Jake - Why?
I love the show, but can't figure out why the writers made Jake such a muppet. They go to great lengths to highlight that the role of clerk (Billy) requires the person to be intelligent, manipulative, sensible, conniving, etc. yet viewers are suppose to believe that someone like Jake would fit. Even if he is a junior clerk or intern.
Maybe we're supposed to think Billy took him on as he would never be a real threat, or be able to challenge him in any way. However, I don't see Billy as being that insecure.