Boss Preckwinkle and the New Ruling Junta

By Paul Vallas

February 23, 2024

Mayor Johnson’s road to elective office was paved by the County Board President and Democratic Party Boss, Toni Preckwinkle, and greased with the financial support of Chicago Teacher’s Union (CTU) President Stacy Davis Gates, who literally raised the dues of her members to help finance Johnson’s campaign without approval of her rank and file.

This is their gift: Johnson, a failed teacher turned union organizer, who seems captive of the CTU’s agenda and that of the progressive left. Chicago sees him as its mayor floundering on a number of issues, from the chaos of immigration to street crime.

Stacey Davis-Gates draws much of the attention as it is her style to attack any critics of her or policies as being racist and labels proponents of school choice as fascists, while her union leverages its war chest to successfully lobby against the state’s small scholarship program for underprivileged kids to go to private schools, the “Invest in Kids Act.” This, while she sends her son to a private school, as do almost 40% of her CTU teacher members with school-aged children.

Meanwhile, Boss Preckwinkle maintains an extremely low profile. The goal of the Preckwinkle machine, like that of her predecessoris absolute power and control in which their agendas go unchallenged, dissenting voices are cancelled, and challenges to her decisions are demonized by accusations of racism. In short, Johnson and Preckwinkle’s supporters led by CTU and its network of community-based organizations work to intimidate and silence critics.

In true totalitarian fashion Preckwinkle and her fearful Party apparatchiks squashed a bid for an open party primary and by unanimous consent endorsed Board Preckwinkle’s hand-picked candidate for State’s Attorney, the woefully underqualified Clayton Harris III.

What are Harris achievements in a career of bureaucratic hopscotching?  Leading one of the single most useless governmental bodies in the state, the Illinois Port Authority, and serving as the last Chief of Staff to former Gov. Rod Blagojevich before his was impeached and removed from office.

Why Harris?  Probably the best Preckwinkle could summon in the race to succeed her current protege in that office.  Fealty to the boss is the most important qualification, especially in that office, given Preckwinkle’s determination to continue emptying out the jail. And when the Boss wants to assure there will be no criticism of her hand-picked outgoing failed States Attorney Foxx, who embarrassed the office countless times.

How did Foxx embarrass the office? Cook County residents may have tried to repress bad memories, but who could really forget the Jussie Smollett show?

Foxx handled the Jussie Smollett hate-crime hoax case for which she was investigated and miraculously she kept her law license. The Cook County State’s Attorney’s office was central to the deteriorating relationship with the Chicago Police Department, because Foxx focused more on “racial equity” than on prosecuting career criminals.

That led to an exodus of career prosecutors who wanted no part of an office that didn’t prosecute criminals. Failure to attract replacements leaving the office far short in numbers and experience, effectively limiting both the number and quality of prosecutions.

And what was Foxx’s most significant career achievement prior to becoming State’s Attorney? It was serving as Boss Preckwinkle’s Chief of Staff. She took the orders and “handled” personnel issues. See the pattern?

Meanwhile, Boss Preckwinkle’s radicalized, political machine chose Cook County Water Reclamation District Commissioner, Mariana Spyropoulos, to take on the incumbent and longtime Democratic Party stalwart, the Cook County Circuit Court Clerk, Iris Martinez. Iris began her career 40 years ago in the mailroom of City Hall and is now the highest-ranking Latino official in Cook County. Her offense? Not supporting Preckwinkle’s candidate for Mayor.

There is also her determination to bring full transparency to the criminal justice system so that the public can see the consequences of the county’s early release programs and now the elimination of bail, courtesy of the Safe-T Act.  Spyropoulos has hired Dorothy Brown’s former staff and dumped close to $1.5 million of her own family money into the race. Why? It costs a lot of money to take out a woman of color serving with integrity at the behest of the Boss. Where are the equity police now?

Let’s understand that Preckwinkle is also boss of the judges, including the Chief Judge, Tim Evans, who she continuously browbeats and disrespects. She is the boss of her very own catch-and-release prosecutor, Kim Foxx, who she is now trying to replace with Harris, Kim Foxx’ clone. She is also the boss of the jail and of the decidedly cautious and non-combative Cook County Sheriff, Tom Dart, because she controls his budget and helps him come election time.

