IMBY evidently has no clue wtf he's talking about. Chicago doesn't build to compensate for anything. The economy dictates what gets built here, not ego. This isn't Dubai. There are a few buildings here that could easily be supertalls if the developers wanted that. Two Prudential is only 5 ft shy of being a supertall and if the owner/developer cared then all he would have to do is add an extra 5ft on the current spire to make it a supertall.
Anyway, one of the Chicago forumers mentioned about a plan he'd heard or something for the site. He heard it involved another 2000ft tower. I don't know how serious that plan is but I still don't think this is the best site for a 2000 footer.