Inquiring minds want to know: Who’s paying for the massive direct-mail campaign on behalf of the Chicago Teachers’ Union candidate for president of the Chicago Board of Education?
Around the Chicago Contrarian press room, we relish the seemingly endless opportunities to ridicule the clowns “running” (actually ruining) our city. But Providence rarely delivers a political candidate whose very name seems tailor-made for satire and ridicule.
In this case, the gift from on high (or perhaps the deepest circle of Hades) is Hilario Dominguez, the Chicago Teachers’ Union (CTU) candidate for president of the Chicago Board of Education. Around here, we’ve decided to call him Hilarious Dominguez, because his campaign is shaping up to be one of the biggest jokes in Chicago politics, and that’s saying something in a city that elected Brandon Johnson mayor. If you thought the notorious MBJ was the biggest tool imaginable of CTU President Stacey Davis Gates, wait until you meet Hilarious. Johnson at least occasionally manages to create the appearance of independent thought. Dominguez doesn’t seem particularly interested in even pretending.
Like most of the jokes running this city, he would be funny if it wasn't so sad, and if the joke wasn't on us, because these thieves and scoundrels are ruining the city for their own benefit financially at your expense.
The notorious SDG already has a former CTU political organizer occupying the mayor’s office. Now she wants another former CTU political operative presiding over the Chicago Board of Education, the institution that is supposed to oversee the school system and exercise independent judgment over matters involving the union. Think about that for a moment. The union that negotiates with the school district wants one of its own political operatives sitting at the head of the board responsible for overseeing that district. You got it. She wants to sit at both sides of the negotiating table, essentially negotiating with her own bad self. How stupid do you have to be to fall for this kind of obvious conflict of interest?
Anybody who votes for Hilarious might as well just take their money and light a match to it, because it's all going in Stacy Davis-Gates' designer purse. This isn’t merely a potential conflict of interest. It’s an invitation to turn the whole concept of independent governance into a punch line. Dominguez is a former CPS special education teacher, who subsequently became a CTU political director (in other words, a political operative). His more recent professional experience raises an obvious question: Is he seeking this office to represent the public, or to represent the union whose political operation helped launch his candidacy?
Which brings us to the latest exhibit in this political comedy. What should arrive in your humble correspondent’s mailbox but a big, old-fashioned, two-sided campaign mailer announcing that “Hilario Dominguez Has a Plan.” The piece is paid for by an organization called “Friends of Hilario Dominguez.” Well, gee, who might these friends be? Let me take three guesses. On second thought, I won’t need the last two. The Illinois State Board of Elections provides a rather illuminating answer.
Campaign disclosures show political action committees associated (wait for it) with the Chicago Teachers Union have provided substantial in-kind support to Friends of Hilario Dominguez, including consulting, contractual services, staffing, and media production. One August filing alone identifies a $33,966 contribution for contractual services, along with numerous other expenditures. The CTU also proudly lists Dominguez among its endorsed candidates. These records don’t establish who paid for the particular mailer that landed in my mailbox, but they certainly establish that the union’s political organizations are among his significant benefactors. What a surprise! The organization seeking influence over the school board is helping finance the campaign of the man who wants to preside over it. The fox is guarding the henhouse to protect the failure factory we know as CPS from any real governance.
Now let’s examine the actual propaganda, because Hilarious has graciously provided us with an excellent illustration of everything wrong with the way Chicago approaches public education. The front of the mailer announces his grand plan to “Invest in Our Children.” Well, who could possibly object to that? Everybody wants to invest in children. It’s the kind of political language that sounds wonderful until somebody asks what the so-called “investment” costs, who benefits, and whether the children are actually learning anything.
Then comes the real agenda: “School Closures Don’t Work.” There you have it, folks. In the world of Hilarious Dominguez, apparently no school should ever close, regardless of how few students attend it, how much it costs to operate, or whether its students could receive a better education somewhere else. And this isn’t merely campaign-mailer exaggeration. In a Chicago Sun-Times candidate questionnaire, Dominguez answered no when asked whether he would support closing schools for any reason. Any reason! What if all the students disappeared? Nope. Keep them open and fully staffed at taxpayer expense until all of them disappear too. Hilarious doesn’t care! ‘Cuz he’s special — as in special education! Everybody gets a prize — as long as they’re card-carrying CTU members — the prize being a no-show, do-nothing job of the sort that political bosses used to reserve for their idiot relatives in Streets and San, rather than supposed learned professionals to whom the city’s future, its children, were entrusted.
