Every time a Chicagoan shells out money to drive on the Skyway, park on the metered streets of Chicago, or park downtown in a public garage like the Millennium Park Garage, keep in mind that those dollars go to outside investors, not the city.
As Chicago undergoes the 2025 budget season, hunting for creative ways to close a nearly $1 billion gap shortfall, memories of former Mayor Richard M. Daley privatizing the city’s profitable assets haunts City Hall, especially the 2008 parking meters deal.
“I wasn’t in on the negotiation,” Ald. Emma Mitts (37th Ward) told The TRiiBE about the parking meters. She was one of the 40 alders who voted in favor of the deal. At the time, she had been in office for eight years.
Today, Mitts and other alderpersons in the Chicago Aldermanic Black Caucus, who also voted for Daley’s deal back then, admit that the deal wasn’t smart but some also say it would’ve done little to solve the city’s current financial crisis. The deal, now 16 years old, has been widely criticized as being one of the most foolish deals in Chicago’s history.
It passed almost unanimously by the City Council in a 40-5 vote back then. Five alders missed the vote, according to the Chicago Tribune: Sandi Jackson (7th Ward), George Cardenas (12th Ward), Isaac Carothers (29th Ward) Ariel Reboyras (30th Ward), Helen Shiller (46th Ward).
“So it was a bad deal and it was a mistake made, and now we’re living to regret it,” Mitts continued. “Charge it up to lack of experience.”
City Council’s unanimous shutdown of Mayor Brandon Johnson’s proposed $300 million property tax hike at a special meeting on Nov. 14 carries remnants of the financial trauma and distrust left behind after Daley’s trail of privatization. On various occasions, Johnson has touched on the city having no other revenue-generating assets. In 2005, Daley leased the Chicago Skyway for 99 years to Skyway Concession Company, LLC for $1.83 billion. The deal marked the first time an existing toll road was privatized in the country.
In 2002, the Daley administration also leased off the city’s “street furniture,” or bus stop shelters, to JCDecaux Chicago LLC. In the deal, the company has to maintain the bus stop shelters and gets to advertise for free on such structures. Former Mayor Rahm Emanuel reached a billboard agreement with JCDecaux, an international outdoor display company, in 2012 for a guarantee of $155 million over the next 20 years, further leasing off public assets. Chicago has long been considered a leader in privatization efforts by cities.
Daley inked the infamous 2008 parking meter deal to avoid property tax hikes and look more favorable to taxpayers. But it was a short-sighted return investment. Daley received a one-time payment of a little more than $1 billion by leasing the parking meters to private investors for 75 years. The investment company that owns a large stake in the parking meters is based overseas in Abu Dhabi, the capital of the United Arab Emirates. At the time, the Chicago Reader wrote, “Eventually the private company will make a fortune off the deal—but by then everyone now running the city will be gone.”
Today, of the 40 alders who favored the deal, only seven remain in City Council.
Damon Jones, economist and associate director at the Harris School of Public Policy at the University of Chicago, described the parking meter deal as “a wash.”
“In the long run, when you sell an asset like that for the City, and you get cash today, it’s kind of an illusion. Today, you look like you’ve increased your finances, but in the long run, you foregone a lot of future revenue,” Jones said.
Jones couldn’t say if Chicago would be in a better place financially if the deal wasn’t made but he said the deal highly favored the investors, with the city getting the very short end of the stick.
“If this company has already made back their money in 15 years, over a 75-year deal, that tells you that that company got this on a steal,” he said.
Jones added that if the contract didn’t give up so much control of the asset, the city would be in a better position to make revenue from the meters today. The company, which operates as Chicago Parking Meters LLC, has financially recouped the $1.2 billion it paid to the city and made millions more off of the deal, which led to increased hourly parking fees soon after its acquisition and has been the subject of a number of lawsuits.
“You could write in your deal [or] contract, ‘you manage this, but we get to say what happens here. We get to say what happens there. We get to maintain public accountability,’ but this bill seems to have been very generous to the private companies, giving them a lot of rights.”
The Reader‘s 2009 investigation showed that Daley and his administration were not transparent about the bidding process and failed to release even basic information about the deal, only giving council members roughly two days to review the agreement before it was brought to a vote.
