I'm skeptical of Sailer's authority on the subject; what does Sailer really know about Obama's close friends? Is Sailer a close friend of the President? Moreover, wouldn't all Presidents, regardless of race, naturally accumulate a circle that includes mostly high-class folk? Given his pedigree, Obama's gravitation towards upper-class black people is unremarkable.
That's part of Sailer's point:
Obama’s feelings of class solidarity haven’t been widely discussed, largely because they are rather boring. In a world bedazzled by black entertainers and athletes, and troubled (but intrigued) by black criminals, the black upper class goes almost unnoticed as they engage in respectable rituals such as relaxing at Martha’s Vineyard, where “Skip” Gates has summered for 27 years and the Obamas will be vacationing next month.But Sailer's ignorance of the practical realities of the type of person who usually ascends to the Presidency isn't the biggest problem with his argument. It's that being that type of person doesn't disqualify you from commenting on other types. Just because Obama belongs to the "black overclass" doesn't mean he's unqualified to address race relations and class warfare. Just because you don't have a serious medical issues doesn't mean you can't competently discuss health care reform. It's starkly reminiscent of the Sotomayor attitude; unless you're a certain ethnicity, your aren't as good at reaching judicious decisions.
Sailer has other points in his essay, like the idea that Obama has been "highly prudent" to expose "himself to the disorganized dangers of the Chicago communities he claimed to organize." Sailer implies that Obama is being disingenuous in his attempts to identify with blacks who aren't as well-off as he is.
Here, Sailer again falls short. The President may be a single-minded political operative, but can you really fault him for trying to expand his horizons and integrate into a community with which he had no experience? Perhaps this integration is indicative of a black overclass guilt, but it was just as easily a good-faith effort to try and overcome the natural blinders that were part of his relatively comfortable lifestyle. It may not be the most dedicated display of open-mindedness, but it certainly doesn't mean it's bad.
If Sailer wanted to examine the role of race in the Gates affair, he should've concentrated more on the role race plays in police work and Obama's track record on the rule of law -- not Obama's affiliation with elitist blacks. That should, at least in an ideal world, be nothing more than a footnote in the discussion.