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If you want to know why Daley wins every time no matter what, this explains it better than anything I could ever write:
In the years since then, Chicago has ridden the momentum. It's made big plans, been boosted by big names. Mayor Richard Daley. Oprah Winfrey. Barack Obama.
Now Daley's grip on power is loosened. Oprah is repeatedly rumored to be leaving. President Obama lives somewhere else, and the glow his election brought to Chicago has waned.
(Look to the stars... because they're the only people who can help you. - Maria Bamford)
Maybe - here as in so many other cities - the big plans and the glow masked certain structural defects in the city's financial and political systems that we were able to ignore because of parallel structural defects in the nation's financial and political systems. I'm thinking particularly of the housing bubble that inflated home sales and property taxes and generally served as a national credit card. Things were great and now they're not is a dangerous way of looking at it; you can't separate the two. It's not quite as simple as things aren't great now because they were so great then, but I'd argue that's closer to the truth.
(And maybe, just maybe, Daley's part of the problem.)
Two other more minor infuriations:
1. STOP SWEATING OPRAH. Oprah employs a fair number of people here, and losing the jobs would be unfortunate. An acquaintance works for Harpo, and I'd hate for her to either lose her job or have to move to Los Angeles (unless she wants to move there; it's a nice city), and ditto for the other folks there. But basing the city's mood on the degree of fame of a few of its residents is a fool's errand. I'm much more concerned about, say, ordinances that effect the street-level vibrancy of the local music scene.
Celebrities don't belong to the community; institutions do. If Oprah leaves for LA she'll still be on the glowbox; if the CSO or the Empty Bottle or Taqueria Traspasada #2 disappeared, that would actually make my experience of the city tangibly worse. Famous people are tangentially related to the economic and cultural vibrancy, and by extension the pleasures, of a city - a symptom, not a cause, and a fairly remote one at that.
Actually, if Oprah left, people would stop asking me about Oprah, which would be nice. I did see Steadman once. He's tall!
2. "But through the 1990s, Chicago, by many vital measures, got better. In 1996, on the eve of the Democratic National Convention here, a front-page Wall Street Journal article began, 'This is America's urban paradise. Don't laugh.'"
Fuck back-handed-compliment NYC newspaper trend pieces, which are a dime a dozen and utterly meaningless.