(native Chicagoan, not living there now)

Selling something with long-term value for a short-term lump sum is the kind of thing a politician would do. He or she isn't going to be around later, so why not get reelected now?

On the other side, Richie Daley didn't have the acumen of David Bowie, who did the same thing:

https://www.investopedia.com/terms/b/bowie-bond.asp

https://www.billboard.com/music/music-news/david-bowies-bowi...!

Just think: who knew that parking meters would continue to throw off money? what happens when self-driving cars are cruising around and no one needs to park anymore?