I have this theory that while growing up Sam was always a little too close to Dean and then the first time he got drunk he came back to the motel room and kissed Dean but got pushed away and told that it was wrong. So to try to get away from his feeling and the pain he felt every time he looked at his brother he went to Stanford and found Jess. She was the first person he could connect with in the same way he had with Dean.
Leo: Listen up. Our ground game isn’t working; we’re gonna put the ball in the air. If we’re gonna walk into walls, I want us running into them full-speed.
Josh: What are you saying?
Leo: Well, you can start by telling the Hill the President’s named his nominees to the FEC. And we’re gonna lose some of these battles. And we might even lose the White House. But we’re not going to be threatened by issues: we’re going to put ‘em front and center. We’re gonna raise the level of public debate in this country, and let that be our legacy. That sound alright to you Josh?
Josh: I serve at the pleasure of the President of the United States.
CJ: I serve at the pleasure of the President.
Sam: I serve at the pleasure of President Bartlet.
Toby: I serve at the pleasure of the President.