At the time, the five alders who voted against the deal were Toni Preckwinkle (4th), Leslie Hairston (5th), Billy Ocasio (26th), Scott Waguespack (32nd) and Rey Colon (35th).
Preckwinkle, who has since become Cook County Board president, declined to talk to The TRiiBE on the matter but told the Chicago Defender at the time that she didn’t vote on the deal because they were only given 72 hours to review it: “This is not the first time the city rushed us to vote on a privatization deal. They did the same thing with the Skyway and Midway Airport deals,” she told the Defender.
Waguespack is the only active alderperson today who voted against the deal back then.
“Basically we had two days over the weekend to figure out the deal, and there were two things that kind of threw me off,” Waguespack told The TRiiBE, reflecting on the parking meters. Waguespack said he and his time were already evaluating parking meter rates in his ward and considering raising rates.
“I looked at the finances on it, and it immediately set off like [a] red alert on it. It didn’t seem like it was enough, based on what we thought we could bring in every year,” he said.
The city was bringing in an average revenue between $21 million and $23 million annually through the parking meters, Waguespack said. “We said, look, we could quadruple the rates and get $100 million a year. And nobody wanted to do that,” he explained.
Anthony Beale (9th Ward), a City Council member since 1999, is one of today’s incumbent Black alders who voted in favor of selling off Chicago’s parking meters, alongside Pat Dowell (3rd Ward), Michelle Harris (8th Ward), Walter Burnett (27th Ward) and Mitts. Collectively, they represented majority Black neighborhoods on the South and West Sides.
Dowell declined to speak about the deal. Burnett and Harris have yet to respond to inquiries.
Beale agreed that maintaining the parking meters would have given more money to the city, but blamed the bad economy on why the city had to make the sell. In 2008 the country was undergoing a recession largely due to the housing market.
“The parking meter [deal], we understand [it] was a bad deal. However, if the economy had not taken a turn, then we’d have millions of dollars a year in surplus,” Beale said. “The economy turned at a bad time and the administration used that money to keep from raising taxes off the backs of the people.”
Beale also maintains that the parking meter deal would not fix the “physical problem” of the city government being “bloated,” which he said would need some trimming to gain back funds for the city. Beale was referring to cutting the number of people employed by the city of Chicago.
In the 2025 budget process, Mayor Johnson has been adamant about not cutting city services or laying off city workers such as police officers and firefighters.
Asked why constituents should trust his financial judgment today after he voted for such an economically poor deal in 2008, Beale referred to an unspecified poll that showed that city residents trust their alderman the most “to do right by the city of Chicago.”
Beale said the City Council has learned crucial lessons from the 2008 parking meter deal. That’s the reason, he said, Johnson has received such backlash from the council on matters such as the $300 million proposed property tax hike; the Chicago City Council is becoming more independent from the mayor and learning from past administrations, according to Beale.
Historically, the City Council has voted in alignment with the mayoral administration in office without independently considering its impact, a practice referred to as “rubber stamping.” The council has slowly become more independent, most notably during former Mayor Lori Lightfoot’s term. Black alders such as Beale and Mitts have voted in alignment with mayoral administrations even when such proposals faced community backlash, such as the cop academy in West Garfield Park.
“This is why I’ve been pushing for us to have our own financial analysis department. This is why I keep telling people we need our own legal department. We need to make sure that we have our own lawyers and parliamentarian budget,” Beale said. “We have to rely on the administration, and if the administration is not giving us what we need to make an educated decision, that’s a problem. That’s why we need our own department that we can go to and get the truth.”
Asked if the leasing or selling of public assets to private companies could ever be beneficial to cities or residents, Jones said it may work for smaller cities but not for bigger cities like Chicago.
“Some cities may not have the capacity to manage something and selling it off allows some other entity with enough resources to invest in something, and maybe they do a better job than the city would have done,” Jones said. “I just don’t think that applies in Chicago. I don’t think Chicago is lacking infrastructure or the ability to manage a very valuable public asset.”
Learning from her mistakes of the past, Ald. Mitts said she is looking for more negotiation when it comes to figuring out how to fill the hole in the city’s 2025 budget.
“I mean, a lot of this is negotiable, but we have to be able to sit down and talk about it, and not just decide for the city and then just ram it down as this is what we’re doing,” she said. “No, it has to be collaboration and transparent.”
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