Daley will have been king of Chicago (with some help and propping from the self-serving Machine of patronage that his father established and perfected he has updated and continued) for 22 years by the time he steps down next year (unless he pulls a Favre. Although he could conceivably pull a Jordan, now that I think about it), but he is leaving the city in economic turmoil that he didn't create, but he did help to exacerbate. Much like his birthday buddy, GWB, Daley didn't make much use of surplus when he had it and squandered billions in bad ideas and in shady deals to politically connected friends. Additionally, of course, there were the scandals that always seemed to escape this Teflon Don: Hired Trucks, Silver Shovel, police misconduct,
and locked-up cronies and associates acting as Fall Guys.
But he did some things right. The tourist areas of Chicago are more tourist (and native) friendly. And, unlike Detroit, moneys have been brought back into the city and the economy is pretty diverse. Of course, that source of revenue is funded most easily by gentrification and cheap TIF handouts - in short, displacing the poor while giving welfare to the rich corporations.
But there's no shortage of good reasons for Daley to quit now. His wife is in poor health. He will have been in office for a longer period than even his father (who, like Harold Washington after him, died in office). The city is losing revenue while costs are raising. And then there's the bondoogles, like the Parking Meter FAIL privatization scheme, which is the one scandal that finally caught up to him in any appreciable (though not legal) manner. So, that's another source of revenue that the city - and whoever leads the city - can not count on to help through the recession.
Whoever occupies the City Hall Royal Throne next has their (thankless) job cut out for them. He or she is going to have to find ways to bring in jobs (which would cure a whole mess of ill, including closing the budget woes and decreasing crime), bring in other sources of revenue, streamline effectiveness and pull out the weeds to loosen the patronage grips of the Machine while tightening the budget. Importantly, the next mayor can do these things while serving the poor and minority populations. It's going to be a tough job.
What we're looking for here would be a Wonk, primarily, but not only. Someone who has proven capabilities and can work with business and community leaders as well as a possibly fractious city council. The new mayor, much like the old, will need to have connections with and wide support from White, Black, and Latino populations and communities (including the diverse White ethnic communities) as well as the diverse social and economic groups.
From what I can see, the list of possible contenders runs from the hopeful but novice Scott Waguespeck (one of the few aldermen to actively object to the recent fiascoes, most notably the Parking Meter privatization. I like him, but it may be too early for him yet. Some more money, name recognition and experience will do him a world of good, though), to the Law & Order types like Sheriff Tom Dart (L&O's like Daley himself don't tend to take care of fundamental problems as much as sweep them under the carpet. Just ask anybody in New York who got 'Guiliani'd'.), to the dynasties like the Jackson family - three of whom are rumored to be thinking about it, to the BIG NAME Rahm Emanuel (a bane to progressives, of course. And a man too much connected to Daley and the hard-line machine to cause any real difference. Except possibly cuss more in front of a mic. Or confront adversaries in the nude) to the already-entrenched Machine Heads like Alderman Burke (no.).
But I think the person who best fits the needs of the city - and, as a bonus, could actually pull off a win - is current City Clerk - and longtime pol - Miguel del Valle. As an extrie bonus, he's actually represented and worked with the poor and Latino populations.