Kelly, it looks like you’re not the only one feeling uncomfortable with the New Yorker cover. Here’s an article discussing the controversy, and here is a link to the New Yorker feature article online, entitled “The Conciliator: Where is Barack Obama Coming From?”
For an idea of some of the possibilities presented of where Obama might be “coming from,” I have pasted the image below. (Are they fist-pumping?) A little further down, I have pasted another image featured by the New Yorker online. Two very different portraits!