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CHICAGO — Alderpeople learned Thursday that Mayor Brandon Johnson’s administration secretly offered about $3.3 billion last fall to reclaim control of the city’s parking meters — a whopping $800 million more than the next-highest bidder.
But the City Council members didn’t get those key details from the mayor, his aides or any other city officials.
Instead, one of the investors set to buy the rights to the meters blurted out those figures after a city lawyer refused.
During a hearing of the council’s finance committee, Ald. Matt O’Shea (19th) asked the city attorney, Jim McDonald, how much the Johnson administration bid to buy back city control of the meter system.
McDonald paused a moment and then said flatly that the bid information was subject to a confidentiality agreement the city had signed. So he wouldn’t answer.
That’s when James Wyper jumped in and said he would.
Wyper was sitting at a table at the front of council chambers next to the committee chair, Ald. Pat Dowell (3rd). He was ready to speak on behalf of Stonepeak, the New York-based firm where he’s a senior managing director, about its impending purchase of the meter rights. He was so ready to speak that he repeatedly interjected, offering to share what city officials wouldn’t.
“Well, I’m starting to like Mr. Wyper a whole lot more,” O’Shea said.
That got even the most skeptical alderpeople laughing.
Wyper said he understood the city’s bid was about $3.3 billion.
“That seems crazy,” Wyper said a few minutes later.
Wyper and his colleagues said Stonepeak bid about $2.5 billion — which proved to be the winner after the city walked away. Stonepeak is now seeking City Council approval for its proposed takeover of the meter system. And the mayor is trying to avoid talking about it.
RELATED: Why Is Mayor Johnson Keeping Secrets About The Parking Meter Deal?
City officials have previously said the city’s bid was about $3 billion, but refused to offer specifics or share their calculations for arriving at that figure. The $800 million difference with Stonepeak’s bid left alderpeople asking more questions. Some railed against the mayor and the city’s law department for failing to disclose the information sooner.
“So the mayor put a bid in six months ago, $3.3 billion, for parking meters that we don’t have the money for, didn’t disclose that to anybody in the City Council, and then agreed to a non-disclosure agreement, did not have to talk about said agreements, and now is unwilling to share all this information,” O’Shea said. “I’m guessing someone on the fifth floor is listening right now, and I think we need to get someone down here to answer some of these questions.”
The mayor’s office is on the fifth floor. But no one from the office walked down to council chambers on the second floor to appear at the hearing.
In a statement afterward, a spokesperson for the mayor said when Johnson decided to drop the city’s bid in January, he highlighted the high cost of regaining control of the meters. Throughout its bid, the city complied with terms set by Morgan Stanley, the investment bank that holds the meter concession now, the spokesperson said.
“The bid process was conducted as a closed process. The City had no control over the structure of the bid process or its terms,” the statement said. Once the city ended its bid, “it publicly disclosed to the City Council that it had participated in the bidding process.”
The saga of Chicago’s parking meter deal has been unfolding for nearly two decades. In 2008, former Mayor Richard M. Daley agreed to lease the city’s 36,000 meters for 75 years to Chicago Parking Meters LLC, an entity led by Morgan Stanley. The city received about $1.2 billion up front, while CPM got to keep the money fed into the meters.
By the end of last year, the company reported about $2.2 billion in total revenues.
But Morgan Stanley and its partners decided to sell the meter concession, and with the help of consultants and outside lawyers, the Johnson administration worked on its bid behind closed doors for months last year. During that process, the city signed a confidentiality agreement barring them from sharing details of the bid, city officials have said.
The mayor and his team have cited that agreement while refusing to disclose what led them to walk away from the meter buyback.
Stonepeak then became the highest bidder. Along with its partners, the firm reached an agreement to buy out Chicago Parking Meters. Under terms of the 2008 contract, the City Council has to approve the sale.
That’s what prompted the finance committee meeting Thursday.
In response to questions from alderpeople, leaders of Stonepeak and CPM said they too were frustrated with Johnson’s team for keeping information from the City Council. They all disputed the mayor’s claim that the confidentiality agreement still keeps him from talking.
When McDonald said the agreement remains in effect until August 2027, Wyper piped up again.
“That confidentiality agreement has been waived for some period of time,” he said, later adding it was lifted on June 12.
McDonald disagreed, arguing the city might need additional documentation. “There is ambiguity in the clarifications CPM sent — ”
“We can sign it literally right now,” Wyper said.
Wyper’s colleague Rob Kupchak told the committee that during meetings in March, Johnson aides instructed them not to share information with alderpeople. “We were told that they wanted to control the narrative of the deal to City Council.”
Throughout the hearing, Stonepeak also faced tough questions, including a number focused on Omni Air International, a contractor for the Department of Homeland Security that has provided flights for dozens of deportations since Stonepeak acquired it in 2025.
Wyper said Stonepeak is trying to sell the company and expressed sympathy for immigrants, noting he has a family member with ties to Latin America.
“I think you should be using this opportunity to shout as loud as you can about the behaviors of DHS,” Wyper said.
“Again, I appreciate the bleeding heart right now,” said Ald. Andre Vasquez (40th). But “y’all weren’t doing that when you decided to buy it. So I don’t need it here.”
As planned, the finance committee did not vote on Stonepeak’s proposed purchase of the meter rights. CPM and Stonepeak leaders said they’ve given the full council a July 24 deadline to hold a vote.
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Twitter @mickeyd1971 More by Mick Dumke
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