Chicago has done some crazy things. Such as, they borrowed against anticipated parking meter revenues for the next 75 years. They got about $1 billion, as I recall, from that deal.
But that money was all gone within a year.
Chicago cannot blame their problems on Republicans. Democrats have run Chicago for generations, so if Rahm Emmanuel tries to make some political statement, he can’t realistically do so.
I think they have considered some things, such as professional services tax, which would be a tax on your CPA or law firms business. But that probably can’t raise enough revenue to balance their budget.
Tobacco Settlement Disease. It ain’t just Chicago.