We tend to see the tragedy of What Is And What Should Never Be as Dean and Sam not being close in that dream world as they are in their reality, but what gets me is the reason for that. Dean’s wish was that his mother never died, and in that world — the world that was created in his own head — she raised a family, John was a regular dad who played in a baseball league, and Sam got to go to Stanford and get engaged to Jess. But Dean was still a drunk who lied and stole even from his own family. He was a disappointment to his mother and estranged from his brother. He couldn’t even image himself with Cassie or Lisa. He had to make up a girlfriend from a beer ad. So, the real tragedy of What Is And What Should Never Be is that Dean thinks so little of himself that he couldn’t image himself as a better person. He thinks that his dishonesty, drinking, and stealing are inherent and not a result of the way he was raised and the life he’s lead. 

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    OOOOOUUUCCCHH
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    John was aware that leaving Dean in a reform home might be viewed negatively by others, by Sam at least, and that Sam...
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    This. My feelings for this episode, summed up way better than I could.
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