I’m not completely sure what to make of this new ad from the McCain campaign linking Obama to Chicago machine politics. On the one hand, it does not go too overly racial in the imagery. Of the four people whom the ad links to Obama, only one, Emil Jones, is black (though the problem with Obama's link to Jones is never made clear).
Although Obama was a community organizer from the South Side and represented the area as a state senator, his responsibilities were in state-level government, not city-level: He was not on the City Council or the mayor of Chicago. It's not that he didn't know or interact with members of Chicago's machine; of course he did, because politicians from different levels of government know one another and have to work on projects together. My point is that he was not a city official, so tying him to the city's urban machine strikes me as a stretch. Like the ribald mockery of his "community organizer" background, it also smacks of subtly trying to "urbanize" Obama.
Is that racist? I don't know. Lots of Americans are wary of the cities and city life, even when those cities are run by and largely populated with white urbanites. And maybe I'm just reflexively suspicious. But it does seem like the McCain people want to find ways to blacken or at least, uh, "urbanize" Obama whenever possible.