And Dart sat back as she literally demolished jail buildings and helped her get the perpetrators of violent crimes out of jail and put onto his electronic monitoring program.  All so they can serve their sentences on their couch, or more likely, commit new violent crimes in our communities on their two “free days” off from being monitored per week thanks to the Safe-T Act.

Let’s fully understand what Cook County Board President has bequeathed us with:

A criminal court system and a state’s attorney who view criminals as victims and who created a revolving door to the justice system, even before the SafeT-Act, the same system that returns three fourths of violent criminals arrested to the street. A county jail that has seen its inmate population cut by more than half the last 10 years despite a 55% increase in major crimes since 2019 alone. And Preckwinkle has bequeathed Chicago with a failed teacher and former CTU lobbyist-made-Mayor, who has embraced a Socialist agenda that is damaging and dividing the city.

Preckwinkle’s State’s Attorney provided further evidence her office has become an advocate for criminals, not victims, showcased in her defense of Assistant State’s Attorney, Michelle Mbekeani, head of the state’s attorney’s Conviction Review Unit. Mbekeani operated a state-licensed business linking inmates with wrongful conviction claims with private attorneys.

This serious conflict of interest and lying when questioned by a judge about it, got her barred from representing clients before members of the Cook County Judiciary.

Her credibility is publicly damaged. But Foxx—protected by Preckwinkle—is allowed to gracefully step away.

Preckwinkle gets a break because the media fails to connect the dots and her low profile, although the media’s failure to call her out for her consistent attacks and the branding of Democratic primary candidates she opposes as racist is also troubling.

She plays the race card and gets away with it.

Recall the lack of reaction when she momentarily dropped her guard and showed her true colors when responding to a question by the Tribune’s editorial board about the pervasive fear of violent crime in Chicago and possible impact of legislation eliminating cash bail?

Preckwinkle made the point that residents in more affluent neighborhoods are now getting a taste of what it has been like to live in the Chicago ZIP codes that have heard gunfire and feared carjackings for years. “She made that observation with a sardonic chuckle,” according to the Tribune. That comment would have made Stacy Davis-Gates envious. The divisive tone would have rivaled Mayor Johnson’s behavior on the Gaza resolution.

Why isn’t Preckwinkle hounded by reporters about rising crime and her policy choices, including Foxx and emptying out the jails? Why isn’t she bothered with questions about children being killed in the street gang wars, or why Foxx isn’t tougher on violent criminals?

Because the media, as gatekeepers allow her to constantly get away with it. And many journalists in Chicago are liberal and share her progressive views. The focus goes to Pritzker, Johnson, Foxx, but Preckwinkle escapes media notice. She never leaves her fingerprints behind.

With so much control and influence over the political machine, criminal justice system, the jail, the judges, and the prosecutor, you’d think media might want to hold Preckwinkle to account. Especially as media wrings its hands and worries about the future of crime-plagued Chicago. But they don’t.

It’s time for voters to do just that—to hold her accountable–beginning with their rejection of Preckwinkle’s hand-picked candidate for the Cook County States Attorneys and the Cook County Circuit Court Clerk.


Paul Vallas formerly ran the public school systems in Chicago, Philadelphia and the Louisiana Recovery School District. He was a candidate for Mayor of Chicago.

Comments 43

  1. And here we are, Paul. Chicago and Cook County is finished.

    I must ask, who foisted Joe Trippi upon you and your campaign? My guess it was Tom Dart, or someone close to him.

    God bless you and Sharon and the lads!

    1. I agree, Pat. That – Trippi consultant – was a disaster. In tennis we call such missteps “unforced errors.” But tennis is only a game. Chicago is not. And we are now all paying dearly for that “unforced error” by Mr. Vallas.

    2. You are not a politician Paul!
      You should have dropped out of the mayoral race and supported Willie Wilson; The only way to counter the race issue. Brandon Johnson would be forgotten and hustling to pay his utilities bills.

