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Anyone can sue for any amount of money. That doesn't mean they're going to get it.
A case like the Google guy may be settled out of court and the amount would depend on the extent of his injuries, how it affects his quality of life, how it affects his ability to work, how it affects his spouse (if he has one), etc.
If it goes before a jury, the jury may award "x" amount but it would still have to be approved by a judge. Then, of course, the city would appeal the verdict and the amount would, more than likely, be greatly reduced.
I would think the city would have liability insurance. I can't imagine the city having to pay lawsuits out of a general fund since there are so many of them.
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