Chicago officials pick apart parking meter deal, buyer’s ICE deportation ties

Council is required to vote to approve the sale because the parking infrastructure will revert back to city ownership in 2083, 75 years after former Mayor Richard M. Daley sold it for $1.15 billion to assist the cash-strapped city in 2008.

Wyper provided most information that council said was kept from it by the mayor’s office and city’s legal department.

Opponents to the deal, and of Mayor Brandon Johnson, gained new insight into the mayor’s own bid for the meters when Wyper told them he believed the offer to be roughly $3.3 billion, multiple times more than the city sold them for in 2008 – and well above the firm’s current agreed price.

Johnson didn’t notify the council before submitting the city’s bid, and earlier this year announced his office had dropped the exploration of a buyback, citing the long-term loss to the city.

Jim McDonald, a city attorney, wouldn’t confirm details of the city’s bid.

“The city executed a confidentiality letter agreement last year,” McDonald said before Wyper said it had been waived. 

“There's ambiguity in the clarifications that [Chicago Parking Meters] provided as to whether or not that fully provides us the ability to talk to the city council about the documents you're referring to,” McDonald said.

Some aldermen expressed concern over the terms because the council didn’t get a chance to renegotiate some previous terms, such as the city being required to pay any time parking is out of commission, such as construction.

Wyper told members of the council that the firm will be committed to communication with city officials if the sale goes through.

“That channel has not existed historically and does not exist today. It is crazy that time and again the city has not availed itself of the myriad existing abilities to avoid true-up payments. If you want a holiday, you add a couple – a few more parking meters somewhere that doesn't have a huge impact to your district,” Wyper said.

The taxpayer cost of true-up payments between 2009-2024 was $161 million, according to a report by the council’s Office of Financial Analysis.

Wyper also answered for companies Stonepeak has shares in or ownership of, including Seapeak, which transports Russian oil, and Omni Air, which has contracts with the Department of Homeland Security for charter deportation flights.

Alderman Jessie Fuentes referred to reports of increasingly poor conditions for detainees after the firm took over ownership in 2025, sparking a back and forth with Wyper.

“Last fall, you had a flight to the continent of Asia and individuals were shackled for up to 82 hours,” Fuentes said. “Are you aware of that?”

Wyper said he was not aware of any wrongdoing within the company, though he expressed concern for the actions of ICE under the current administration, calling them "abhorrent."

“We have discovered no evidence of wrongdoing or treatment outside the guidelines, which certainly does not include that sort of thing,” Wyper said. “There are Department of Homeland Security officers and employees on our planes, we fly them.”

The deadline for approval of the deal has been extended multiple times without notice to the council, but is now July 24.

If the council decides not to approve the deal, ownership will not change hands and Stonepeak will seek reimbursement for legal fees, per city statute.