[jon1856]

A couple of items here:
1) A commentary by Clarence Page
Obama Cover Has Bite, Benefits

I winced. I'm sure that's what the New Yorker's esteemed editor David Remnick expected me to do when I saw the Barack and Michelle Obama caricature cover that everybody's talking about.

Every so often the quiet little liberal-leaning literary and cultural magazine presents a cover that is intended like a high-class editorial cartoon to startle us. Back in 1993, for example, during a time of high tensions between blacks and Jews, cartoonist Art Spiegelman raised hackles from some and heartfelt praise from others with a cover that depicted a black woman kissing an Orthodox Jewish man.

The controversial Obama cover by artist Barry Blitt is just as startling as that earlier cover, but not nearly as clear in its meaning. If a casual observer didn't know that the New Yorker was a liberal literary and cultural magazine, they might easily believe Blitt's drawing was trying to promote the right-wing smears that it intended to lampoon....
http://www.caglepost.com/column.aspx?c=7058&pg=1

2) How the cartoonist own peers reacted to the cartoon:
http://cagle.com/news/NewYorkerCover/