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player ready...I wish my parents had told me when I was young that adulthood would be broadly miserable. I don’t mean marriage, family, career, maladies, or politics (though I assure you we’ll get to that last one). I’m referring to the slights, inconveniences, and small injustices that accumulate into the persistent, annoying, and unavoidable frustrations you encounter in day-to-day life. You know, potholes, paper straws, everything about air travel. But once in a while, human ingenuity will chip away at this daunting bedrock of built-up angst, because one of the miracles of mankind is how a single person’s imagination can shatter a powerful, overly restrictive force.
This is what I thought last summer when someone told me, “You know, I have a friend who doesn’t pay for parking in Chicago.”
“What do you mean?” I asked, lightly choking on a sip of water.
If you live in Chicago — and perhaps even if you don’t — you know the psychic weight street parking holds over the populace here. That’s primarily because Chicago doesn’t control the vast majority of metered spaces within city limits. Back in 2008, Mayor Richard M. Daley and the City Council infamously agreed to sign over rights to roughly 36,000 meters to a group of investors, led by Morgan Stanley Infrastructure Partners, for 75 years in return for $1.16 billion.
That might sound like a windfall for the city, but in hindsight, Chicago got played. With 57 years remaining on the contract, that consortium, which is now in the midst of trying to sell the lease to another party, has, in terms of gross revenue, already gotten a return of nearly twice its investment. For most Chicagoans, the parking meter deal epitomizes all of the city’s most exhausted pejoratives: shady backroom handshakes, cartoonishly inept politicians, widespread institutional dysfunction.
That was how Chester, a 33-year-old Northwest Side resident, thought about it. As our intermediary relayed it to me, Chester (that’s an alias) had to drive to his office every weekday, and metered street parking was the only option. Exasperated by the cost, Chester began to look for flaws in the system that he could exploit. He noticed that enforcement was spotty around where he worked, and as a self-described “politics and urban transit nerd,” he knew enough details of the meter deal to have a cursory understanding of how the money flows.
While the group that owns the lease collects all the money from meter payments, the revenue generated by ticketing goes to the city. Chester speculated that if he stopped feeding the meters entirely and paid his tickets on time, not only would all the money he spent go to the city, but he would actually end up paying less overall.
“We all gamble with it a little around the city, right?” Chester tells me when we meet up. “And I started gambling with it, because it was just like, Man, I can’t pay this every single day. Eventually I did the math, and I was like, Screw this.”
This was approximately two years ago. Whole weeks would go by without Chester getting a single ticket. When a parking enforcement agent would slap an orange envelope on his car, he would make sure to pay up on time. At one point, he thought the enforcement folks had gotten wise to him. Two days in a row, he found a ticket on his windshield. “All the tickets only came in the morning, at 9 a.m., and so I started paying the meter for the first hour and then I didn’t pay for the rest of the day.” Eventually he stopped entirely, and things went back to normal, which meant an average of slightly less than two tickets a month.
Chester speculated that if he stopped feeding the meters entirely and paid his tickets on time, not only would all the money he spent go to the city, but he would actually end up paying less overall.
I ask Chester to do some back-of-the-napkin math. After a couple of minutes, he determines, conservatively, that he’s saved $1,500 over the past two years.
For someone who conceived such a shrewd workaround to such a colossal civic boondoggle, Chester isn’t especially sophisticated or debonair. He wears ordinary round glasses, and his face is entwined by a brambly beard. By day, he works as a digital product designer, and he’s not even from Chicago originally (he moved here from New Jersey). He has an impish demeanor and punctuates his accounts of his parking adventures with self-satisfied chuckles. In fact, for a self-described “politics nerd,” his command of city politics is questionable. He tells me, “Daley sold off the parking rights to JPMorgan Chase.” (Not true.) “I think all of it’s owned by, you know, a bunch of Saudi oil trusts, or whatever.” (It’s not.)
