Over the weekend I came across this man on Youtube pretending to be a ghetto art critic and connoisseur. It turns out hes actually a painter named Jayson Musson who invented this character called Hennesy Youngman. That in itself is a caricature but Musson's paintings have a lot of text and political personalities within them.
HENNESSY YOUNGMAN Link to his Youtube Videos
So this image clearly is about the Twin Towers but I'm thinking the artist was trying to imagine if had happened ten years later. Barack Obama has become a superhero figure saving the World Trade Center from the terrorist attacks. The speech: "Not on my watch!" refering to his term as his watch over the country, like a superhero protects his city Obama protects America. The caricature of Obama isnt an exact look alike but more of a representation, without the speech bubble it would be hard to tell who it was. Comparativley Obama is far too small and the airplane is too large where the buildings look small but I could say they were in the distance.
This image is in a series of Obama saving the world through time, making our president to be a great leader by taking care of the whole worlds problems but I cant tell if the artist is being serious or sarcastic.