All things being equal, which they’re not, of course, I think Chicago would have probably been a great place for the games. The games would have been extremely compact. At a lot of Olympics, rowing/canoe/kayaking is over an hour away, and often has a separate village. Here they would have been on Lake Michigan, as a centerpiece of the games. They were going to build a jetty for $60 to $80 million to keep the course sheltered. Having it actually work (Lake Michigan gets pretty windy) would have been tough to pull off, but that was the plan. I’m sure having everything centrally located would have helped traffic issues tremendously, although Olympic traffic is never going to be close to good. The subway lines would probably have needed an upgrade (stations near the venues and that sort of thing).
A major advantage, as far as having a quality games, would have been that Daley runs everything. The city council has 48 Democrats and 1 Independent, I think, and every one of them depends on Daley for his seat (if they go against him, he runs someone in the primary against them). An awful lot of votes are unanimous. If he wants something, he gets it, with extremely few exceptions. So he doesn’t have to sell anything politically. So there wouldn’t have been a lot of internal politics.
On the other hand, a consequence of that is that Daley can pretty much set up whatever deals he wants for his friends. The feeling in the city, from pretty much everybody, was that the Olympics would have been a cash cow for Daley’s friends. Some people thought it was worth it, and some people didn’t, but not many people thought there wouldn’t be corruption.
This never felt like a Chicago bid, basically. It felt like a Daley bid. Support was always mixed (although whenever he needed corporate money he got it, because that’s how Chicago works). He was against it before 2005, and then suddenly all for it. I don’t know a lot about the Rio, Madrid, and Tokyo bids, but from here they felt like they had more local fever to them, especially Rio and Madrid. People in Chicago don’t really care how people in Europe and Canada and other places view them. Generally, if the Bears beat the Packers, they’re pretty much happy as far as their self-image goes.
One amusing thing is that Daley has made a career off of backroom deals and saying one thing in public while doing another behind the scenes. Then when he got to the world headquarters of such behavior, he was shocked, simply shocked I tell you, that the vote wasn’t “fair” and based on who had the “best bid,” not that there’s even a good way to objectively identify the best bid.
And the city continually balked at the financial guarantees the IOC wanted. They continually claimed the games would turn a profit, and guarantees were pretty much immaterial, but I am pretty sure that annoyed the IOC, even though they eventually came through with the guarantees, as I understand it.
By the way, permanent facilities are paid for by the LOC, and temporary facilities are paid for by the IOC (including games profits). So the swimming facility is paid for by the LOC, and the media center is paid for by the IOC, and so on, essentially. The stadium for opening and closing ceremonies was supposed to be built in Washington Park. It was going to consist of a field/track, and maybe 10,000 seats, below street level, and then another 70,000 or so seats above street level. After the games the above-street-level part would be removed, and the track/field and the lowest 10,000 seats would remain. That meant that the vast majority of the stadium was temporary, and the city figured the IOC would therefore have to cover it. That’s definitely a Daley-type move. “Hey, we’ll just make almost the whole stadium temporary” and the IOC will have to cover it. Stuff like that may have been minor, but it probably didn’t help. I think there was a lot of tension between “Hey, the IOC wants a legacy” and “No, we won’t have to spend a lot of money building permanent facilities.” It’s pretty much one or the other, and I am pretty sure they were playing it both ways, even on specific venues (I heard rowing was permanent and I heard it wasn’t).
I think inside Chicago it came down to: The Olympics would be neat, but we’re not living and dying over it; it’s definitely going to be corrupt and we’re going to get promised a lot of permanent stuff that’s not going to happen; we’re going to end up paying taxes to cover a lot of it.
For the IOC it possibly came down to: The Olympics in Rio would be awesome; Rio is dying to have it; the USOC is a pain in the ass; we know corruption when we see it, and if Utah had ethical problems (in the bidding process), Chicago is going to be off the charts (after the bid is awarded).