Leadership Vacuum in Chicago Creates Chaos on Parking Meters

September 29, 2026

No one is in charge of the city, so chaos reigns when it comes to a simple deal involving the simplest of revenue sources: Parking meters

If you read the Chicago Tribune’s account of the chaotic process now playing out over the proposed transfer of Chicago’s infamous parking-meter concession, you may be forgiven for wondering if we actually have a mayor. By mayor, I mean not just a body warming the mayoral chair on the fifth floor of City Hall; not just somebody holding press conferences, issuing proclamations and blaming Donald Trump, billionaires, Springfield, previous administrations, or whatever other scapegoat pops into his empty head; not a mere puppet on the strings of Chicago Teachers’ Union political dominatrix Stacy Davis-Gates.

Do we have a mayor who actually runs this town? Inquiring minds want to know, because nobody seems to be running this show.

The latest parking-meter fiasco is almost a perfect case study in the incompetent dysfunction of the Johnson misadministration. The underlying transaction should be straightforward. The City Council made its original catastrophic parking-meter deal in 2008, when it foolishly leased the system to private investors for 75 years for a measly $1.15 billion after only three days of consideration. The private investors recovered their original investment in just 11 of those 75 years, by 2019, while generations of Chicago motorists were left holding the bag, paying higher meter rates and remaining responsible for compensating the sharpie buyer when spaces were taken out of service.

It has become perhaps the single most notorious municipal financial transaction in modern Chicago history, if not the global annals of municipal fiscal folly. Now the controlling interest is changing hands. New York investment firm Stonepeak Partners wants to acquire the remaining 57 years of the concession for about $2.53 billion. That requires City Council approval. Simple enough. Except this is Chicago under Brandon Johnson, where apparently nothing can be simple, except him of course.

Before Stonepeak emerged, Johnson’s administration secretly explored buying the meters back for the city. The administration made four bids, eventually offering as much as $3.2 billion. In the event that turns out to be about $700 million too much to get His Incompetence a “W” going into the election for pandering propaganda. The city then abandoned the idea after concluding that financing the purchase would expose taxpayers to enormous risk. City Hall acknowledged Chicago would have needed to borrow billions and potentially pledge parking fines, garage taxes, and other city revenue to repay the debt.

Think about that sequence. The mayor tried to commit Chicago to a multibillion-dollar transaction involving one of the most politically radioactive assets in the city behind the back of the City Council, trying to overpay by over 30 percent, making a bad deal worse for the sole purpose of saving MBJ’s political posterior at the expense of the very voters he’s trying to bamboozle. Morgan Stanley, seeing a desperate sucker, jacked up the price. Someone who learned to count in some school outside CPS pointed out to the mayor that getting taken to the cleaners by the billionaires he makes his whipping boys wouldn’t look good in the debates. Perhaps that someone was the City’s Corporation Counsel. Perhaps that’s why she walked away from MBJ. All we know is that the administration decided its own proposal was too risky and walked away.

After that, Johnson essentially handed the hot potato to the City Council. Finance Committee Chair Pat Dowell put it bluntly. The mayor had said approving or rejecting the sale was the Council’s responsibility, she explained, so aldermen “took the bull by the horns and did the work.” That may be the most revealing sentence anybody has uttered about the Johnson administration. The aldermen did the work. The “mayor,” having botched the buyout, handed the political hand grenade to the Council to dodge the blame. What an incompetent coward!

A group including Dowell, Nicole Lee, Scott Waguespack, Gilbert Villegas, and Walter Burnett, working with outgoing Corporation Counsel Mary Richardson-Lowry, negotiated concessions from Stonepeak, and they got some. Stonepeak agreed to pay Chicago $75 million upfront, earmarked for pensions so MBJ can’t throw it away on violence interrupters or some such nonsense. It agreed to give the city five percent of annual net operating income from the meters, which city officials estimate could produce up to $376 million of desperately needed revenue during the remaining 57 years of the concession. It was also agreed that if it sells the concession again, Chicago would receive another two percent of the sale price. Future transfers would also give the city a clearer review process.

Is that enough? Reasonable people can disagree. Alderman Bill Conway has argued that the much-advertised profit sharing may actually produce closer to $140 million after interest expenses and depreciation are taken into account. Alderman Jason Ervin has questioned why Chicago settled for a percentage of net rather than gross revenue. Those are legitimate questions.

However, in woke, tribal, hyper-partisan Chicago, apparently a parking-meter transaction cannot simply be about parking meters and money. Chicago politicians do what they do, which is to interject issues that have absolutely nothing to do with the business at hand to make political points with their crazy voters.

So of course we had to inject national immigration politics into it. Stonepeak owns Omni Air International, which provides long-haul deportation flights for the Department of Homeland Security. More than a dozen progressive Council members objected to that relationship, and Stonepeak agreed to sell Omni as part of the concessions surrounding the Chicago transaction. Whether they support or oppose the Trump administration’s immigration policies is beside the point. What does any of this have to do with the economics of parking meters? Chicago desperately needs money. It has staggering pension obligations and other fiscal problems. Yet even when City Hall has an opportunity to renegotiate one of the worst financial deals in its history, we somehow wind up debating the federal government’s immigration policies.  

