That's really, really lazy logic you're (not) trying to compute. If the send-your-enemies-glitter guy wasn't in it for the money, why'd he sell his site for money?
Also Chicago sold the rights in a fire sale due to some combination of budget shortfall, corruption, and incompetence. After the fact, independent appraisers found the contract should have been worth more than $2B, but was sold for just over $1B.
Google 'chicago parking meter privatization' for more info (some of it likely to be biased).