If Chester is doing this on principle, it’s a sketchy one. He freely admits that he pays for parking in largely commercial areas like in Lincoln Park or on major business corridors like Milwaukee Avenue, because he’s certain the enforcement is more stringent there. He describes what he’s doing as “a minor form of rebellion.” He calls himself “a lazy activist.”
But Chester belongs in the pantheon of great Chicagoans, up there with Harry Caray and the Tamale Guy. Like those heroes, he’s exposed a flaw in an established order, birthing new possibilities for the local populace. What would happen if we all followed Chester’s lead? Could we rise up as Chicagoans and stop paying the meters? Maybe the way for Chicagoans to get their parking spots back is to deploy the one weapon at their disposal: a strike.
Is the Chicago parking meter deal the worst municipal finance contract in history? You’ll certainly find people who feel that way. Alderperson Scott Waguespack of the 32nd Ward — one of five City Council members who voted against the arrangement in 2008 — declared it as such as recently as last December, when he appeared on an episode of NPR’s Planet Money. (When I ask him if he still feels that way, he hedges slightly: “For Chicago, yeah.”)
Justin Marlowe, director of the Center for Municipal Finance at the University of Chicago and a close observer of the deal, doesn’t like to speak in absolutes. But he will say: “Empirically, it’s difficult to find another public-private partnership or another privatization anywhere in the country, and perhaps even anywhere in the world, where the government entity appears to have left as much taxpayer money on the table as Chicago left.”
One of the curious aspects of the parking meter deal is that everyone’s understanding of it is colored by their anger toward it, as Chester demonstrates. You might hear that the meters are owned by the government of Abu Dhabi (said to me by a friend), or that parking downtown is $9 an hour (said to me by a relative), or that the city doesn’t pocket any of the ticket revenue for meter violations (said to me by someone who works in City Hall). None of those things are true, or they’re partial truths.
The Abu Dhabi Investment Authority, which invests on behalf of that Arab emirate’s government, makes up nearly half of Deeside Investments. Deeside, in which German financial company Allianz has an indirect majority stake, in turn owns just less than half of the meter lease. (The rest is controlled by Morgan Stanley.) The current hourly rate in the Loop is $7 an hour. And all parking infraction revenue, including for meter violations, goes into local government coffers.
“It’s difficult to find another public-private partnership or another privatization anywhere in the country where the government entity appears to have left as much taxpayer money on the table as Chicago left.”
It’s nearly impossible to understand the parking meter lease deal without understanding the rationale behind it. The date it was approved is important: December 4, 2008, three months after the biggest financial crisis since the Great Depression. Chicago was desperately strapped for cash amid a looming budget crunch that could have torpedoed the city’s finances, so it put the meters up for bid. “People go into this discussion about the parking meter deal with this idea that everybody kind of conspired to bilk taxpayers out of a lot of money,” Marlowe says. “That’s not what happened. What happened was the City Council had no leverage and very limited options for how to close a big budget gap. This was one that appeared.”
But how did the deal wind up so one-sided? As Marlowe explains, Morgan Stanley was able to conduct much more sophisticated data analysis than the city regarding how much could be made off Chicago’s meters over time. More importantly, Morgan Stanley was aware of both that information asymmetry and the city’s financially stressful position. “At a very high level, what I always like to tell people is the parking meter deal accomplished its main goal, which was to close a gap in the city’s budget for that year,” Marlowe says. “And as a public policy and public finance guy, that’s our first question: What was this intended to do and did it do it? In that sense, the answer is yes.”
There were also precedents for the privatization of local public assets. In 2005, the city leased the Chicago Skyway toll road to an investment group for 99 years at a price tag of $1.83 billion; the following year, it granted a 99-year lease on four downtown underground parking garages for $563 million. Few people complained about either deal. The initial press was overwhelmingly favorable, with a baiduhai headline declaring the Skyway deal a “jackpot” for the city. The majority of Chicagoans didn’t seem to mind that their local government no longer controlled these assets.
