Illinois is a Financial Wreck. So is Chicago. And So is the Public School System.
In case you have not noticed, Illinois, my ancestral home is on the economic skids. Illinois is financially crumpling. A major weight dragging it down is Chicago. And the Chicago public school system is almost beyond rescue.
Let us start with the economic disaster besetting the Land of Lincoln.
Oh, what a glorious progressive paradise Illinois has become under the tender loving care of Governor J.B. Pritzker and his woke Democrat machine. The “Land of Lincoln” is now the Land of Endless Tax Hikes and Business Flight. Since Pritzker waddled into office, the state has slapped on more than 57 tax increases and fees, sucking another $77 billion-plus from the pockets of working stiffs and job creators. His latest 2026 budget masterpiece? Nearly $600 million in fresh business tax hikes, including caps on net operating losses and sales tax credits that will cost companies over $800 million. Because nothing says “welcome to Illinois” like making it hostile to anyone trying to run a business.
Progressive and woke policies haven’t just made the state economically “unsustainable”—they’ve turned it into a fiscal black hole. Sky-high property taxes, corporate mandates, and virtue-signaling regulations have driven out Boeing, Caterpillar, Citadel, and countless others to low-tax red states like Texas and Florida. Illinois has suffered a net exodus for years. Taxpayers are voting with their U-Haul trucks while Pritzker preens about “balanced budgets” that somehow always require more money from the little guy.
And then there are the pensions—the sacred, untouchable golden goose. Illinois is saddled with roughly $144 billion in unfunded liabilities, the worst pension crisis in America. Why? Because the geniuses who wrote the 1970 Illinois Constitution included a “pension protection clause” that makes benefits an enforceable contract that “shall not be diminished or impaired.” Courts have ruled that it protects not just what workers earned, but every future perk and 3% compounded cost-of-living raise forever. No reform, no cuts, no common sense. Politicians promised the moon, kicked the can down the road with the 1994 “Edgar ramp,” and now taxpayers get to foot the bill while essential services get starved. Pritzker’s crowd loves to lecture about “fairness,” but somehow, it’s always fair to bleed the productive working class dry for union retirees. What could possibly go wrong has … gone wrong.
Then there is Chicago.
The Windy City isn’t just on the edge of economic collapse—it’s doing cartwheels toward the abyss, led by Mayor Brandon Johnson, the former Chicago Teachers Union organizer who treats the city budget like his personal slush fund for woke experiments.
Chicago’s 2026 budget was a clown show from start to finish. Johnson floated a “Protecting Chicago Budget” stuffed with new taxes on large corporations, Big Tech, and the ultra-rich—because nothing fixes fiscal mismanagement like punishing and pushing out the people who create jobs and revenue.
Johnson wanted to protect pet programs funded by expiring federal COVID cash while ignoring the $1.2 billion gap. City Council pushed back and passed a $16.6 billion plan without his full head-tax fantasy, but Johnson called it “morally bankrupt” anyway. Result? A projected $163 million shortfall and warnings of a mid-year crisis. Overspending has exploded 62% since 2019—twice as fast as other big cities—while revenues hit record highs. The problem isn’t too little money; it’s too much progressive spending on “equity,” “community safety funds,” and every social justice gimmick under the sun.
This is the same Democrat machine playbook that turned Detroit into a bankrupt ghost town — with endless taxes, union sweetheart deals, crime-friendly policies dressed up as “reform,” and zero accountability. Johnson’s crowd obsesses over taxing the rich and expanding mental health vans while businesses and residents flee to the suburbs or out of state. Property taxes? Sky-high. Crime? Still high – especially in the segregated minority ghettoes. The city is hemorrhaging people and employers, yet the mayor doubles down on the very policies killing it. Chicago isn’t broke—it’s being looted by its own leadership. Thanks, Brandon, for showing the world what woke progressivism looks like.
And finally, the Chicago Public School System.
This one is close to my heart because I served as senior consultant to the school board during a brief period of genuine reform. If you thought the state and city were disasters, wait until you see the Chicago Public Schools—where the financial crisis is measured in hundreds of millions of dollars and the educational outcomes in single-digit proficiency rates.
