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.