[defrost]

I'm outside the US.

Typically I'd think of a city having a contract with a service company for them to manage and service a city's parking meters for a cut of the revenue, "the city in control of its subcontractors".

This reads very much as the City of Chicago tightly subcontracted to maintain the 72 year revenue stream of Chicago Parking Meters LLC, "the tail wagging the dog".

[knubie]

As per the article Chicago needed cash, and quickly, to fill a budget shortfall, so they sold a lease up front to fill the hole.

[defrost]

As per the implication in the article, the former Mayor and close circle pushed an asymmetric "cash now, big trouble later" deal through in exchange for (implied) kickbacks and as a result of leaving office with zero chance of having to deal with the consequences.

There's much to be said for tying some form of liability to office holders who make a deal.

[xeromal]

Sounds very much like that story of Jacob and Esau where Esau sold his birthright for a bowl of soup.