Chicago Public Schools just announced a whopping $732.5 million budget deficit for the 2026-27 school year. Enrollment has plummeted by 45,000 students. This follows years of protecting teacher and principal jobs. The schools suffer from overly friendly union contracts with the Chicago Teachers Union—4-5% raises, bloated benefits, and ironclad protections that treat every kid as a revenue stream. The so-called “Children’s Budget” has been suffering for years from cuts in supplies and elimination of music and art classes. Why? Because the adults in the room—union bosses and their Democrat enablers in City Hall—put themselves first. Aging buildings, massive debt service, and skyrocketing special-ed costs eat everything while classroom funding gets squeezed.
And the quality? Abysmal—especially for Black and Latino students, who are trapped in failing schools at rates that would make any real civil rights activist weep. Decades of “progressive” education have produced generation after generation of kids who can’t read or do math at grade level. I have written about this moral atrocity for years. The system condemns minority children to poverty and failure. And keeps them trapped in the segregated ghetto after they (if they) graduate.
The one real solution—school choice—gets rejected every time. Why? Because every kid trapped in a failing building means more money, more power, and more votes for the unions and the Democrat political machine. There is a reason why the major education unions are the biggest donors to the Democrat political machines. They’d rather beg Uncle Sam (and now, apparently, Springfield) for bailouts than let parents get their kids in better schools at less cost to the taxpayer. Trump would be crazy to send a dime. Why fund a system that prioritizes union dues and political donations over children?
Illinois, Chicago, and the Chicago Public School System stand as an economic trifecta for the failure of progressive and woke policies. It is a failure that destroys economic vitality fiscal sanity, and any hope for a successful future. High taxes, untouchable pensions, union strangleholds, identity-politics spending — and a refusal to let markets or parents drive the economics — have created a vicious cycle of deficits, debt, and decline. Businesses and taxpayers aren’t fleeing because they hate the weather—they’re escaping the consequences of Democrat governance. Until voters finally wise up and reject the Democrats cynical policies, people of the Land of Lincoln, the Windy City and the students of Chicago schools will keep crumbling under the weight of its own failed ideology.
So, there ‘tis.
Why does Larry write all these stories that no one reads but attacks those who faithfully read? It’s a paradox.
NJ is a founding colony and where I live and was born. It has seen many ups and downs over the years and many of the same issues as Illinois. Worse yet, we’re in the shadow of NYC and Philadelphia and whatever issues they have at any given time. It’s part nature, and part nurture and it will happen no matter what policies are in place. Where I was born, you would be rightfully afraid to walk today. Newark was dead in the recent past, today it’s a hotspot for culture and entertainment. Camden ruled dead, still survives, and even touts’ revitalization now. Things ebb and flow.
Illinois is ebbing, even circling the bowl, but not flushed yet. This is most certainly on the Democrats watch. However, even there, there was four years of Republican control of the Governor’s house and that neither changed anything or gave people a better reason to vote Republican. And they didn’t. The Republicans failed to change their minds when elected.
One issue we all face, everywhere, is that the folks we elect have a prime responsibility to manage budgets. Chicago and Illinois have failed that task, they even cheat, and they keep getting elected. I believe we should elect folks specifically to watch the dollars and fire them when they fail that task. Spend wisely for good returns. Take prudent loans, when viable and legal, as part of that management. Become unelected when they fail. I believe that balanced budget amendments erase a major part of that responsibility and, for a long time, stood against them as the easy idiot’s way out. Today, I give up on expecting fiscally responsible politicians and support balanced budget amendments (BBA) at the State and Local levels. These guys can’t manage finances so fuck em. With the BBA the bottom line is constitutionally mandated and OK. (in a perfect world they should be able to borrow into deficit, but these schmucks can’t be trusted to do the math to handle a loan).
All BBA versions have some loopholes; Illinois’s version is probably the worst in the nation, and Pritsker can legally cheat because of it. And he does. I agree with Larry, this is a financial disaster caused by Democratic programs and policies but it does not mean all Democratic programs and policies are bad. Something is wrong in Illinois though – on the money. Not that the programs are wrong in Illinois, but they are MOST CERTAINLY, at minimum, managed poorly. Pretty sure they sucked under the Republican governor too.
At the Federal Level, I am confident that the numbers show Democrats better at budget management than Republicans. The fact that Maga owns the yugest deficit ever pretty much sets the stage for that. Trump is very bad at managing the budget. Biden lowered the defic it rate of increase for consecutive years; Trump only increases it. He cheated in 2025 by adding his taxation-without-representation tariff revenues to squeak by Biden’s worst of three years; without the tariffs, 2025 Trump deficint sucks pondwater.
The bill for his vanity projects alone is astounding, unfair to citizens with meager returns for the expense. All over budget and off schedule too.
