The city might have to hire local TV bankruptcy attorney Peter Francis Geraci if it keeps spending so much on legal fees.
It's not just the $256 million the city paid out in lawsuit settlements and court judgements from 2005 to 2008; it's the $52 million the city spent on private lawyers to pick up the slack, avoid conflicts of interest or do the work apparently too complicated for the lawyers on the city payroll.
City Hall can be a law firm's best friend.
The Reader's Mick Dumke reports that 15 law firms received 80 percent of the city's outside work during the three years ending in 2008.
Most of the names on that list are familiar to political junkies, including the venerable Winston & Strawn, led by former governor Jim Thompson.
By pure coincidence, Thompson's firm donated $94,250 to the mayor, members of the city council, the city clerk and the city treasurer during the time frame Dumke examined.
The city will swear up and down that donations are not linked to contracts, and in some cases that might even be so.
But some firms have a way of putting themselves in the mix. And the city - particularly the police department - has a way of getting itself into legal trouble.
And that's good news for the lawyers. It pays for their cars, their houses, their suits and their fancy lunches.
Except the taxpayers and the victims of the city's wrongdoing.