“You can’t tax yourself into prosperity.”
— Milton Friedman, University of Chicago
Let’s be clear: Chicago isn’t just flirting with economic suicide — it’s serving it up as policy.
Mayor Brandon Johnson’s latest “budget innovation” is a $21-per-employee corporate head tax on businesses with more than 100 employees — the very firms that still have the courage to operate in a city famous for crime, corruption, and collapsing infrastructure.
This so-called “Community Safety Fund” isn’t about safety or community; it’s about redistributing private earnings to cover decades of failed city management.
Milton Friedman, Chicago’s most famous economist, used to warn: “You can’t tax yourself into prosperity.” He also reminded us that “the society that puts equality before freedom will get neither.” Chicago seems determined to prove him right again.
Taxing Job Creators for Existing
This head tax — $21 per worker, every month — is a tax on employment itself. It punishes hiring, penalizes growth, and tells every job creator: “The bigger you are, the more we’ll take.” That’s not progressive policy — that’s regressive economics.
The levy would hit roughly 3% of companies citywide — the very ones responsible for most private payroll in Chicago. The city’s message to employers is crystal clear: if you hire more than 100 people, you’re now a target.
Rahm Emanuel — no conservative — eliminated this same tax in 2014 because he called it a “job killer.” And he was right. Chicago lost jobs, investment, and population under that old tax. So what’s the city doing now? Bringing it back — and pretending it’s progress.
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The Friedman Test
Milton Friedman taught that inflation, deficits, and government growth all come from one source: politicians spending other people’s money. Brandon Johnson’s plan could be a case study in what Friedman called the fatal conceit of planners — the illusion that they can direct prosperity better than the market.
The mayor’s budget brags about not raising property taxes or grocery taxes — as though that’s some kind of fiscal virtue — while quietly hitting employers with $617 million in new taxes. It’s sleight-of-hand economics: take from producers, claim compassion, and hope nobody notices when businesses leave.
When Friedman ran the numbers on government spending, he found the only effective brake on waste was limiting revenue. Give bureaucrats more, and they’ll spend more — always in the name of “equity,” “safety,” or “community.” The labels change. The result never does.
Chicago’s New Religion: Punish Success
Under Johnson, the city’s moral compass points due left. If you’re successful, you’re guilty. If you create jobs, you owe penance. And if you invest in Chicago, prepare to pay for the privilege of staying.
They call it a “Community Safety Fund.” But anyone with an Econ 101 background can see it’s a political slush fund to replace expired federal handouts. The pandemic relief money is gone, so Johnson’s hunting for the next pot of gold — and he’s chosen the private sector’s wallet.
This is how socialist thinking always works: when Washington’s checks stop coming, local governments start shaking down the productive class. It’s redistribution under new branding — same math, same misery.
The Real Way to Fix Chicago
Friedman’s Chicago School didn’t make this city famous by taxing innovation. It made it famous by celebrating free markets, low taxes, and open competition. If Brandon Johnson really wants “community safety,” he should start with economic safety — the kind that comes from employment, entrepreneurship, and investment.
Imagine if City Hall cut red tape instead of adding taxes. Imagine if Chicago became a hub for manufacturing again by lowering costs, not raising them. Imagine if the city trusted its own citizens — instead of trying to micromanage them with tax-funded programs that never deliver results.
Milton Friedman’s ghost must be pacing along Lake Michigan right now, muttering, “There is nothing more permanent than a temporary government program.” And he’s right again — Johnson’s “Community Safety Fund” will outlast its promises, underperform its goals, and keep draining the private economy long after the mayor has moved on.
Capital Flight Is Coming
Let’s call this what it is: a jobs tax in disguise. Chicago already faces an exodus of residents and companies to places like Florida, Texas, and Tennessee — states that understand prosperity is built by the private sector, not the public one.
If Johnson’s plan passes, even more businesses will flee. Not because they don’t love the city, but because you can’t build a future in a place that punishes success.
Chicago’s decline isn’t inevitable. But under policies like this, it’s accelerating.
As Friedman would say — “The only way to help the poor is to make the rich less necessary.” Brandon Johnson is trying to prove that by chasing the rich away entirely.
Bottom line: Chicago doesn’t need a new head tax. It needs new heads — ones that still believe in growth, competition, and freedom.
Until then, Chicago will keep learning the same old lesson — you can’t tax your way to opportunity.