Dana Levenson was the city’s chief financial officer from 2004 to 2007 and played a central role in the Skyway and downtown garage leases. Though he left that position before any aspect of the parking meter deal was negotiated, I reached out to him after Marlowe told me that Levenson defends it to this day. And he does, vehemently. “Chicago was feeling the effects of the Great Recession in terms of its economically sensitive taxes going down, including the hotel tax and the gas tax,” Levenson says in a yawning Massachusetts accent. “On the heels of the Skyway deal, the city’s debt ratings got raised to the highest they’d ever been.” Levenson remains mystified that Chicagoans make such a stink about the meters but rarely complain about either of the two infrastructure leases he helped engineer.
He’s quick to remind me what the old parking meters were like: They were a pain. The giant gray inverted pears, affixed to metal poles growing out of the ground in tightly spaced intervals, were obstructive to pedestrians. And if you happened to be somewhere longer than you’d planned, you’d have to walk back to your car for more quarters to feed the meter. (All through my childhood, my parents kept large ziplock bags filled with coins in their cars for this purpose.) In short, the city had clunky and outdated parking technology and no money to update it.
Another challenge was an obstinate City Council that refused to raise the rates for street parking, fearful of the political blowback that would ensue. (At the time, the rate was $3 an hour in the Loop and as little as 25 cents elsewhere.) So Chicago was locked into a limited, aging revenue stream.
Levenson believes the antipathy toward the deal stems from how poorly it was initially handled by Chicago Parking Meters, the company established by the investors to manage the meters and act as their local go-between. When it took over the meters in February 2009, it had the city increase the rates immediately, before CPM could upgrade the technology. Drivers were now shoving ludicrous fistfuls of quarters into old meters. Predictably, people rioted, albeit nonviolently, smearing goo on the meters, putting putty into the coin slots, and spray-painting the display windows.
But how has CPM done in the 17 years since? It isn’t unreasonable to argue, as Levenson does, that the company is doing an exemplary job. Even Waguespack agrees, telling me, “They are operating it very well.” We have a parking system that is fully digitized and intuitive and rarely malfunctions. Though the current parking rates — from $2.50 an hour in noncommercial areas to the Loop’s $7 an hour — are some of the highest in the nation, comparable to those in New York City, prices have gone up everywhere in the country. And LAZ Parking, the company CPM contracted with for meter enforcement, provides Chicagoans jobs without taxpayers footing the bill.
When the city turned to privatization to solve budget shortfalls, it was also freed from having to concern itself with the infrastructure. Municipal officials didn’t have to worry when a meter broke down. They didn’t have to get chewed out when they raised parking rates. Look at the aging Skyway: Officials didn’t have to fret over maintaining it.
It’s true that much of the $1.16 billion the city received in the parking deal went to addressing the fallout of the financial crisis. But $400 million went into long-term reserves to help replace the future lost revenue, just as $500 million from the Skyway deal had, and $326 million went into a budget-stabilization account meant to help the city bridge the gap before the economy picked back up. “If Chicago didn’t have that rainy day fund, its bond ratings, which stink, would be a hell of a lot worse,” Levenson points out. “We would be solidly in junk bond territory.”
The rationale Levenson outlined made sense to me. What was happening? Was I turning into a rube? I’d worked at the Chicago Reader, which in 2009 published Mick Dumke and Ben Joravsky’s investigative series on the meter deal, titled “Fail.” I occasionally edited Joravsky, who was mostly allergic to email. He’d call, sometimes when it was incredibly inconvenient, to argue about headline choices, workplace minutiae, or even Quentin Tarantino movies. So now, at 3 a.m., I woke up in a sweat and dove for my phone, afraid he really had called to yell at me for going to the dark side. I could almost hear his sardonic Chicago drawl: “Tal, how did you let these guys get to you?!”
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As I was looking into the details of the original deal, Chester’s no-parking policy was continuing apace, and other people were getting in on it too. I told a close friend of mine about the hack. “That’s genius,” he said. The next day, he stopped paying for street parking at his Far North Side job. He went more than a month before he got an orange envelope. I advised him to go back to paying for a week, then resume nonpayment. He hasn’t received a parking ticket since, and that was three months ago.
