The Twin Billionaires Who Are the Real Policy Failures in Chicago

August 25, 2026

There’s a sick Game of Thrones going on in this town. The two queens who reign over hapless Chicagoans are bleeding their helpless subjects dry

You know, the DSA types really love to talk about how billionaires are evil enemies of the people, that they’re policy failures, and that they must be brought down. In fact, Byron (recently nicknamed “the notorious BS-L,” aka “Squeaky”) Sigcho-Lopez’s Wife #2, who is arguably a downgrade from Wife #1 (who busted him for dissipating family funds through prostitutes and porn, and all sorts of other unfortunate character flaws), actually was caught on cam the other day talking about the fact that if the DSA doesn’t get what it wants through ballots, it will get it through bullets. This was in reference to yet another outrageous demand by the Chicago Public Schools (CP$), which strives to be the most expensive system on a per-pupil basis in the history of education while having the lowest return on that exorbitant investment.

Which brings us to the culprits in this immorality play. There are indeed two billionaires afflicting our fair city who are policy failures: The Cook County government, led by Boss Toni Preckwinkle, and CP$, which is, for all practical purposes, ruled by Queen Stacey Davis Gates, the thin-skinned, thick-headed head of the Chicago Teachers’ Union (CTU), and now president of the Illinois Federation of Teachers.

So we have to commend our reigning Queen for the success of an essentially Hitlerian approach to empire building: “Today Chicago, tomorrow the world.” Her variation on that Wagnerian theme: Today Chicago, tomorrow Illinois. Who knows? Given her seemingly limitless appetite for misrule and greed at the expense of the helpless students and parents who are her long-suffering subjects, it would hardly be surprising if she has national ambitions. Imagine the dues revenue if she goes nationwide. More money, more money, more money.

So there we have it: The twin deca-billionaires impoverishing their helpless, hapless victims — the citizens, taxpayers, and voters unfortunate enough to live in the city of Chicago, County of Cook. Both of these incredibly incompetent, union-captive entities are sucking the taxpayers dry, and both of them, just by coincidence apparently, have $10 billion budgets. Yep, folks, that’s 10 billion with a B. If you want to talk about a multi-billionaire being a policy failure, there you have it in the person of two Queens crushing the city and county with their incredible greed and lack of regard for the constituents they claim to serve.

These two queendoms are literally joined at the hip. They share a palace that occupies a whole square block of primo real estate on which no taxes are paid. To paraphrase the late Leona Helmsley: Taxes are for the little people," the serfs who cower like Saxon subjects of their Norman overlords in the high tower. The County Building is chock-full of nuts: Payrollers, incompetent, do-nothing political stooges. Of course, that’s only to the extent that they even bother to show up. Much like teachers, they tend to be guilty of truancy, whether you call it working from home, sick days, or what have you. There are many ghosts in that building who still manage to collect their paychecks week after week, month after month, year after year without providing any value whatsoever to the taxpayers. They fall under the oxymoronic title government “workers.”

And now, of course, the CTU might as well move in, because for all practical purposes, Mayor 6.6 percent, Brandon Johnson, is a wholly owned subsidiary of Davis Gates' CTU. We used to say in Chicago: “We don’t want nobody nobody sent.” Well, Stacey Davis Gates sent Brandon Johnson. Somehow, not only did he win the election to replace an incumbent mayor who, granted, was a train wreck, but he also managed to make her look good by comparison, which I thought was impossible. The brainwashed, brain-dead DSAocrat zombies chose the fool over the most qualified mayoral candidate in the history of the city, namely Paul Vallas, who continues to valiantly fight on for the interests of the taxpayers and voters even though, forgive them Lord, they know not what he does.

The failures of the Chicago Public Schools live in infamy: Abysmally low test scores, delivering an almost negative return on investment for the exorbitant price of $40,000 per pupil, with more to come amidst even more demands from the state of Illinois for funding. And that’s going to be paid by whom? You, the taxpayer. No matter where you live, even if you don’t live in Chicago, you’re going to pay. As long as you stay within Illinois, they’re going to suck you dry.

