I guess familiarity breeds contempt. And I probably have very different taste in cities than most other fans, I guess, because I rather like St. Louis and I think it's getting better (although slowly). The long-vacant Opera House attached to Scottrade is now open. I discovered the Washington Avenue nightlife area a couple of years ago, and still enjoy the Central West End. Downtown is a lot more lively than it was 3-5 years ago.
Union Station itself can be rather sad sometimes, and the homeless/panhandling problem in the area is more alarming than a lot of other cities. I'm probably immune to that because I've spent so much time in areas with a lot of homeless people, and I don't mind it as much as others might. Since I don't mind those issues so much, I happily overlook those downsides for having other benefits: 1) No competition from other college basketball tournaments. 2) Full staffing by the conference because of headquarters proximity. 3) Most central location for league footprint, despite Wichita being farthest. 4) Local media fully on board 5) Good sized market, very neutral.
The tournament would be completely overshadowed in Chicago. The non-driving transportation is very good (plane, train, etc.), but it's also much more expensive. KC would be a nice option, but you compete with Big 12 and you're reinventing the wheel on implementation and media. There's really no other neutral court option within the league footprint that could pull it off (Des Moines? Quad Cities?), unless you count Intrust as "neutral."
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