WORST DEAL OF ALL TIME? Chicago's Infamous Parking Meter Deal Is Back In The News After It Just Sold To ANOTHER Private Company, And Not The City Of Chicago, For A Cool 3 Billion Dollars
NBC Chicago - Chicago Mayor Brandon Johnson said the city is not, in fact, going to buy back the 36,000 parking meters it sold to a private company 18 years ago. However, a change in ownership could still be on its way after the meters were sold to a different bidder.
"I want to put the rumors to bed: We are not pursuing the purchase of the city's parking meters at this time," Johnson told reporters Tuesday.
At the height of the 2008 financial crisis, a group of investors paid nearly $1.2 billion dollars for Chicago's parking meters for 75 years.
The meters went up for a bid last summer, and multiple bidders, including the city, were interested. Johnson confirmed the city did look at a potential deal but decided against it. His team ran the numbers and decided it doesn't make financial sense.
"The final purchase price is far too high, much more than we initially received for the sale and higher than most reasonable assumptions would support," the mayor said.
Johnson confirmed the price was at least twice what the city originally sold the meters for. As for which private company is buying them, the city does not know yet.
Chicago has a special talent.
it can take something as boring as a fuckin parking meter and turn it into a generational morality play.
That ain't a metaphor. W're talking about an actual metal stick on the curb that now serves as a tiny monument to civic self-harm.
Every time you feed one of these fuckking things, you are not just paying to park. You're tipping your hat to the city’s favorite past time- pawning off tomorrow to cover today, then acting shocked when tomorrow shows up with a bill, a late fee, and a boot on your car.
Peter Macdiarmid. Getty Images.Mayor Richard M. Daley lit the match with “the original deal,” a long-term privatization that traded steady public revenue for a one-time payday. Of one-billion dollars. Days before he left office. No, seriously. You can't make this up.
Like a degenerate gambler who just hit a big bet, the city (obviously) blew the cash, kept the obligations, and handed residents the privilege of paying more for less.
And now, genius Brandon Johnson, faced with the chance to change the trajectory, is either compounding the damage or proving incapable of meaningfully correcting it.
Daley made the original bad bet. And Johnson is the guy standing at the roulette table telling you the house always wins, then placing another chip anyway.
“The deal” has become Chicago shorthand for a certain kind of public failure- major decisions rushed through, long-term consequences shrugged off, and regular people left holding the bag.
In 2008, under Daley, the city entered a 75-year agreement involving roughly 36,000 parking meters for about $1.15 billion up front.
The city gave up decades of revenue and flexibility. It is the civic equivalent of selling your paycheck for the next 75 years because you found a coupon for free wings.
Meanwhile, out on the streets, the experience is simple and brutal- rates continue to go up, the hassle increases, and the resentment becomes a civic tradition. Downtown meter parking now gets cited around $7 an hour, up from about $3 an hour when the city owned them. And they are fucking everywhere now. You can't find free parking anywhere almost anywhere in this place anymore.
Daley didn’t invent short-term thinking. But he sure as hell mastered the Chicago version of it: grab the cash, spike the football, and leave the next batch of adults to wake up with the hangover. He sold “the deal” like it was some bold, forward-thinking modernization move. In reality, it was the oldest political trick in the book. Take the applause now, dump the pain later.
Because “later” is always the next guy's problem.
Chicago has perfected the art of "kicking the can". (See the city's pension debacle that nobody has addressed in 20 years).
And no, the point isn’t that privatization is automatically evil.
The point is Chicago’s version of privatization has way too often been a fire sale dressed up as reform. If you live here, you already know. We don’t get “services.” We get handed a contract you never signed and a price list you have zero say in.
The real problem with Daley’s braindead move wasn't just that it was a bad transaction, but that it has now essentially trained this city to do.
It normalized this whole governing philosophy of- if the numbers don’t work, don’t fix the system. Just sell a piece of it, kick the can, and borrow against the future.
Then stroll up to a podium and talk about “tough choices” like you’re doing everybody a favor.
(Case in point)
Fast-forward to last week. The meters are up for sale again, and City Hall was at least sniffing around the idea of buying them back. But the Johnson administration backed off, saying the asking price was too high, floating that $3 billion number, and basically warning that you’d be turning a bad deal into an even worse one once you factor in debt and risk.
