Over at TPM, Jim Sleeper, author of Liberal Racism, has a review of New York Times veteran Gerald Boyd's memoir My Times in Black and White. In it, he makes passing reference to New York liberals being much less able to grapple with the issues his book raised than their counterparts in Chicago. Having lived in both cities, I think I can explain why.
It's a fascinating question that I deal with a bit in my upcoming book. It may not be any more complicated than the fact that people are generally less abrasive and nasty in the Midwest than in the East and if they have a problem with you there's less backstabbing. The politics are still brutal but in a more sporting way. In the book I quote David Wilhelm, Bill Clinton's 1992 campaign manager, who did a stint as head of the DNC: "I'm glad to be back in Chicago where they stab you in the front."
Another big difference is that Upper West Side liberals in N.Y.C. are much more dominant than lakefront liberals in Chicago. The latter had to learn early on to work with "regulars" to get anything done. The culture of dealmaking in the marrow of Chicago politics also helps. Same thing goes with the faculty politics at the University of Chicago. Liberals there had to deal with conservatives. When they did, they found they liked some of them personally and thus were at least a bit less nasty.
As for racial politics, the bigots were so far over the top in Chicago ("Epton. Before It's Too Late" was the slogan of Harold Washington's white opponent) that liberals couldn't obsess over the narcissism of small differences as they did in N.Y.C.