Rival Bidder Reveals Mayor Johnson's Team Secretly Offered $3.3 Billion to Buy Back Chicago's Parking Meters

Chicago alderpersons learned a stunning figure Thursday — not from the mayor, not from his aides, and not from the city's law department, but from one of the private investors now seeking City Council approval to take over the city's parking meter system.

Mayor Brandon Johnson's administration secretly bid approximately $3.3 billion last fall to buy back control of Chicago's privatized parking meters, according to a senior managing director at Stonepeak, the New York-based firm that ultimately won the right to purchase the meter system with a lower bid of about $2.5 billion. The city's offer — roughly $800 million more than Stonepeak's winning bid — was never disclosed to the City Council.

The Moment That Stunned City Hall

The revelation came during a hearing of the City Council's finance committee, when Ald. Matt O'Shea (19th) asked city attorney Jim McDonald how much the Johnson administration had bid to reclaim the meters. McDonald paused, then flatly declined to answer, citing a confidentiality agreement the city had signed.

That's when James Wyper, a Stonepeak senior managing director seated at the front of council chambers, interjected and volunteered the number himself.

"That seems crazy," Wyper said moments after disclosing the $3.3 billion figure.

O'Shea's response drew laughter even from the most skeptical council members: "I'm starting to like Mr. Wyper a whole lot more."

The levity quickly gave way to anger. O'Shea laid out the core concern in sharp terms: "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 added that someone on the fifth floor — where the mayor's office is located — should come down and answer questions. No one from the mayor's office appeared at the hearing.

A Deal Cloaked in Secrecy

The parking meter system has been privately controlled since 2008, when former Mayor Richard M. Daley pushed through a 75-year lease agreement that critics have long called the worst municipal deal in Chicago history. Johnson himself has publicly echoed that sentiment, calling it "the worst municipal deal in the history of municipalities" as recently as last week.

Yet Johnson passed on a chance to undo that deal. His administration quietly entered the bidding process last fall, offered $3.3 billion — and then walked away, determining the cost wasn't worth it. The analysis behind that decision has never been shared with the City Council or the public. The mayor and his aides say they are bound by the confidentiality agreement with Chicago Parking Meters LLC, the entity that currently controls the meters, though they have also refused to let council members or the public see what that agreement actually covers.

The private meter system generated nearly $189 million in revenues last year alone, and the parking spaces themselves are expected to grow in value as the city manages increasingly complex street-use demands in the decades ahead.

Alderpersons Left in the Dark

The secrecy has alarmed a growing number of alderpersons, who say they are now being pressured to vote on a new meter sale — to Stonepeak — without adequate information about the transaction or the process that led to it.

"The fact that all that was going on without us knowing is extremely problematic," said Ald. Andre Vasquez (40th).

The Johnson administration has indicated alderpersons face a deadline next month to act on the proposed Stonepeak deal, though a mayoral spokesperson has since disputed that characterization, saying the administration simply needs to "report out on council's progress" by that date and that alderpersons retain "independent authority" to review the transaction.

What Comes Next

With Stonepeak's proposed takeover of the meter system now before the City Council, alderpersons are demanding far greater transparency before any vote takes place — starting with a full account of what happened during the bidding process and what terms the city negotiated behind closed doors. Thursday's hearing made clear that, at least for now, the Johnson administration has no intention of volunteering those answers on its own.