I think Brady means Sam's life is hell because of the way he has unknowingly been living his 'destiny' and all the awful stuff he has gone through.
I'm surprised you didn't remark on Dean's reaction when Sam went to kill Brady.
I read the look on Dean's face as though he didn't want Sam to do it but that he knew Sam HAD to. Almost like when Sam had to shoot Madison, and Dean would rather have done it to spare Sam the pain.
Difference being, by this point in the show Dean knows he can't spare Sam the pain and lets Sam have his vengeance, even though he wishes his little brother hadn't gotten hard enough to want to do it himself.
Am I making any sense?
It's a look that says Dean didn't like it, but not in a disapproving way but in a sad way.
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I'm surprised you didn't remark on Dean's reaction when Sam went to kill Brady.
I read the look on Dean's face as though he didn't want Sam to do it but that he knew Sam HAD to. Almost like when Sam had to shoot Madison, and Dean would rather have done it to spare Sam the pain.
Difference being, by this point in the show Dean knows he can't spare Sam the pain and lets Sam have his vengeance, even though he wishes his little brother hadn't gotten hard enough to want to do it himself.
Am I making any sense?
It's a look that says Dean didn't like it, but not in a disapproving way but in a sad way.