Chicago Mayor Brandon 'Bear of Little Brains' Johnson has to be about to hit the panic button.
He has serious money problems.
And as his only reason for having that big-time gig is to funnel money to his Chicago Teachers' Union overlords and do their bidding, they are bound to be very, very disappointed in their handpicked tool.
The Bear's first, biggest, brightest, and easiest plan to fill his coffers with ill-gotten gains while salving the foam-flecked hordes of progressives screeching for 'the rich to PAY THEIR FAIR SHARE' was his head tax proposal. This little dink on businesses of over 100 employees in the Windy City would be assessed a fee of $21 per employee per month on top of all the other taxes they paid for the *checks notes* privilege of doing business in Chicago.
As you can imagine - and might well have read here, between John and I posting about it - everyone from businesses to people who would like to someday be hired and in between were screaming to the high heavens not to do this.
With someone as mentally insecure as Hizzoner seems to be, challenging his brilliance only succeeds in making him more stubbornly determined to bull his way ahead. And that's exactly what he did, right up to yesterday afternoon, when his proposed head tax, along with fee hikes and several other items, made it in front of the city council for consideration and approval.
The council's answer?
A resounding 'GEDOUDDAHEEYAH, yah bum.' And take your wacky taxes with you.
They crushed Johnson like a proverbial bug, 25 nays to 10 yeas.
BREAKING: Chicago City Council just rejected Mayor Brandon Johnson's proposed revenue package in the Finance Committee: 25 No vs. 10 Yes. That revenue package included Johnson's proposed head tax, along with a long list of fee hikes and new borrowing. This is another stunning defeat (by a large margin) for the mayor and the Chicago Teachers Union's political machine. And it's a win for average Chicagoans who want to see our city grow and thrive. Huge thanks to all of you who contacted your City Council member and told them to reject Johnson's head tax.
— Austin Berg (@Austin__Berg) Nov 17, 2025
What's a teacher's union tool to do?
Well, the Bear still has some tricks up his furry sleeve.
For one thing, people are now just receiving their property tax bills for next year.
This fellow's unhappy because his went up fortyfourhunnertdollars(!) year over year.
Don’t let your alderman vote yes on Brandon Johnson’s ridiculous tax proposal! Make cuts and efficiencies, right size the budget, NO TAX HIKES.
— Ja'Mal Green (@JaymalGreen) Nov 17, 2025
That's a heart attack in an envelope right there, tell you what.
But that's not going to be anywhere near enough, so Johnson is reviving a tax proposal he'd let slide during his fruitless fight for the headtax - a fifty cent per user media tax or a 'cloud tax' as they're calling it.
He first broached this plan back in October, arguing that social media was as addictive as booze or cigarettes, so...why not tax it like those sinful products?
Let's let Facebook, X, and Instagram pay for Chicago's profligacy!
To help close Chicago’s nearly $1.2 billion budget shortfall, Mayor Brandon Johnson is proposing a new tax targeting social media companies. It’s a move no other U.S. city has tried.
“Just like we tax other addictive vices that are bad for our health like nicotine and tobacco, it is far past time to tax social media companies the same way,” Johnson said.
Under the proposal, social media platforms would pay 50 cents for every active user per month. The first 100,000 users would be exempt. City officials estimate the tax would generate $31 million annually to fund expanded crisis response and city-run mental health clinics.
The plan, however, is already facing skepticism, both from City Council and legal experts.
“You’ve admitted that we would be the first in the nation to do this. How confident are we of the city’s legal standing to levy that tax?” Ald. Brendan Reilly (42nd Ward) asked the city’s budget director during a council hearing Tuesday.
Naturally, that received skeptical looks and some sincere snorts of derision, and got lost in the head tax noise in any event.
But like so many very bad, terrible, awful Johnson things...
...it's back.
HOLY SH/T Brandon Johnson the mayor of Chicago has proposed a $.50 tax per active user if the platform has over 100,000 users. He claims the money will go towards mental health. He’s calling to treat social media like tobacco, an addictive vice.
— Brian Eastwood (@BrianEastwood_X) Nov 17, 2025
As this fellow from the Illinois Policy Center explains, Meta and the rest are not going to pay Johnson's tax out of the kindness of their hearts. The end user is going to.
Johnson explains it perfectly, saying he believes his tax scheme 'will generate more progressive revenue.' Oh, you bet it's progressive
He also threw a 'fairness' in there to check all the boxes.
Chicago Mayor, Brandon Johnson, has proposed a “Social Media Amusement & Responsibilities Tax” as part of his $16.6 billion “Protecting Chicago” budget for 2026.
— Patricia (@1109Patricia) Nov 17, 2025
Media and internet free speech advocates Net Choice sent around strongly worded emails this morning, as well as firing off a letter to the Chicago City Council blasting the Bear's blatantly illegal tax plans.
The cloud tax was considered as part of the budget deal that was turned down last night, but might not be as dead as the head tax appears to be. It's just that no one can figure out if it's even legal and how Johnson would collect it.
...Alderpeople have also questioned Johnson’s plan to generate $31 million by taxing social media companies with a tax of 50 cents per month for every active user after the first 100,000 users, under the city’s amusement tax authority.
That money would be used to fund the city’s public mental health clinics and crisis response program, according to Johnson’s proposed budget.
Several alderpeople said they were skeptical that the first-of-its-kind tax, assessed under the city’s amusement tax authority, would withstand a legal challenge, but lawyers for the city told alderpeople they were confident it would be upheld.
Chicago’s 2026 budget does not count on that tax immediately flowing into the city’s coffers, anticipating a legal challenge, officials said.
In a sign that all was right in Johnson's wacky world, cloud taxes are worth fighting for, and those Draft Kings bets from your phone on Sunday games, too, but you'll no longer be taxed on your 'intoxicating hemp products.'
...The budget still calls for the city to impose a local tax on online wagers to generate $26.2 million, but would no longer seek to tax the sale of intoxicating hemp products.
Oh, goody. At least they've got their priorities straight.
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