What do you want?
The site's aggravating/disappointing history is purely a result of the "too many cooks" problem. The mayor can look out his window and see the site, so naturally he wanted something impressive. Same for the executives of the city's most powerful department store. CTA eyed the property for a rail tunnel. ComEd already had thousands of miles of utility lines snaking under the site. The backers of the theater-district revival saw an opportunity to replace long-destroyed theaters and add to the district's offerings. And I'm just getting started.
Ineptitude on the part of Mills lost them the property and delayed the project's opening until after the bubble had already burst. Consequently, leasing has been sluggish at best, which took down Freed due to no real fault of their own.
The decision to postpone the hotel/residential tower into a second phase was also a poor one, because the financial collapse/credit crunch destroyed any hope of landing financing for the tower phase.
However, now that Block 37 is set in stone (black/white granite, to be specific) I think the opportunities for civic leaders to butt their heads in will go away. A developer needs to be found for the tower, but he doesn't need to worry about the city coming in and dictating any new terms. The foundation's already in the ground, so the footprint and height of the tower are locked in. The only question is the mix of uses, which is largely dependent on what kinds of access are available; a hotel needs some of the base for a lobby, while residential just needs enough for a desk, mailroom, and elevator hall. A blend of the two requires a second elevator core and an even greater chunk of the retail podium for two lobbies.