Often when I mention Chester’s gambit to other Chicagoans, they admit to doing a less methodical version of it — not paying for parking in certain parts of the city. Clearly, enforcement is happening: I’ve seen tickets being issued. So why were the meter-ignoring parkers I talked to getting ticketed so infrequently? In the early 2010s, if I ever tried to sneak in a quick errand without paying the 15-minute meter minimum, a ticket would appear near instantaneously on my windshield. Had something changed? I attempted to find out, which required some digging with the city and CPM.
First, some info on who’s who: If you see a ticketer wearing a neon yellow-and-orange vest, chances are they’re a city employee. They work in the Department of Finance and issue tickets for meter and other violations — expired city stickers, parking in front of a fire hydrant or during restricted hours, and so on. (Chicago police officers also have the power to give out tickets.) But the ones in green vests? They are LAZ employees.
In April, I tried to contact a Department of Finance representative by phone; I was passed around to a couple of operators and eventually transferred to voicemail, but it was full and I couldn’t leave a message. Afterward, I emailed the city’s press office to request information about how parking is enforced. A representative from the mayor’s office replied and said they would follow up, but I’ve yet to hear back. I filed a Freedom of Information Act request with the city, asking for enforcement specifics. The Department of Finance denied it, arguing, among other things, that releasing scheduling details could put enforcement workers in danger and cause “competitive harm” to CPM. The department also balked at revealing “operational enforcement patterns that may be exploited to avoid compliance, thereby undermining the effectiveness of the program.” Apparently, the city was onto the Chesters of the world.
As for CPM, it lists no contact phone number on its website. However, a Google search showed it has an office at 205 North Michigan Avenue. So on a Monday morning in early May, two weeks before it was announced that CPM had come to terms on selling the lease, I went down there. I didn’t get past the front desk. The kind receptionist handed the phone to me, and I told the woman on the line that I was trying to find someone who could provide details about parking enforcement in Chicago. The woman gave me her name, but told me I couldn’t print it, and said that CPM would not be speaking to the press. Then she hung up.
My visit to CPM, though, did clarify something obvious about the very nature of privatization, which is that it excludes the public. CPM isn’t held to the same transparency standards or scrutiny as the city, even though it manages public infrastructure. A major cause of the animosity toward the parking meter deal was the rushed manner in which it was enacted. The City Council had only about 24 hours to review the 500-plus-page lease agreement before it was brought to a vote.
Had the public known the full extent of the deal, it would have surely objected to one aspect in particular: “true-ups.” These are payments the city makes to the leaseholder to compensate it for lost revenue whenever meters are taken out of commission, like for construction or street festivals. And if the meters are retired permanently — say, a street is redesigned to add an express bus lane — the city has to continue to make these payments quarterly over the remainder of the lease term: currently, 57 years. Levenson argues that the city would have lost out on the revenue from those out-of-commission meters anyway, even if it had retained control of them. Still, the added insult of making payouts on top of getting bested in a deal stings.
When the city sold off the meters, it also ceded some control of our streets. I can’t help but riff on the scene from Goodfellas when Paulie Cicero is brought in to help manage a restaurant. Want to have a new street fair in Logan Square? Eff you, pay me! Want to temporarily remove a parking space to put a dumpster in for a construction project? Eff you, pay me! Want to turn Milwaukee Avenue into a no-car zone on weekends? Eff you, pay me! If CPM disagrees with the amount that the city estimates for the true-up payments, it can file for arbitration.
In May, policy analyst and transit advocate Nik Hunder offered a potential response to true-ups. In an article for the A City That Works newsletter titled “Let’s Move Some Parking Meters,” he posits that the city could reposition meters and adjust rates, within the boundaries of the contract, in such a way as to avoid true-up payments entirely. Though the City Council often uses this tactic to reduce payment amounts, Hunder contends that it could be even more aggressive in doing so. But this can get tricky, Waguespack points out. Widespread parking meter reallocation requires coordination between City Council members from different wards. “Not all aldermen do that,” he says of council members relocating decommissioned meters. “A lot of them ignore it, and that’s where the true-up really hits you.”