But even that apparently wasn’t enough chaos. Having punted to the Council, our idiot mayor is now trying to sabotage the decent deal they cut AT HIS BEHEST! Johnson allies Aldermen Jason Ervin and William Hall voted against the agreement in the Finance Committee. Ervin argued the city might be able to extract more from Stonepeak and floated another attempt to regain control of the meters through a public infrastructure trust. Hall objected to what he said was inadequate participation by Black-owned businesses in the parking-meter operation and transaction, pandering to Johnson’s alienated tribal base. Hall told the Chicago Tribune that Stonepeak currently was not doing business with African-American firms and argued that was unacceptable in a city that is 27 percent Black.

So now we have reached the full Brandon Johnson City Hall experience. The mayor secretly tries to buy the meters. He abandons the effort and tells the City Council that the decision is theirs. Council members negotiate their own compromise. The mayor’s own Corporation Counsel participates in negotiating it. Progressive council members force an unrelated immigration-policy concession into the agreement. The Finance Committee approves it. Then aldermen allied with the mayor work against it for entirely different reasons, and the full City Council punts the vote. All of this is happening against a September 30th deadline, after which Chicago risks arbitration and litigation if the Council refuses to approve the transfer. The Council is now scheduled to take the issue up again Tuesday, September 29.

Who, exactly, is in charge? That is the issue here. You can support the Stonepeak deal. You can oppose it. You can believe the aldermen extracted enough concessions, or you can believe they should demand more. You can even argue that Chicago should someday find a financially responsible way to regain control of the parking meters. Those are policy disagreements. But you can’t support this kind of sneaky, vacillating, backstabbing,  gutless abdication of leadership. A functional mayor should have decided what his administration believed was in the city’s best interest, assembled his financial and legal advisers, consulted the City Council, developed a strategy, and then attempted to execute it. Instead, we have City Hall going in six directions simultaneously. This clown talks out of both sides of his mouth, and neither side makes any sense.

No one personifies the problem better than departing Corporation Counsel Mary Richardson-Lowry. The city’s chief lawyer presumably represents the administration. She participated in negotiating the Stonepeak compromise and defended it before aldermen, pointing out that the agreement would provide Chicago with revenue it never had under the original contract. She is also leaving the administration. Watching all of this, you can understand why. Chicago has always had political warfare. Richard J. Daley practically invented modern machine politics. Harold Washington battled the Council Wars. Richard M. Daley exercised enormous power. Rahm Emanuel certainly never suffered from an inability to make his position known. Lori Lightfoot fought with practically everybody in the building. But at least you knew who was in charge.

With Brandon Johnson, City Hall increasingly resembles a collection of competing political tribes with nothing in common except City Hall offices, competing factions of pirates aboard a rudderless, sinking ship. It’s every man for himself, the passengers be damned. One is reminded of Joseph Conrad’s classic novel Lord Jim. At least in that fictional depiction, the protagonist was plagued by guilt and shame. Our Lord Mayor has no shame; all he has for the hapless passengers of his sinking ship of state is contempt, condescension, resentment, and blame. He fiddles the race card blues as we drown in a stormy sea of red ink and strive to survive amidst crime, filth, and squalor. That’s an existential threat for a city facing literally existential problems.

The parking meters themselves are ultimately just one chapter in the litany of disaster this so-called mayor has left as his legacy, only one episode in the havoc he has wreaked on this once great city. The overarching issue is whether Chicago has an executive branch capable of making decisions, coordinating policy and, most importantly, leading for the benefit of all Chicagoans, not just those who belong to one union or one tribe. On the evidence of this episode, the inarguable verdict is "No."

Chicago cannot afford government by improvisation, deception, division, and dissembling. It cannot afford to turn every financial transaction into another battlefield in the ideological wars consuming City Hall. And it certainly cannot afford another four years in which nobody seems quite sure who is running the city. The 2008 parking meter deal should have taught Chicago an enduring lesson about municipal government: Competence matters. The next mayoral election gives voters another opportunity to apply that lesson. They can examine Johnson’s credentials, or rather lack of same, alongside those of his challengers and decide whether his administration has demonstrated the financial judgment, executive discipline and leadership they want for another term. One thing is clear: MBJ has proven beyond the shadow of a doubt that he is incapable of doing the job.

Chicagoans made a similar judgment four years ago when they rejected Lori Lightfoot. Whoever voters choose next, they should scrutinize something more important than ideology, identity, slogans, or coalition politics. They should ask whether the candidate can actually run the government, because Chicago needs a mayor capable of imposing order on City Hall, articulating a coherent vision and getting 50 aldermen, city departments, business interests, unions, and neighborhood constituencies moving in the right direction.

The parking meter circus demonstrates what happens when clowns are elected instead of Caesars. Chicago deserves better than government by chaos, and before this city is torn apart by its fiscal problems and increasingly tribal politics, voters should demand it.

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