  2. Excellent column as usual John, sadly voters are either stupid or apathetic on how their political choices have resulted in ruin to their neighborhoods and their lives. they keep failing to conenct the dots. the media is pathetic in not helping the public to connect the dots. Until the sytemtotally collapses (and it will eventually) nothing much will change. Until the criminals turn on the people causing the chaos, nothing will change. We need a clone of El Salvador president at every Democrat run city, county, state and Federal level. I love how he nicely told the Western Leaders to go f* themselves. the man is brilliant. they would envy his approval rating and his re-election numbers. He got those by succeeding in lowering crime. Less people were killed in El Salvador in 2023 than in Chicago. Chicago should be ashamed. Look at these stats. Chicago population 2.75 million, el salvador population 6.3 million, 2023 murders chicago 568, 2023 murders el salvador 154. El salvador that had a civil war 40 years ago is safer for its residents than Chicago. America should be ashamed. THe democrat party has proven time and again it cannot lead. Yet its leaders get rich while POC die, and they claim racism. Is it racist for black people to kill black people?

    1. It isn’t that voters are “stupid or apathetic”, but that too many are complicit. We lived in Chicagoland for decades before fleeing as refugees and I recall all too often how many “voters” would laugh and express their admiration every time some bureaucrat or politico would push the envelope of corruption. Others just shrugged their shoulders and said, “not my problem”. What we are seeing today is a culture of corruption that has been decades or even a hundred years in the making. As John Kass wrote long ago, Illinois’ state motto should be “where’s mine?”

    2. Due to liberal white guilt despicable African-American politicians, like boss Preckwinkle, can play the race card every time. They even developed a tactic called CRT, whereby a white person is born a racist and nothing can change that condition. What is pathetic is it works. Include her demonstrated racist views, and her actions as the boss and she is clearly a Marxist.

  3. Without a working press there will never be an educated Chicago. Without voices like Kass and Royko people don’t know what’s really happening. There is no alternative voice of any kind. The Trib is unreadable, filled with party line politics and news wire stories. Nothing that would give a reader any insight or even news. Most crime stories are suppressed. The outrage of our failed schools is completely ignored. Once crusading journalists would have been out night and day finding the stories that are killing our city and its people. Telling the truth. It’s the story of a lifetime. White and Black people have this in common: we are all paying the exorbitant taxes that are funding our own destruction. Color is not the issue. Multicolor corruption is.

  4. Well, this is all known, and has been known. What is also known is that the sheep will continue to vote for whomever the media, taking their orders from the progressives, endorses.
    Pointing out the obvious and continuing to complain won’t do a thing. Chicago had a chance to end all this but chose to be led by the liars and thieves.

  5. The elected miscreants who have broken things here have about rendered them beyond any repair. The talent that might have been able to has likely already fled. The last lifeboats are loading now.

  6. Great column from the man who should be leading Illinois but the dems will never let a person with answers win-too bad. Hey John how about having Vince E.Ellison on the Chicago Way podcast. Keep up the great work .

  7. One thing Paul didn’t mention is Preckwinkle’s meddling in Metra. She has already destroyed the Electric District, toying with the schedules and fares. She is behind the silly fare restructure, supposedly reducing them so the hapless and ride for cheap or less. This with the supposed fiscal cliff and sticking it to the loyal riders who left in droves and for many reasons won’t be back. Off track a little, it’s funny, that fiscal cliff…yet Jim Derwinski, another inept figurehead gets an additional $12 grand a year up to like $345,000 or so. I’d do the job for 1/3 of that, and do it 200 times better. Fiscal cliff…ha ! Anyway, back to Toni. She is the one for the drive of giving the RTA more than just fiscal responsibility (which is how the law was written) and combining the 3 service boards into one, most likely (more) inept political structure. How much are her dirty hands into (her?) hand picked people being on the 3 boards, or even positions of authority and power ?

    This is truly one dangerous person, pure and simple. Yet, for some reason, people let her get away with it. Yet, for some reason, she keeps getting re-elected.

  8. It used to be you could look the other way because there was economic opportunity in Chicago. In what industry besides politics can you get rich starting from nothing-and doing it on merit? Entrepreneurship in Chicago is dead. The trading floors are gone. The accounting firms and consulting firms scattered in offices all over the world. The banks are all gone. There are no major big banks left in Chicago and they haven’t been there for a long time. Boeing left. The only industry left is law-the Federal courts are there and they aren’t leaving.