The investment consortium that leased the meters appears to be bearish on their future. It’s easy to infer why. For one, the pandemic fundamentally changed the nature of work.
The city has tried even more creative measures, including a dubious one, to finesse the terms of the true-up. In November 2021, amid COVID, it retook control of just over 4,000 parking spaces. Because the pandemic had temporarily depressed the revenue value of these parking spaces, the city calculated the true-up payment as around just $10 million. Two months later, when the value was recalculated based on rebounding 2021 parking revenues, the city returned 2,646 of those spaces to CPM for a $13.8 million credit — flipping them for a $3.8 million profit while retaining 1,361 spaces.
After CPM objected, an independent arbitrator ruled that the Lightfoot administration had violated the contract by devising what was essentially an arbitrage play. The city’s own appraiser estimated the move would cost CPM $120.7 million over the life of the lease, though CPM argued the amount was much higher.
CPM, citing this and other maneuvers by Mayor Lori Lightfoot’s administration, took the city to court, demanding $322 million. Eventually, in May 2025, the city negotiated a settlement to pay CPM $25.2 million, including legal fees, while keeping the $26.2 million in revenue it had generated from the spaces. It was a much better outcome than had been feared. At the time, Waguespack told the Chicago Sun-Times, “This is our first win in a series of losses on this deal — and it still doesn’t feel like a win.”
But in some ways, the settlement made the lease even worse for the city. The arbitrator had effectively prioritized CPM’s interpretation of the contract, setting a precedent for future disputes. “I was like, Jeez, even the pandemic couldn’t break this thing,” says Waguespack. “This contract is rock solid.”
So then why has CPM put this cash cow up for sale? To answer that, you have to dig below the surface. The public perception is that the consortium behind CPM still has 57 years of reaping meter revenues over and above the relatively paltry sum it paid. But that is based on a misunderstanding of where the money we pour into meters ends up. In the case of Morgan Stanley and Allianz, the meters are one investment among many, which have been aggregated into private funds that a variety of groups invest in. As Levenson points out, it would not be impossible that one of Chicago’s municipal pension funds, like that of the police or the firefighters, has money in a Morgan Stanley infrastructure fund that has a stake in the parking meter lease.
Given its sophisticated technology to determine the long-term trajectory of its investments, the consortium behind CPM appears to be bearish on the future of the meters. It’s easy to infer why. For one, the pandemic fundamentally changed the nature of work, and while the Loop and its surrounding neighborhoods were once predictably the places to pull in the bulk of meter revenue, with so many commercial vacancies there — not to mention more parking alternatives through services like SpotHero — that’s no longer a guarantee. And if Waymo’s self-driving cars are allowed here and prove to be as popular as they are in California, then we can expect the need for parking spaces to decrease even further.
Also, CPM had to take on debt to pay for the installation of our modern parking system and for LAZ to operate it. A 2018 report by Fitch Ratings issued CPM a BBB− rating, one step above junk level, arguing that because of technological shifts, parking revenue was projected to decline just as CPM’s debt payments would begin to escalate. “There’s a cost to CPM when it comes to calculating the ultimate return,” Levenson says. “There’s interest that is being paid back on that principal. Did CPM make back their money in a relatively short amount of time compared to the length of the lease? Yeah, they probably did. That doesn’t necessarily mean the annual return on investment is meeting the criteria that [CPM] set out for itself.”
Even the city decided that it didn’t make financial sense to buy back the meters. In January, ABC-7 reported that Mayor Brandon Johnson’s administration had made a bid as high as $3.2 billion before backing out. Ultimately, Johnson’s team determined that most of the revenue gained from the meters over time would go just toward paying off the debt from buying out the lease.
