West's whole schtick on Obama feels like it's been an extended riff of the Jesse Jackson "cut his nuts off" comment, a member of the old guard feeling that Obama hasn't paid his dues and isn't really authentic.
As a honkey I generally avoid commenting on internal conflicts in other communities, but West really seemed to cross the line in how personal he got, and most of his political analysis seemed directly lifted from a #slatepitch about how Obama could've gotten a British style National Health System if only he really tried.
Honestly I don't think West and Jackson were on the same side of that disconnect. West was an early Obama supporter, an intellectual, and a far leftist. I don't think of him as a member of the "black establishment" that Sharpton, Jackson, and other civil rights relics have been a part of over the decades. You can see why Obama appealed to leftists and intellectuals - he's basically from that world. In fact he has more connection to it than the Civil Rights era. When Obama first ran for office in Illinois he was attacked for being a black elitist who didn't understand actual black people; Bobby Rush beat him in an election by making those arguments.
Basically Jackson is from that Bobby Rush cloth IMO, whereas West isn't. I think West is just a delusional leftist who is mad Obama didn't invite him to the White House enough. West isn't nearly as respected as he once was as an intellectual, and part of it has to do with him basically becoming a shitty pundit prone to hyperbole and ugly racial comments about Obama's family.