“Makes me wonder how much of Sam wanting to leave was him perceiving that Dean wanted him to stay? Just to “not do what you tell me to do”. Because once Dean tells him it’s okay with him if he goes after a different life, he comes back.”
Interesting observation, JBB. How much of Sam’s behavior was just defiance for the sake of defiance? I remember in “In My Time of Dying” right before John is going to die, Sam starts picking a fight. John refuses to take the bait and says something like “Half the time when we’re fighting, I don’t even know what we’re fighting about — we’re just butting heads…”. Your observation makes me wonder if some of Sam’s hostility toward John wasn’t necessarily about not wanting to follow orders, but may have been partly about just wanting to feel like he was making his own choices, so he intentionally wanted to go the “other” way from what was being asked of him.
Another side note, there have been a few times when Sam used Dean’s fear of abandonment against him, to try to get Dean to comply with something Sam wanted him to do. I wonder if this was one of them.