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Theory #1: Sam Has No Soul
In "The Third Man," Balthazar talked a lot about the value of souls, which may have been a big clue. Perhaps to get out of Hell, Sam had to give away his soul and now he's walking around without a moral compass. This would certainly explain his callousness with women and children. If this is true, Supernatural season 6 may be all about Sam's soul. Maybe the person who has it was whoever Samuel was talking to on the phone about collecting various monsters.