    If you are in your 20s, Chicago is not the place to be.

  9. Ahh Paul, we miss you, and your voice. Besides having been turned into a s–thole city, it is a city of chumbolones, as Yianni as so eloquently put it. Those voters who sat home and allowed Mr.Panix to ascend to mayor are now eating crow and wondering what happened! They only have themselves to blame for spurning your efforts to revitalize the city from the ashes. I fear Chicago is too far gone to come back, unless a miracle of conscience befalls the voters – and the media – to reverse the slide into oblivion. Thank you and Kasso for your stalwart efforts to continue to offer a breath of fresh air into our mundane existence right now! We must all stay strong…εις ανώτερα Paul!!

  10. Vallas makes a tragically accurate accounting of my former home city’s progressive ruination. Chicago could have turned the mayoralty over to experienced, capable Vallas, instead handed it to the teachers union, a grinning goon, and godmother Preckwinkle.

    I’d been thinking that the model of decay for Chicago was Detroit, with Chicago descending toward the state of crime haven and boarded-up buildings that Detroit descended to earlier.

    Now a worse analogue for Chicago’s path occurs: Venezuela. Not that long ago, it had the second-strongest economy in the Western Hemisphere. Then Hugo Chávez and his leftist “justice” tyrants came to power. Venezuela soon became a ruined country where those not in the ruling Socialist elite resorted to eating their pets.

    As Vallas, Kass (and jkn subscribers this morning) have noticed, the price of Chicago’s clueless voters giving a get-out-of-jail-free card to Democrats and associated criminals is high and going higher. If any of those voters are capable of serious reading, they should read up on recent Venezuelan history.

  11. I think may people can agree with progressive goals, at face value at least, like lower crime and keeping neighborhoods together and having kids grow up loving themselves and not turning to violence. What my American Indian buddies and I like to say is – “Why do Indians always say ‘How’ ?”

    Because “How” a person goes about their business is always far more revealing than any business they might be going about – Boss Toni

  12. The clowns and crooks running the state, county and city are without opposition and do whatever they want and the majority of citizens are clueless and don’t care. The Republican party in Illinois is impotent, like eunuchs in a whorehouse. Nothing ill change until we reach bottom, John. And right now we cannot even see the bottom. Keep writing, but you are preaching to the choir and the choir are an impotent minority.

    1. “Democracy” dies when there is no viable alternative to those in power. When and how will the Republican Party regroup and rebuild itself into a strong, viable alternative to the one-party bosses that rune the City, County and State?

      In Chicago and Cook County you have to run as a Democrat. The primary is where the action is.. and where the turn-out is guaranteed to be the lightest, favoring the machine-approved candidate.

      In many City and County elections there isn’t even a Republican running for many of the offices.

      Kass talks about the “Combine” where Republicans joined with Democrats to split the spoils and were finally erased as a viable political alternative to the Democrats. We are now reaping the results of those bygone sell-outs.

  13. Bullies all! As Kasso’s friend from Evanston whose name escapes me at the moment wrote, “reparations by other means” is the perfect descriptor of the situation we find ourselves in here in this Godforsaken state!

  14. Every single voter in Cook County with half a brain or more NEEDS TO VOTE ON MARCH 19th for Eileen O’Neill Burke. And heck even if you have less than half a brain, vote for Burke! Get a yard sign. Spread the word. Even to your Republican friends! Voter turnout is likely to be very low this time, but you know as Paul well laid out, Preckwinkle & Co. will do anything to get their chosen one into office. The last thing we need is Kim Foxx 2.0!

  15. I’ve moved out of the city and county years ago. This ain’t my problem anymore. The voters approve of this degrading of the city, county and state. They get what they voted for. The city is done.

    Look at it this way, the city is in the best shape today because the next day, and following days it’s still all downhill! You’ll look back n 20 years and think today was a good time!!!

