This is truly U N B E L I E V E A B L E in case you're interested in watching this.
Similar to Edmonton's current budget deficit, Chicago was facing a $150m deficit in 2008.
So the city, with the overwhelming support of council, decided to sell the rights to their 36,000 metered parking spaces to the bank Morgan Stanley for 75 years for $1.16 billion. Chicago would then not have a deficit and could invest the money for future infrastructure projects.
Parking rates at the time were 25 to 50 cents per hour. Morgan Stanley quickly quadrupled the rates and few years later Chicago had the most expensive parking rates in the country.
On top of it, if city construction was going on or a parade where some of those parking spots could not be used, the city had to pay Morgan Stanley for lost revenue. Also people who had disabled placards and didn't have to pay - well the city had to also make up that lost revenue to the tune of 10s of millions of dollars. And even during the pandemic during open streets, and increasing space for outdoor dining, the city had to reimburse the bank. As it turned out, Morgan Stanley has recouped their $1.16B plus made an extra $500 million with 60 years to go in the contract.
There is more incredibly idiotic parts of the deal outlined in the video. Oh, and Chicago spent all the money it made in the deal in 2 years an will have to continue to pay the bank for any lost parking revenue due to the above mentioned reasons.