Interesting. Let me offer my two cents.
First form the New Yorker's editor:
http://www.huffingtonpost.com/2008/07/13/david-remnick-on-emnew-yo_n_112456.html
"This cover has quickly become very controversial. The Obama campaign
has called it "tasteless and offensive." Why did you run it?
Obviously I wouldn't have run a cover just to get attention — I ran
the cover because I thought it had something to say. What I think it
does is hold up a mirror to the prejudice and dark imaginings about
Barack Obama's — both Obamas' — past, and their politics. I can't
speak for anyone else's interpretations, all I can say is that it
combines a number of images that have been propagated, not by everyone
on the right but by some, about Obama's supposed "lack of patriotism"
or his being "soft on terrorism" or the idiotic notion that somehow
Michelle Obama is the second coming of the Weathermen or most violent
Black Panthers. That somehow all this is going to come to the Oval
Office.