Interesting to say the least. 

It is quotes like the following that has people shaking their head about West:

“I think my dear brother Barack Obama has a certain fear of free black men,” West says. “It’s understandable. As a young brother who grows up in a white context, brilliant African father, he’s always had to fear being a white man with black skin. All he has known culturally is white. He is just as human as I am, but that is his cultural formation. When he meets an independent black brother, it is frightening. And that’s true for a white brother. When you get a white brother who meets a free, independent black man, they got to be mature to really embrace fully what the brother is saying to them. It’s a tension, given the history. It can be overcome. Obama, coming out of Kansas influence, white, loving grandparents, coming out of Hawaii and Indonesia, when he meets these independent black folk who have a history of slavery, Jim Crow, Jane Crow and so on, he is very apprehensive. He has a certain rootlessness, a deracination. It is understandable."

This goes back to the issue that popped up during the campaign: is he black enough? It seems to me that West is engaging in the continuation of the simplification of race, identity, and race relations.  Either Obama roots himself within white culture or in black culture.  There is no other alternative.  To do neither leads to rootlessness, and this leads to a certain fear of free black men, with their "history of slavery, Jim Crow, Jane Crow and so on..."

In dealing with the entire spectrum of socio-economic issues that are facing this country, it becomes necessary at times to make broad generalizations about groups of people.  To get into all of the subtle nuances would take forever, and the point needing to be made lost.  But again it seems to me that West has embraced the simplifications so that Obama has experienced "deracination" because he does identify himself racially in a way West thinks he should given the few options available to Obama.

I think Adam Serwer said it well:

Obama's struggle to find peace with himself is essentially the opposite of "deracination," a term that takes on all the force of an epithet here. Obama is lambasted as a Kenyan anti-colonialist by the likes of Newt Gingrich, and as a wide-eyed surrogate of "upper middle class white and Jewish men" by the likes of West. To have one group of morons question your citizenship while others question your blackness. To have one's very being interrogated by those who, because of their own pathologies, see your difference as a kind of terrible mistake, an anomaly to be soothed with toxic balm of archaic social binaries, this is what it means to be black, and also a mutt.

West undermines his credibility by ranting spitefully about all the ways in which Obama has personally snubbed him. Kinda pathetic. It's too bad because he could have just gone with the policy complaints.