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When someone says, “Chicago,” a Chicago arises in my mind. But it’s an incomplete Chicago—I can only come up with Michigan Avenue and, off to the south, my boyhood home, as it was in 1970. But even if I were standing at the top of the Willis Tower, looking out over the city, using that as a visual aid as I tried to imagine it, I’d still come up short. Chicago’s too big. Even if I could be granted magical powers and instantaneously grasp Chicago in its entirety (the smell of every gangway, the contents of every box in every attic, the emotional state of every resident), in the very next instant, time moves on, and that Chicago is no more. So, that’s no problem, and it’s even beautiful, but where it gets complicated is in that moment when someone proposes that I judge Chicago, so we can do something about it. When someone asks, “Well, what should we do about Chicago?”—Lord help us. A solution will arise, and it will likely be dunderheaded, because of how pathetically I’ve just underimagined good old Chicago. This is also how we imagine, and then judge, people.
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