Last December, CPM wound up agreeing to sell the meters to Stonepeak Partners, a New York City private equity firm, for $2.53 billion — significantly less than the city offered. If Fitch Ratings anticipates that meter revenue will decline, why would Stonepeak swoop in? Waguespack explains that the meters are still profitable and Stonepeak doesn’t have to take on as much debt as CPM did to lease them. “Stonepeak could ride it out for another 10 to 15 years and still make money,” he says. “These guys basically just have to pay to manage the asset now.” Down the road, Stonepeak could unload the lease, just as CPM is trying to do.
That’s why Marlowe thinks the city might eventually have another opportunity to slide out from under this deal. In fact, in an opinion piece in the Tribune in mid-July, 28th Ward Alderperson Jason Ervin floated the idea of Chicago creating a public infrastructure trust to try to buy back the meters. Says Marlowe: “There might be a scenario where the city is willing to pay a slight premium relative to their private potential because it is valuable to feel as though we have reclaimed control of the curb. And it is valuable to feel like we are no longer beholden to this contract that makes us feel as though we don’t control our public spaces and so forth. How long that will take, and how much we should be willing to pay for that — those are interesting questions.”
Some frustrated Chicagoans don’t want to wait. For now, their only recourse is to go to court. One man has already tried that.
Thomas Geoghegan sits in his office with his eyes shut tight, pressing his long, thin index and middle fingers against his temples. At 77, he has to think hard before he can remember specific events or facts. But you also get the sense that for him, contemplating the parking meter deal is excruciating. When he first heard about it, he recalls, “I thought it was a monstrosity.”
In progressive circles, Geoghegan is a minor celebrity. He’s a labor lawyer and prolific writer (he’s the author of eight books and a former staff writer for The New Republic) who ran for the congressional seat Rahm Emanuel vacated in 2009 (he finished seventh in the Democratic primary). Micah Uetricht, the editor of the left-wing magazine Jacobin, tells me that it is a Chicago badge of honor to have your name attached to a Geoghegan-prepared lawsuit. In his case, it was the class action Uetricht v. Chicago Parking Meters LLC.
Shortly after the meter deal took effect in 2009, Geoghegan contacted the Better Government Association, a nonpartisan watchdog organization, hoping to build a case against CPM. It passed but connected him with Clint Krislov, an attorney who was in the midst of preparing a lawsuit of his own against CPM. Krislov, who died in 2024, believed that the city had spent public money on something that didn’t serve a legitimate public purpose. “I wasn’t particularly interested in bringing that claim,” Geoghegan says. “I didn’t think it was all that likely to prevail, but he very generously said, ‘Well, bring your claim as count 2.’ ” Geoghegan’s claim was that by putting limitations on the removal of parking spaces, the contract violated the city’s police power, its fundamental authority to govern its own streets.
Yet when the case went before the Circuit Court of Cook County, the city chose to defend the arrangement alongside CPM, even after Emanuel, who had initially publicly criticized the deal, succeeded Daley as mayor. Geoghegan and Krislov lost their case.
Undeterred, Geoghegan decided to challenge the deal on the federal level. He started looking into antitrust law. At Harvard Law School, he had studied the subject under Stephen Breyer, who later served as a Supreme Court justice. Geoghegan filed a new suit against CPM in the U.S. District Court for the Northern District of Illinois in June 2021, attaching Uetricht’s name and those of two others as the plaintiffs and citing the Sherman Antitrust Act, which prohibits monopolistic business practices. “CPM had an idea of what kind of legal challenge would be brought, and they drafted [the deal] to address that,” Geoghegan says. “They didn’t anticipate the Sherman Act. They were caught off guard.”
Nonetheless, the court ruled against Geoghegan. He took his case to the U.S. Court of Appeals for the Seventh Circuit, where CPM’s lawyers invoked a state statute originally designed to regulate municipal parking garages and lots to convince the court that there was no antitrust violation. A final appeal to the U.S. Supreme Court went nowhere — it declined to take the case.
“Imagine if the deal had gone into effect in 1890 for 75 years and required stalls for horses up and down the streets of Chicago. How many agreements exist like that? Zero.”
