Episode Details

Chicago’s City Council faces a high-stakes showdown over a decades-old parking meter deal, as Stone Peak seeks to buy the rights from Morgan Stanley—but only if the council approves. Mayor Johnson stays neutral, urging direct talks with alderpersons, while some council members delay hearings to scrutinize hundreds of pages of documents, hoping to carve out concessions. Questions swirl about Stone Peak’s ties to an airline linked to ICE transport, prompting calls for deeper investigation. Ald. Bill Conway remains hopeful the matter won’t end up in court, but others are taking their time. A June 25 hearing is now set, with a July vote target—if that stalls, September’s the next chance. This messy saga underscores how hard it is to unwind old contracts when private interests clash with public accountability—and whatever the council decides will shape future deals for years to come.

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