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Chicago has a habit of not even negotiating good terms, while turning over public infrastructure to private enterprise in 99 year leases. A short term cash fix comes at the expense of bleeding citizens for the next 5 generations or so. The Skyway. The parking garages. The parking meters.

Traffic law enforcement going to faulty and corrupt traffic camera companies, based/excused upon arguments that are suspect at best. E.g. red light cameras, particularly but not only with the yellow cycles reduce to or below the legal minimum time apparently solely to increase the number of infractions, leading to increased occurrences of accidents and particularly of more dangerous accidents.

And that's not even getting into the decades of "The Machine" that politicized and monetized anything with a pocket to shake a nickle out of.

Chicago has upsides. Per my first line (in my other comment here, I guess), some even find the politics to be so: As long as you enjoy it as a contact sport.




ironically, the current mayor got a big commission check from the banks for facilitating some of those bad deals.




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