Megan Kelly, not a redhead, is a lawyer. People still refer to her as councelor, barrister, esquire, etc.
If Billy O had been talking to Megan, and had said, "You are a lawyer. You know what I mean." nobody would think anything of it. Even though now she is a top newscastor and TV personality. Would this be disrespect?
Billy O interviews Obama and says, "You're a community organizer. You know what I mean." and Geraldo 'la raza' Rivera's head explodes.
He is angry because Billy O accidentally exposed a fundemental truth, and that is that Obama is wholly unqualified for the position. That is what was made Jerry angry.