I think there's a sort of, you know, very thin way of reading this that says, well, Barack Obama is biracial thus that gives him some understanding of both white America and black America, but that's not really it.
In particular in how [Barack Obama] has directed what you could describe as patronizing remarks to African-American communities.
Humans also tend to find community to be pleasurable, and within the boundaries of community relationships, words - often ironic and self-deprecating - are always spoken that take on other meanings when uttered by others.