Not going into a long discussion but Daley really ruined the finance of the City of Chicago. Case in point: the infamous parking deal.
https://www.bettergov.org/news/chicagos-parking-meter-deal-a-lesson-in-worst-practices
From Wikipedia:
Daley received criticism when family, personal friends, and political allies disproportionately benefited from city contracting. He took office in a city with regular annual budget surpluses and left the city with massive structural deficits. His budgets ran up the largest deficits in Chicago history. A national leader in privatization, he temporarily reduced budgetary shortfalls by leasing and selling public assets to private corporations, but this practice removed future sources of revenue, contributing to the city’s near insolvency at the end of his tenure.