Or we could rally and vote for a school board in Chicago that would throw these bums out, or shut them down at least. You CAN say no to the teachers. And if they want to go on strike, who cares? They’re not there much anyway. In the 2024–2025 school year, 43.2 percent of Chicago Public Schools teachers were chronically absent, meaning they missed 10 or more days for non-professional-development reasons. That’s why we taxpayers have to pay substitute teachers to the tune of $50 an hour in addition to the salaried teachers who are AWOL. CPS historically registers spending of roughly $42 million annually on substitute teachers.

Then again, the students don’t make a habit of showing up either. Chicago has got to be in contention for the truancy capital of the world. Chronic absenteeism across CPS hovers around 40 percent, meaning roughly four out of every 10 students miss 10 percent or more of the academic year. Of course, there are no consequences for this sort of behavior on behalf of either teachers or students.

There is no education going on in this town of any magnitude, at least not for most of the kids. There are points of brilliance. Even Kennedy High School has a fantastic program for honor students. But the vast majority of these kids are not being served properly. And of course they’ll cry about the raw material, but you know what? You can’t get different students. You’ve got the students you got. It is what it is. And if you’re going to have dismal outcomes, turning out basically illiterate and innumerate “graduates,” to use the term loosely, you might as well at least cut the cost of educational malpractice.

Why not invest in roboteachers? Instead, the unions are fighting the use of artificial intelligence, which could automate a lot of the educational system. Elon Musk has promised us a world in which artificially intelligent robots will basically liberate us from the need to work and provide us with heaven on earth. Is that going to happen? I don’t know. But it sure seems to me that teaching kids to use AI and learn with AI is what’s going to prepare them for the brave new world, not trying to ban it — and honestly, not trying to ban cell phones. These kids are going to be living on cell phones. Try to get a job. Try to do a job. You’re going to need one.

What you have to do is discipline the children, and that’s what the system does not do. They can segregate the best and brightest and educate them. Kudos for that. But the challenge is educating students who are not uneducable but are very challenging to deal with. In that, the system is obviously failing miserably, and you can tell that by the test scores. That’s why the unions want to abolish the tests and teaching to the test: then they’re not accountable.

Until Elon’s Brave New World comes, we had better be preparing these kids for the tough world out there, or they’re going to lead a life of misery and become susceptible to the seductions of the socialists, of the DSA, like BS-L, for example. And that will lead to the deluge. So we must start educating these kids so they can survive and thrive in the world we live in. And if Elon’s new paradise comes, more power to him. But if not, we’ll have a population that can not only endure the slings and arrows of outrageous fortune but resist the siren song of socialism.

Now let’s get to the county. The county is completely incompetent. They cannot get property tax bills out on time. They’ve been working on systems development to “improve things” for ten years. The system is dysfunctional. There’s no end in sight. This is a county that can’t even collect money, which might be just as well, frankly, because God knows what they do with it. It’s overstaffed. It’s got featherbedding. It’s got payrollers who do nothing, and it just gets worse and worse and worse. More money, more money, more money.

So these are the twin towers of policy-failure billionaires, and we just keep reelecting the people who run them. We keep reelecting Toni Preckwinkle. We elected Brandon Johnson, who ultimately is in charge of the schools, except the schools are in charge of him. The inmates are running the asylum, and it’s got to stop, folks. That’s our job here as contrarians. We have to get out and vote, and it starts with the Ides of March. We have to get rid of Brandon Johnson. We have to keep people off the Chicago School Board who are allowing Stacey Davis Gates to run roughshod over the entire city.

Unfortunately, it looks like the Grim Reaper is going to be the only entity that can eliminate Boss Toni, who will become an octogenarian next St. Paddy’s Day. Astonishingly, given her stupefying incompetence, she is running unopposed because we live in a one-party city and a one-party county that make North Korean elections look suspenseful. It’s an atrocity, and we’re all paying the price every day. If we don’t change it, then all of us blessed with a modicum of common sense are going to have to find someplace else to live. That would be a tragedy, because this was a once-great city, and it could be great again if we would just vote the right people into office who would do the right thing, act with goodwill, and take on the tough challenges, including the gangs.

You might as well include among the gangsters Stacey Davis Gates and Toni Preckwinkle, because they’re just shaking us down, folks. There’s no way these two bureaucracies should cost us ten billion dollars each. Spare me. If Elon Musk is a trillionaire, that’s fine by me, because he isn’t getting that money out of my pocket. Toni Preckwinkle and Stacey Davis Gates are.

I don’t know about you, but that’s not OK with me.

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