Ultimately, I still believe that we'll never know exactly what happened but here's what I've gathered after having conversations with members of No Games Chicago. In essence, one of the reasons that Chicago lost was that Daley's machine politics didn't transfer over to the IOC all that well. For instance, Daley said several untruths and many of these untruths were eventually discovered by the IOC. So, by the end, his credibility was weakened. Daley claimed that Chicago has a solid infrastructure. In fact, if Chicago were to host the games the city would need to totally transform its train system and highway system. He claimed that all the Olympics sites would be compacted next to each other. In fact, the equestrian would be held in Wisconsin. His biggest whopper was that there really isn't much corruption in the city of Chicago. He claimed the corruption really occurred in the Governor's office (Blagojevich) and with his ouster, most of the corruption was rooted out. As the truth was brought to light, Daley's credibility was weakened.
Second, No Games Chicago was the only group of its kind until the end. There was no equivalent in Madrid, Rio, and Tokyo only formed one such group at the end. In fact, in June, No Games Chicago went to Switzerland to lobby the IOC not to bring the games to Chicago, and the IOC said they'd never remembered a group like their's that locally was lobbying not to have their city get the games. No Games Chicago was interviewed by several Tokyo media in June and the media showed them video of similar demonstrations by Tokyo residents against the bid coming there. Yet, there was no organized group against the bid. So, in October, No Games Chicago had their equivalent in Tokyo. Is it merely a coincidence that those two cities were the first two knocked out? Also, support for the games fell in Chicago below 50% (and I believe in Tokyo) and that's always a magic number with the IOC. Once that happened, the bid was doomed.
President Obama also didn't help the bid any. He got criticism for going at all. As such, he shortened the trip tremendously. He and his entourage arrived at about 9 AM local time. That was two private planes (including Air Force One) and a charter plane. The logistics of that visit called for major roads and highways to be blocked off. Well, at 9 AM, that means a lot of residents of Copenhagen had difficulty getting to work. Furthermore, the President spent less than half a day in Copenhagen. The other leaders, from Brazil, Spain and Japan, spent a couple days in Copenhagen. Like anyone else, the IOC likes to be schmoozed. So, this clearly put Chicago at a disadvantage. Whereas the other world leaders spent days fraternizing with the IOC and locals, Obama was in and out before anyone could see him.
The bid in Madrid appears to have been doomed from the beginning. With Barcelona getting the games in 1992, it doesn't appear as though the IOC ever had any intention of giving them Spain the games again so soon. Their bid was thus propped up by Juan Antonio Samaranch. He's the former head of the IOC that was now leading the Madrid bid. In fact, about half the IOC members were put there by Samaranch. He pleaded personally with them to give Madrid the bid. They nearly got it even though it doesn't appear as though it had anything positive to offer besides him.
That leaves Rio. Rio, it appears, got it because it had the most reasons to get it and the least negative reasons to get it. First, it would be the first South American city to host the games. That's no small factor. Second, there was no visible opposition like in Chicago and Tokyo. Third, the President of Brazil promised to put the full weight of the country behind the bid. It won't merely be Rio funding the games but the country of Brazil. In the U.S., our federal government is barred from doing the same thing. With the full backing of the national government, the city appearing united in favor of the bid, and the opportunity to give the bid to a South American city, Rio got the bid.
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