On paper, that sounds responsible. “We’re not getting fleeced twice.”
"I've been looking at this deal for the last decade and a half. I know what the value is. I don't think we have the money laying around for it," said 32nd Ward Ald. Scott Waguespack.
Gee. Ya think? The city that has been broke as fuck for the last quarter century doesn't have a spare 3-billi lying around in the coffers? You don't say.
File that one under no shit Sherlock.
And here’s the part that drives me absolutely insane- saying “no” isn’t the same thing as governing.
The same reporting that mentions Johnson backing away also points out a key thing the city still controls. Any ownership transfer can require City Council approval, which means the city has at least some leverage. Couldn't you use that moment to negotiate? You can at least make some noise and throw your weight around a little. Say you've hired the best attorneys in the world to figure out a way out the deal. You can try to claw back something, anything, before the thing gets passed like a cursed family heirloom to the next private owner.
But what do we get instead? The most Chicago move imaginabl- a big loud announcement about what we’re not doing, while residents keep paying into a system everyone agrees is miserable and fucking extortionary.
(And this all lands in the middle of a bigger mess. Chicago rolled into the 2026 budget cycle staring at an estimated $1.19 billion hole in the corporate fund, with watchdogs calling it one of the largest gaps in recent history, especially now that the federal COVID-era money is drying up. Johnson’s 2026 spending plan turned into a City Council knife fight, with resistance coming from all directions)
And none of this is theoretical. It becomes all too real the first time you’re circling the block like a shark because you can’t find a spot that isn’t priced like a VIP bottle service menu.
When you’re late to something important because you spent seven minutes trying to decode the curbside nonsense. Speaking of nonsense-
In addition to the financial risks, aldermen offered other considerations.
"What if everybody's using Ubers? What if everyone's using the CTA, which would be a good thing? What if flying cars exist? What if there's another global pandemic?" said 34th Ward Ald. Bill Conway.
I don't see New York or Boston's local civic leaders coming up with big-brain points like these. Way to go Bill Conway. Way to think outside the box and look at the positives.
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Back to reality and planet Earth…
Daley’s defenders will tell you he inherited problems and needed cash and leaders have to make hard calls. But hard calls aren’t the same thing as objectively terrible calls.
Taking a one-time check for decades of public revenue and control isn’t “tough.” It’s convenient and short-term.
It’s the kind of decision that only looks smart if you already know you won’t be around when the consequences show up.
And Johnson’s defenders will say he’s dealing with a mess he didn’t create, and buying the meters back at a sky-high price would be irresponsible. Also fair and in his defense, is correct. He didn't.
The issue isn’t just the refusal, but the larger pattern around here- huge deficits, political theater, credit warnings, and way too many moments where City Hall looks reactive instead of in control, like it’s constantly trying to win the news cycle instead of actually fixing the massive cracks in the foundation.
David Greising, president and CEO of the Better Government Association, also questioned whether a change in ownership would bring a rate increase.
"We saw, when the meter deal first was let, that parking rates increased dramatically pretty much overnight, and a new owner presumably will have incentive to also try to squeeze the meters for new revenue," Greising said.
When NBC Chicago asked Johnson whether meter rates will increase under new ownership, he said: "There are some limits to what we're able to do within the confines of this deal, but as far as parking rates being raised, I think it's too early to make that projection."
= $15/hr parking in the west loop coming soon!
p.s. - you know what my favorite fucking part of these extortion machines is? The "minimum time feature". These pieces of shit are electronic and have all the bells and whistles that an Abu Dhabi backed investment fund has at its disposal. If you wanted to pay to park for 7 minutes and 31 seconds it should and would be able to accomodate you. Except that it doesn't. Nope. Why would it when it can act like it's one of the machines from last century that you needed to feed quarters to buy time. If you thought you needed an hour, but only ended up needing 5 minutes, you were out of luck, your quarters were already in the thing. Same goes with these things now. You would think that you could close out your "session" or whatever, and get your extra time you purchased credited to you or whatever right? Wrong. And the best part is they smoke you on this minimum time scam, where if you only needed 10 minutes, you still have no choice but to pay for 30 because that's the minimum they claim you have to pay for in that particular zone. It varies spot to spot, but it's totally arbitrary and total bullshit. Just another way the geniuses at city hall allowed us residents to get fucked and fleeced