Throughout his attempts to void CPM’s contract, Geoghegan was most dismayed by local government officials. No mayoral administration — not Emanuel’s, not Lightfoot’s, not Johnson’s — would join him in the fight. But in fairness to City Hall, it might have seen Geoghegan’s legal case as far-fetched. Julie Roin, a UChicago law professor who specializes in state and local finance law, has written about the parking meter lease and doesn’t find Geoghegan’s arguments convincing. “The parking meter deal was an abomination on many, many levels,” she says. “But I don’t think it was illegal in any sense. It was just stupid.”
Particularly stupid, in Geoghegan’s view, was the 75-year term of the lease. “Imagine if the deal had gone into effect in 1890 for 75 years and required stalls for horses up and down the streets of Chicago,” he says. “How many agreements exist like that? Zero. They used to be knocked down by courts a century ago for having excessive terms.”
When it comes to escaping the contract, Roin thinks it’s hopeless. “I knew from the first instance that there was no way out of it.”
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There is, in fact, a way, but it’s extreme. Marlowe calls it “public finance science fiction” — municipalities can’t declare bankruptcy under Illinois law — but he raises the possibility that the state could pass legislation that would allow the city to file for Chapter 9 protection. “There’s people who think that bankruptcy is the only way forward on pension liabilities, and the added benefit is the city could at that point tear up the parking meter deal,” he says.
When I mention this option to Roin, she counters that it would create chaos: “There would probably be strikes by city employees. There would be huge fees paid to bankruptcy lawyers to work out a new deal.” She smiles. “Let me be clear: I think the City of Chicago is bankrupt.”
The city still has some power over the lease: The sale to Stonepeak requires City Council approval. But Levenson is skeptical that the council could leverage that to negotiate significantly better terms. “Let’s play it out,” he says. “The city says, ‘Well, we’ll approve it, but only if you put in the deal that the new owner has to reduce the price of parking.’ Morgan Stanley would say, ‘See you in court.’ And I think they would probably win that case, because it would be saying that Chicago is being unreasonably unaccommodating.”
Waguespack points out that the contract as written allows CPM to sell the lease without having to subject it to renegotiation. Which is why some on the City Council have been looking for ways in which LAZ might have breached the contract, like by claiming it has not met its requirements for hiring minorities. But Waguespack, who understands the contract perhaps better than anyone else on the City Council, thinks LAZ has been in compliance on that front. One area where there might be some leverage, though: In June, 15 council members signed a letter expressing concern that Stonepeak owns a charter airline that operates deportation flights for U.S. Immigration and Customs Enforcement.
The biggest problem, Waguespack feels, is that the mayor’s office didn’t give the council enough of a runway to maximize its leverage. When the mayor’s office made a bid, it signed a nondisclosure agreement with CPM. So most alders were not briefed about the deal with Stonepeak until mid-May. This meant the council had only about a month and a half to deliberate on the lease transfer before the June 30 deadline to vote on it — a deadline that was subsequently pushed back to September 30. As Waguespack recounts: “The mayor’s staff came in with the finance director, and we started asking basic questions. ‘When did the clock start?’ ‘The clock started about 50 days ago.’ ” At that point, the alders weren’t even given the purchase price or told the amount that the city had bid. “We didn’t know about [the NDA] except from reading it in the newspaper. No information was shared, and they control all the information. The mayor’s office controls the Finance Department. We’re like, ‘But you represent us.’ ”
He thinks the City Council’s best hope is to extract some tweaks to terms from Stonepeak, like making rate adjustments by implementing dynamic pricing. It’s all about how gently the council can squeeze the prospective new leaseholder before it could argue that the city is illegally holding up the deal. “We don’t want to drag this out for months and months, because they could easily say we’ve already gone well past the deadline and it’s not their problem,” Waguespack says. “It’s not like we can keep invoking different mechanisms to drag it out. They have a right to sue if they want, which I don’t think they want to do. I think they want to give us just enough time.”
