Sep 28, 2026 · 22 min · 13 segments
A Chicago tech company has raised $85 million in venture capital as it rides the wave of interest in generative…
Jeanne SparrowHost
John PletzGuest
A last-minute political battle is tearing through Chicago City Hall over the proposed $2.53 billion private transfer of the city's infamous parking meter system.
Crane's Justin Lawrence reports, just hours before a scheduled city council vote, opponents managed to delay the decision until September 29th.
Behind the scenes, prominent Loop Capital founder Jim Reynolds joined late-night strategy calls with aldermen, urging them to hold out for bigger financial concessions.
Reynolds, who previously explored buying the meter system himself alongside NBA legend Magic Johnson, advised council members that they still have leverage to squeeze more money out of the buyer, private equity firm Stone Peak Partners.
Under the proposed agreement, Chicago would receive $75 million up front, at least a 2% cut of any future transfers, and a 5% share of the meter system's annual net income.
But dissenters led by Alderman William Hall and Jason Irvin argue the city is settling for the first offer on the table.
They point out that Stone Peak could use interest payments and debt to shrink the city's 5% income slice.
Beyond the financial math, high stakes political rift lines have erupted within the council.
The progressive and Latino caucuses previously stalled negotiations over Stone Peak's ownership of Omni Air, a company linked to federal deportation flights.
Stone Peak announced a deal to sell the airline, satisfying several Latino caucus members.
He argues council members fought hard over deportation flights, but failed to demand that Stone Peak include Black-owned firms in its legal, financial, or lobbying teams for the multi-billion dollar deal.
Meanwhile, supporters of the deal, including Finance Committee Chair Pat Dowell, are dismissing the last-minute push as 11th-hour shenanigans.
They warn that further delays risk landsliding into a lawsuit as the deadline to approve the transfer looms on September 30th.
City Council decides Tuesday whether to lock in the deal or push for one more round of bargaining.
A last-minute political battle is tearing through Chicago City Hall over the proposed $2.53 billion private transfer of the city's infamous parking meter system.
Crane's Justin Lawrence reports, just hours before a scheduled city council vote, opponents managed to delay the decision until September 29th.
Behind the scenes, prominent Loop Capital founder Jim Reynolds joined late-night strategy calls with aldermen, urging them to hold out for bigger financial concessions.
Reynolds, who previously explored buying the meter system himself alongside NBA legend Magic Johnson, advised council members that they still have leverage to squeeze more money out of the buyer, private equity firm Stone Peak Partners.
Under the proposed agreement, Chicago would receive $75 million up front, at least a 2% cut of any future transfers, and a 5% share of the meter system's annual net income.
But dissenters led by Alderman William Hall and Jason Irvin argue the city is settling for the first offer on the table.
They point out that Stone Peak could use interest payments and debt to shrink the city's 5% income slice.
Beyond the financial math, high stakes political rift lines have erupted within the council.
The progressive and Latino caucuses previously stalled negotiations over Stone Peak's ownership of Omni Air, a company linked to federal deportation flights.
Stone Peak announced a deal to sell the airline, satisfying several Latino caucus members.
He argues council members fought hard over deportation flights, but failed to demand that Stone Peak include Black-owned firms in its legal, financial, or lobbying teams for the multi-billion dollar deal.
Meanwhile, supporters of the deal, including Finance Committee Chair Pat Dowell, are dismissing the last-minute push as 11th-hour shenanigans.
They warn that further delays risk landsliding into a lawsuit as the deadline to approve the transfer looms on September 30th.
City Council decides Tuesday whether to lock in the deal or push for one more round of bargaining.
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