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The Tribune asks:
"But Americans also have never sent a Chicagoan to the White House, and one intriguing question posed by his candidacy is whether they are ready to now."
Whether or not Obama's local machine ties should be of concern is a good and interesting question,* but the man who has previously been too black/black-liberation Christian/Muslim/elitist to be president probably does not have to worry whether he's too Chicago, at least in terms of the teeming masses of low-information voters. In fact, I think "too Chicago" might be a step up from all the lunatic things actual voters think that he might be.
*Although I don't see why stories can't just ask "do Obama's machine ties make him an untrustworthy dick? Smart people try to answer this question..." instead of "Will Obama's machine ties make him seem like too much of an untrustworthy dick to the mythical wild average voter? Breaking speculation at 11!" especially when the article goes on to quote nothing but politicians and one historian.