Where does that leave us Chicagoans? Do we need a revolt, a refusal to pay for parking the way Chester does, but on a mass level? Roin points out that not everyone has the financial means to pay off parking tickets if they stack up. “And if you don’t pay the tickets as they arise, your car can get booted,” she adds. “You lose possession of your car.”
She also alludes to the very nature of true-up payments: If the leaseholder feels the city’s parking enforcement isn’t sufficient to get drivers to pay the meters, it can demand the expected revenue from the city. In isolated cases like Chester’s, that would be difficult to prove, but it wouldn’t be if the whole city suddenly stopped paying.
Seven months after my first conversation with Chester, I follow up with him to share what I’ve learned. He works at his office just two days a week now, but that hasn’t changed his approach to street parking. He says he is getting about one ticket every other month now, and the math is still in his favor. During our first discussion, I was thrilled by Chester’s parking hack, and we laughed about it. This time, I am a little downbeat. I tell Chester that after looking into it, I discovered that ignoring the meters en masse could ultimately have consequences for taxpayers.
Chester’s playful demeanor dissolves. He stares at the floor as if he’s never considered this possibility. I ask if knowing this changes anything. “It changes how loud I might have this conversation with other people,” he says, slowing his cadence. “In the short term, it is doing the two things I want, which is that if I’m going to pay the city for parking, I should pay the city for parking. And I also like to save money. It is succeeding at those two things. Do I want everyone in the city to start doing this? That’s a hard thing to answer.”
There is a long pause. “I don’t know if I’m always the best long-term thinker. It took me a very long time to quit smoking.”
I tell him not to worry about it. Municipal finance is complex, and understanding the nature of these contracts is hard. At that point, Chester exclaims, “And it’s just growing more complicated, as is American capitalism! Look at the prices of Divvy over the last five years! Or the fact that Ventra didn’t follow up on half of its promises of low-cost banking for people in the city. So many of the times we turn to private entities to take over for these things, it feels like the people just end up with the short end of the stick.”
“An asset like Midway is perfect for a privatization. But the attitude, the underlying politics of it, are just so soured, understandably, that it closes off a valuable line of conversation at a time when, frankly, Chicago is going to need a lot of financial innovation.”
I remember something Marlowe told me: He isn’t against privatization, and to him, one of the worst aspects of the parking meter fiasco is how it made public-private partnerships so reviled in the city. “Think about something like Midway,” he said, referring to a 2008 deal to lease the airport to a consortium of investors, led by Citigroup. That group eventually backed out because of the recession. “Maybe back then that deal may not have been the best deal for the city. But an asset like Midway is perfect for a privatization. You could make the claim that a private-sector operator could go in there and provide a much better service than the city’s Department of Aviation currently provides and generate way more revenue. If you’ve been to the new terminal in LaGuardia Airport, for instance, that was done through a public-private partnership. Think about the lead service line problem that we have within our drinking water system. That’s ripe for private capital to come in and shake things up. But the attitude, the underlying politics of it, are just so soured, understandably, that I think it closes off a valuable line of conversation at a time when, frankly, Chicago is going to need a lot of financial innovation to be able to get through some of our immediate budget challenges.”
Except it’s just not the underlying politics. It’s politics, period. It was politics that got us into the parking meter deal. Marlowe might be correct that privatization can be good for Chicago. But would you trust Chicago politicians to make those arrangements responsibly? After all, when the city government was faced with a historic financial downturn and a major budget crisis, the parking meter deal was the best solution it could come up with.
Throughout my life in Chicago, the city has been beset by budgetary problems and fiscal mismanagement. And at virtually every turn, it’s everyday Chicagoans who are weighed down by them. The costs might seem overwhelming, like there’s nothing we can do to reduce them. If you feel that way, let me make a small suggestion to ease your troubles: The next time you park a car on a metered street, consider not paying. But don’t tell anyone. It will be our secret.
Tal Rosenberg is a freelance writer for Chicago magazine.