That said, there are external factors that, of course, Larry ignores in his bashing of Democrats in Illinois and elsewhere. Covid, immigration changes, even gun control affect Chicago. As goes Chicago goes Illinois, much of the rural too, which is Red. Don’t matter, still the blame of the Democrats even for the Red region.
The covid story is they got covid bucks to buffer their budget and spent/managed it as if it would be forever. Well, the covid buffer ran out, they don’t have increased tax revenues to cover and now they be in the shitter. So, not their fault, but it is their fault as well. They should have seen it coming and managed to it.
They are “floated” by immigrants, especially as blacks move out to suburbia. Hey, blacks moving out, that’s a plus, right? They have enough money to move out! As immigrant families shrink, again the revenues, school enrolls, all suffer and Chicago again did not manage to it.
There’s a lot of this shit going on, a confluence of bad numbers, it’s on Democrats watch and they appear not to be watching.
I mean they cry about high property taxes, hey, NJ can beat that and we’re still financially viable. Incidentally, this forces Illinois and NJ to constantly backfill for seniors who leave in droves. Yes, it bothers us and Chicago too because, like Larry, when you retire, you leave just for the tax dollar benefits. From NJ, I can make four digits, close to five, just by crossing the border. Any state. I claim NJ is no country for old men. And every year, people like Larry tell us of the great NJ migration. He’s wrong twice. NJ and Illinois populations are growing. For Illinois, very small, and just the past two years, but it’s a turnaround trend. NJ is a bit ahead of that and has been growing always. Just the data skimmers like Larry that see different because they cherry-pick data sources. It’s complex and nuanced. Both NJ and Chicago have old folks leaving. To come to both places, you better be top or bottom of game. As in you better be able to either make some cash OR live in a higher density, lower rent, deal like x families to a house. Thus, young, educated, professionals and immigrants. Both NJ and Chicago thrive on immigrants who are willing to live a little tighter to chase than American dream. In Chicago, many inner city blacks have arrived at the first step of the American dream and are moving to the suburbs. Thus a black exodus from the city proper. The immigrant influx is slowing, the birth rate for immigrants is dropping, and the result was a population drop in the city which is stabilizing now: ebb and flow.
School systems are the similar. In NJ we pay, but we get the best in return. Nuff said except take all your great ideas for school change and shove em for NJ. We are number one, copy us! For Chicago, I have added a piece unravelling the complexity for schools, and it’s still tough. Blacks are leaving, whites are staying, immigrants have smaller families. I think 8 out of ten kids are in public schools and there’s much budget problems. In High Schools, Chicago has Northside Prep, Payton Prep, and Whitney Young — all top schools, I think magnet. Chicago also boasts five or six top rated school districts.
Interestingly, no middle schools or elementary are top rated, and no schools outside Chicago and throughout Illinois are top rated which includes the “red zones” outside the city. Not like Republicans doing it better there. But like I said, nuanced.
This piece talks on schools and notes many deficiencies; political party is not one of them. There is no doubt that with less enrollees, the fixed cost per student skyrockets and it’s on the Democrats watch to manage. Gonna have to dump some assets to right size this ship.
This is a good read, even for Larry: *https://kidsfirstchicago.org/publications/enrollment-crisis* It’s focusing on root causes.
Another great read is from the Illinois Policy Institute; perhaps Larry already has in that they dovetail many of his concepts. However, this nonpartisan group, started by Republicans two decades ago, does not call out Democrats as being bad. It does point out issues with programs, many of which are from Democrats. I know, a nit, but folks —- tis the programs and policies we need to attack, not people. It does seem clear from this review of the programs, that Pritzker should be voted out. He has failed on the financials. *https://www.illinoispolicy.org/reports/illinois-forward-2027-how-to-fix-illinois-state-finances/* Pretty sure this one gives Larry some more factual ammo for his partisan cannons.
Gotta say this like Abbot and Costello…. “Hey, LAAAAAAAAAArry,” here’s a creampuff for your delight.
*https://www.usnews.com/news/best-states/rankings/fiscal-stability*
Just pair it up against a red/blue map; think you come out better as you claim #1, we get #2 and #3 but we also get #49 and #50 and NJ be 49. Course you cover the waterfront bottom after that. Illinois number $50 with a bullet.
It’s financial stability only, our pension is a killer, and overall we rate pretty good. But on financials, we suck. Thank goodness your Illinois is there to soften our blow.