised in Chicago and lived here until we spent twenty years in he Detroit metro area and had a chance to move back to the western suburbs in the late 90’s and found “you can’t go home again”. We used to visit Chicago restaurants, shop Downtown, go to Bear games and take nieces and nephews to the Museums – but no more. During the summer, we’re fortunate to spend some time at our cottage in Indiana but there is no way we’ll take the Eisenhower and Dan Ryan to get there even though it adds a half hour taking the Tri-State.

    Several years ago, our daughter got a job living overseas. I am so, so glad for her safety since she was able to rent her Lakeview condo and doesn’t have the exposure to the daily violence and crime that living in that neighborhood entails. She spent five years in a Middle Eastern country which I visited several times and felt she’s safer walking unpaved streets as an American there than walking to Lincoln Avenue for groceries in Chicago. Even though she’s losing money on the rental, she can’t sell due to the drop in property values caused by the exodus of residents to the suburbs.

    As for us, we’d leave this state in a heartbeat but, unfortunately given our ages, the thought of moving to Indiana or Michigan is daunting. Oh, well, life goes on —

    1. well if you move here we can sit out on the deck in the late afternoon, drinking highballs and not worrying about getting shot. it’s amazing, yes i know.

  13. We recently retired and spend the winters in Mesa AZ. Fortunately our summer place is in a NW Suburbs private campground so I no longer chained to rising property taxes and plummeting home values. But I digress. I do gig deliveries for fun money and often wear my White Sox gear that prompts the conversation. Usually the first words out of their mouth is “What’s wrong with that looney mayor of your?”.

  14. Thank you John. And thanks to a bunch of the commenters. I haven’t left the city, yet. The last 6 years have been terrible for every law abiding citizen, throughout the country, not just here. What can citizens do? Know your neighborhood. Don’t be afraid to demand change. Go to the beat meetings and meet the officers working your block. And spay attention to your surroundings. Don’t be afraid, but be aware.
    Happy new year all, and go bears.

  15. John, Happy New Year. Hope your shoulders are good. I just had a knee replacement 3 days ago,and think about you while rehabbing, and thinking about your roasted goat! YUM!!
    Anyway, the Dems sucked in the people by whining and sniveling about losing Abortion right here in Illinois, while touting the law the Commodous Maximus had passed to protect it, and the DEMS in Crook, Chicago, and the rest of Illinois freaked out, and voted the Plantation Overseers back into office.

    Toni Prikwinkie got what she wanted by keeping thugs out of jail and saving money, while Barney (Dart) Fife can run around with the Old Roscoe (of which he doesn’t even know what his Deputies carry) with one bullet in their pocket to protect themselves.
    The assault weapons ban in Illinois is a joke. The city killings don’t affect people but hit a BIG MONEY TOWN like HP, and OMG, what has been going on here? Too many balls about existing laws were dropped there by local and State Police (as seen on the guilty look on the SP Directors’ face)which everyone conveniently overlooked, especially the OWNED MEDIA. The media is gutless in this Chicagoland area, and everywhere else for that matter. I watch the nightly news to see how they market it for everyone to believe it, and sadly they do.
    Keep up the GREAT work John. You are the bright light.

    1. thanks Lawrence. You keep subscribing, i’ll keep writing. corporate media has really let chicago down. except for fran spielman ST, mariane ahern 5 and craig wall 7, do the others know how to cover politics? or is it that they’re just bleeping lazy, or frightened to anger some of the karens?.

  16. Happy New Year John to your family and your print family as well! GET and STAY healthy this year we need you!! I get angry and sooo frustrated that i need your words to help keep me in line. There is no way you would ever ask me to write an article for you!! Good Luck to all in the coming year

        1. As a union electrician, surely you’ve seen things in politics that were more shocking than what you dealt with on the job.

          Back when we lived in Rogers Park, in the early 70’s, you could walk the streets safely all the way to the Loyola campus, something my wife and I would do on a pleasant Saturday evening. I’m not sure it would be safe to walk to the El station now, much less ride it.

          And every time the garbage truck showed up to collect the trash at our apartment building, the super was there to slip the driver a twenty. That’s how Chicago worked back then.

  17. I had a nightmare about Chicago the other night. I wrote about it. I still don’t know why it disturbs my rest. I don’t live there anymore. I only lived there for 65 years. But those who are unable to flee still haunt me. The sadness steals my sleep. They need prayer. I have said mine for them. The prayer list gets longer each day. And the poor people always need the most because they are the least able to get out of the way. Great column John.

    1. Hey Grant Davies, I saw your piece on nightmares. You ever going to submit a piece to johnkassnews? going under the knife soon. I’ll be throwing sliders by opening day, but it might take me a few days to get up to speed.

  18. John,
    I agree, Vallas would be the best, but could he govern? Remember Rauner could not get anything done due to Madigan etc.
    Washington had similar problems.
    Perhaps that would be best. Just sayin’.

    1. yeah he could govern. chuy could govern, lori can govern, johnson can govern. what kind of government do you want? that’s the question. fix the cpd and push real school choice pronto or Chicago won’t recover. it’ll become a sinkhole and drag all of the county in. by then Boss Toni and Pritzker will be gone, after having their butts kissed by media.

  19. Thanks for the good an important column that needed to be written but I hope you give us an occasional light-hearted column to lift us up in these depressing times.

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