In 2008, Chicago’s budget was in a bad place. The city needed money. One way to raise money was to increase property taxes, but what politician wants to do that? So instead, Mayor Richard M. Daley’s administration looked around at the resources the city had, and thought, ‘Any of this worth anything?’ They opted to lease out the city’s metered parking system — to privatize all 36,000 of its parking meters. 

The plan: have private companies bid on operating the meters, modernizing the system, and keeping the profits for a certain number of years. In exchange, they would give Chicago a big lump sum payment. The winning bid was $1.16 billion dollars for a 75-year lease. 

Today’s episode is the story of how that bid got put together, and how it came to be hated. There are kidnapped parking meters, foot chases through City Hall, and trash bags filled with secret documents. 

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This episode was produced by Willa Rubin with help from Luis Gallo and Sam Yellowhorse Kesler. It was edited by Jess Jiang, fact-checked by Vito Emanuel and engineered by Cena Loffredo and Robert Rodriguez. Alex Goldmark is our executive producer.

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