You, the taxpayer? You get the booby prize. You get to hold the bag, pick up the tab. It’s the stupid tax on anybody who falls for this clown’s reeking BS, and they richly deserve it for falling for this scam artist and his grifting bosses.
Imagine applying that philosophy to practically any other institution in American life. Businesses would never close unprofitable locations. Hospitals would never consolidate underused facilities. Churches would never merge congregations. Apparently the laws of economics, not to mention arithmetic, have been repealed by the Chicago Teachers Union. Maybe that’s why they don’t teach them in our woke schools.
For an example of how rational institutions respond to declining enrollment, consider the Archdiocese of Chicago. Catholic schools have experienced substantial enrollment declines over the decades, and the Archdiocese has faced painful decisions about maintaining schools that no longer have enough students to operate economically. What does it do? Does it insist that every building must remain open forever, regardless of the financial consequences? Of course not. It closes or consolidates schools when necessary, sometimes combining two struggling institutions into one stronger school. These decisions can be heartbreaking for parents, students, alumni, and parishioners who love their neighborhood schools. But the Archdiocese understands something apparently beyond the comprehension of Hilarious Dominguez: Cities and states can’t print money and Donald Trump ain’t going to send Chicago schools a dime. Buildings cost money. Teachers cost money. Administrators cost money. And every dollar spent maintaining excess capacity is a dollar that cannot be spent improving education.
Catholic schools also operate under a discipline largely absent from the public system. Parents pay tuition, parishioners contribute donations, and families can vote with their feet. The schools must continually justify their value to the people supporting them.
The Chicago Teachers Union operates in a rather different universe. When the money runs short, the answer is invariably more money. More state funding. More city funding. More taxes. More borrowing. More of everything except accountability for results. CPS has a budget approaching $10 billion, yet somehow the solution to every problem remains another infusion of taxpayer cash.
That, of course, explains why our mayor vetoed the city council's feeble attempt to put some sort of a cap on his endless borrowing, which is mortgaging our future and the future of the children that CPS is systematically abusing by generating generation after generation of imbeciles. MBJ, SDG, and Hilarious think that they've got some kind of an American Express black card with no credit limit. They must think Chicago has the equivalent of a Federal Reserve that can just print money out of thin air. Well, guess what? The bond market begs to differ. At some point, they're gonna call in the marker, and you're going to watch this city fall into the lake like the Twin Towers on 9/11.
The union’s political allies speak endlessly about investing in children, but the interests of children and the financial interests of the “adults” who are “employed” by the school system are anything but aligned. Sometimes they coincide, when the teachers' union gives them the day off school to go and protest for more money, more money, more money. Sometimes they don’t. A school district’s responsibility is to educate children, not to maintain a permanent employment program for adults. When a school becomes so underenrolled that it cannot provide a full range of academic opportunities, maintaining that building may actually shortchange the students it supposedly serves.
Dominguez, however, has an answer. According to his mailer, closures hurt students and communities and cost millions. Now there is a claim that deserves some scrutiny. Just how do they cost millions? Doesn't keeping empty schools fully staffed cost millions? Now, it's stupid to keep the buildings there, but we all know why they're keeping the buildings — because they want to reopen them and turn these empty schools into zombie schools that don't educate anybody but line the pockets of CTU members and thus the pockets of the union. That's all the union cares about: dues, dues, dues, so they can give Stacy a bigger and bigger salary.
And now she's double-dipping because she's head of the Illinois Federation of Teachers (IFT) too. It's good to be the Stacy. It's good to be the queen of mean. But it's not so good if you have to pay the queen the taxes she needs to pay for her stiletto heels and designer purses. She spends as little time as possible educating children.

