What I don't get is that in the beginning of season six we see Tony barely survive a gun shot wound in the stomach after being in a coma only to be killed at the end.
He was basically given a second chance, by surviving nearly the impossible, basically given a second chance to reform, change, etc. But he didn't, and in doing so, pissed away his second chance/redemption and sealed his fate.
That's interesting. I never thought that's his second chance. He blew it away. I think you are absolutely correct. He should've retired. (P.s. how is the past form of should? I think I didn't write it down correct?)
