These are two sketches from a New Yorker job that didn't work out. The story was about Obama in Chicago and it didn't boil down to a single image too easily. So they went with a photograph, and who can blame them?
The first one is just Obama bestriding the city like a colossus, pretty standard stuff.
But the second one, if it'd worked, would've been more interesting. It's supposed to be the big Picasso in the middle of Dailey Plaza transformed into an Obama caricature. It needs more work, but it's an idea.
Update: this would've run in the same issue as Barry Blitt's instantly-infamous Obama cover. I think mine might have looked a little puny in comparison.