Naturally, the unholy trinity of MBJ, SDG, and Hilarious plays the dog-eared race card. Many of the affected schools served predominantly Black communities, and critics have raised legitimate questions about the consequences. That’s because the system has lost 50 percent of its black students, who have fled from the terror-towns their neighborhoods have become due to an abdication of law enforcement by progressive Democrats siding with criminals vs. their victims, nearly 9 out of 10 of whom are people of color, and who have deserted the schools that preach but don’t teach, preaching the siren song of socialism like a secular religion. But none of that establishes keeping every under-enrolled school open indefinitely is good educational policy — maintaining excess buildings, staffing, and infrastructure also costs money.
The sensible question is not whether every closure is good or every closure is bad. It is whether a particular consolidation will improve educational opportunities while using scarce resources responsibly. That’s the sort of judgment school board members are elected to exercise. By contrast, elect Hilarious and the fix is in.
Flip the mailer over and we discover another revelation: “Our Schools Are for Our Communities.” Really? Who would have guessed? But in reality, this is just another bald-faced lie. As far as Hilarious is concerned, the schools exist for the benefit of the teachers, not for the students, and certainly not for the taxpayers.

Then comes the claim that Dominguez is the candidate with a plan to fight for neighborhood schools. But fighting for neighborhood schools is not necessarily the same thing as fighting to keep every neighborhood school building open. A school with dwindling enrollment may struggle to offer the academic programs, extracurricular activities, and specialized services available at a larger institution. Consolidation, when carefully planned, can sometimes produce a stronger school for the children who attend it. Dominguez’s categorical opposition to closures effectively removes that option from the table. That’s not a plan. That’s a political commitment to one particular outcome, regardless of the facts.
The mailer then invokes what amounts to ancient history: The 2013 closures under Emanuel: “Families fought. Parents organized. Communities spoke up.” Fair enough. Those communities deserved to be heard, and there are legitimate criticisms of how the Emanuel administration handled the process. But the lesson should be that school closures require transparency, sound planning, community participation, and an honest assessment of educational outcomes. Instead, Dominguez appears determined to turn the experience into a permanent prohibition against closing schools. That’s like deciding that because a hospital once botched an operation, surgery should be outlawed. It is political theater masquerading as educational policy, designed to appeal to people who understandably fear losing their neighborhood institutions while avoiding the much harder question of how Chicago can afford to operate its school system.
And there is another little detail that taxpayers might find interesting. According to the Sun-Times candidate questionnaire, Dominguez supports continuing to raise the CPS property tax levy to the maximum each year. His position on school closings is "No," under any circumstances. His position on maximizing the property tax levy is "Yes." What a remarkable coincidence! No closures, no retreat from maximum taxation, and a political campaign receiving substantial support from organizations affiliated with the teachers' union. The voters might reasonably wonder whose interests will prevail when those interests collide. Dominguez would undoubtedly argue that better-funded schools serve children and families. That’s a legitimate argument to make. But so is the argument that Chicago families, already struggling with property taxes and the cost of living, deserve a school board willing to distinguish genuine educational investments from expenditures that primarily preserve the existing bureaucracy.
The larger problem is Chicago is increasingly becoming a city in which organizations receiving public money exercise extraordinary influence over the politicians responsible for deciding how that money is spent. The notorious MBJ emerged from the CTU’s political apparatus and now occupies the fifth floor of City Hall. The notorious SDG remains one of the most influential political figures in the city. And now Hilarious Dominguez, another product of that apparatus, wants to preside over the school board. The result threatens to become a closed political loop in which the same interests influence both sides of the negotiating table, while taxpayers are left to pick up the bill and students wait for better results.
So who are the Friends of Hilario Dominguez? The complete answer requires examining the campaign’s financial disclosures, including the sources and amounts of contributions and the actual expenditures behind its direct-mail operation. But the public records already establish substantial CTU-affiliated financial support, and Dominguez’s own policy positions make clear why the union would find him an attractive candidate. Chicago voters should ask a very simple question before putting him in charge of their school board: Will Hilarious Dominguez be an independent guardian of public education, or another political guardian of the Chicago Teachers Union?
If his campaign literature is any indication, the joke may ultimately be on Chicago’s taxpayers. And there’s nothing hilarious about that.
George Shay is a conservative activist and writer. You can find his Common Sense Substack here.

