For me, the litmus test for Daley is this:
When the Elder Daley wanted to create a new University for the city of Chicago, he looked over a bunch of sites near the loop. Of all the sites, only one area was considered safe enough to go into at night: Greektown, a strong base of Daley support. Daley said “To hell with them” and built the university over much of Greektown.
The only way he left office was in a casket.
As for the younger Daley, he waned to build a new airport in Chicago. When he looked over the area, he realized it would be built over the largest white area in South Chicago. Too chickenshit to do anything down there, he turned around and started blocking the Peotone proposal.
Thing is, had he gone ahead with the building of the Hegewisch airport, we might be getting a workable schedule for the rebuilding of the O’Hare Airport. That southern airport would make for a much more airplane-friendly Midway (ever seen how tightly things are packed there? They have to use engines in overdrive to stop the planes), and could even work overtime as O’Hare was rebuilt into a modern airport.
But…instead we got him trying to block Peotone while rebuilding O’Hare in his image.
In the end, Mr. Daley will be remembered well (as people will have to, as they’ve kept him in office too long to think objectively about him) but don’t be surprised is he misses the “Best of Chicago” list by a wide margin. He’s a good administrator, but when things NEED to be done he’s not the person to do them.