He got out just in time.
At the outset of the recession, the city already was a financial basket case, slipping dramatically further once the Olympics announcement was safely out of the way.
The huge web of legal (and illegal) corruption, including vast inefficiencies of sweetheart deals to politically connected contractors, was difficult enough to maintain during the boom years. It became untenable the moment any economic storm clouds appeared, let alone the "Great Recession."
Over and over again City resources were misappropriated so as to pursue political agendas, such as when top Legal Department personnel and high-priced outside counsel were used to pursue trivial cases against anti-war activists, rather than other cases which might presumably have a greater effect on protecting the taxpayers' bottom line. The Mayor's autocratic style and virtual extinction of any internal opposition meant that small problems festered into big ones because everyone on the inside was afraid to say that the emperor had no clothes -- this was the systemic root of such multimillion dollar boondoggles as the Millennium Park construction fiasco, the Great Loop Flood, the Hired Truck Scandal, etc. Even absent this systemic graft, the structural impediments to reestablishing financial health are enormous, made worse by the state's and county's insolvencies.
Yet perversely, this financial dysfunction was the key to Daley's hold on power. Over and over again, "representatives" (really, business elites) of key constituencies -- gays, Blacks, whites, Latinos, etc. -- were bought off through contracts to private businesses and non-governmental organizations. And thus not only was the fiscal structure perverted, but democracy itself. The illusion of a rainbow supporting the Mayor was regularly trotted out to mask the key class component of Daley's rule, and genuine issues of racism and other forms of oppression trivialized by this fake rainbow of big business supporters.
Your community center might get City funding if you played ball with the Mayor and his pals, but if you were working class and a victim of racist and/or anti-gay police misconduct, at best all you got was the stonewall. What else would you expect from a man who as Cook County States Attorney and later Mayor spent nearly two decades covering for racist torture by former Police Commander Jon Burge and his crew, let alone countless lesser crimes? From education to employment to the environment, those who were connected got the inside track, while the vast majority of Chicagoans were screwed.
Unfortunately the huge obstacles to independent candidacies getting on the ballot -- high signature requirements to get on the ballot, and armies of Democratic Party hack lawyers ready to use the arcane election laws to boot opponents off of the ballot -- ensure that the business elite will choose candidate(s) who have a vested interest in continuing the bullying of his or her predecessor. Real democracy will only come to Chicago when we have a grassroots upsurge, independent of the Democratic and Republican parties, such as we haven't seen in decades.