  16. Chicago, Cook County and Illinois are done. No longer a matter of if, but when. The Covid bailouts delayed the inevitable, but the path is clear. Paul’s article is terribly depressing, but shows why there is no off ramp to the ride to hell. Voters have a choice, but are left dumb by Chicago’s public education system and the in the bag media. The local media lives here, they see what’s happening, but don’t seem to care. John, you and I escaped to Indiana, but we both left people behind who we worry about. But there’s little we can do now but expose what the politicians and the media are foisting upon the people of Chicago and Illinois. Keep it up.

    1. You are right on. Chicago/Cook County has always been run by a boss – some stronger than others. Preckwinkle may well be the strongest since Richard J. But there is one huge difference between the two. Under Daley I, Chicago and Cook County grew and thrived, and while he was ruthless, he seemed to have the best interests of the city in mind. Unlike Daley, Preckwinkle is a Progressive ideologue, who I’d be willing to bet looks upon fondly to the teachings of Karl Marx. RIP Chicago and Cook County. Illinois is on a banana peel too, but I’ll be optimistic – Michigan survived the collapse of Detroit.

  17. Thank you Paul for this column and thank you John for giving Paul Vallas a podium to talk to Chicagoans about the affairs that force them into a corner. A corner of the sheep pen installed for all Chicagoans by Preckwinkle.
    It would appear to me that she learned her “craft” at the feet of the Daleys. Hmmm. I guess she learned quite a bit. Too bad she has had so many dolts to work with….oh well. Another reason why Chicago is losing business’ and people who are wealthy enough to MOVE away.
    God bless you Paul and John.

  18. The “Critical Theorists” are now running Chicago and Illinois, and most of the big cities and boardrooms of our companies. I fear that we’ve reached the point of no return as the Marcusean long march through our institutions is just about complete.

  19. Chicago no longer has a school system.
    What they have is a minor league organization that is training future Chicago street criminals, while denying school choice for deserving students.
    The CTU has way too much power and should be investigated on RICO charges, but as long as Preckwinkle-an autocrat in her own right-has total control, nothing is going to change.
    Schools will continue to crank out criminals, the states’ attorney will keep them out of jail to commit even more crime and Chicago crime will rise as schools fail.
    But, you get what you vote for.
    And in Chicago, votes go to the highest bidders.

      1. Well, maybe. The jury hasn’t even convened yet. Even if he does go to jail, and that is a big if, it took more than 40 years.

        He did government work like a mob boss commands his capos. No emails, no text messages, probably limited what he said on cell phone calls.

  20. Paul well done but you’re a bit late.
    You needed to get this message out before the election not after.
    Your campaign for Mayor needed to have players on your team who knew how to get down and dirty.
    Either you or your handlers were afraid to punch back.
    This is Chicago, this is politics. Not for the faint of heart.

  21. I am glad you mention the candidacy of Mariana Spyropoulos over Martinez. I was distressed to see that and support Iris. On the matter of judge elections (I have always been opposed to election of judges) I spend time studying the reviews of the several legal rating groups. I am amazed at the few judges deemed unworthy of retention; I find that hard to believe. Tim Evans always is rated highly but I don’t understand why. I wonder if we’ll ever be able to escape this system and see judges nominated for their worth rather than connections.

    1. “I wonder if we’ll ever be able to escape this system and see judges nominated for their worth rather than connections“

      You know Geraldine, I think that applies to politics/politicians in general, not just judges. In fact, thinking about it, I guess that applies in life not just politics in every way these days too 😢

      1. In many respects, yes. But judges often are not seeking publicity like scions of elected officials often are as they follow in the family footsteps. (I’ve long chuckled at the judicial candidates who have changed their surnames to Irish ones.) Connections matter for sure. Some of the most ignorant people I have worked with keep moving up here in local government because of the father’s position.

  22. Excellent column Paul. Very clear and concise writing. All very true. Some of your one liners rival Kass himself, but you’re just as brilliant. I’ve noticed the low profile of Preckwinkle and other democrats such as Dick Durban. You’re absolutely correct, she leaves no fingerprints behind. Keep up the good fight Mr Vallas, we’re in a deteriorating city, state and country. Problem is, it’s not the concern of the electorate.

  23. You hired Joe Trippi FROM Taxwinkle. He was sent to destroy your campaign and he did with a letter condemning cops right of free speech a week before the election. You and Taxwinkle gave us BLM Brandon.

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