I personally don't see TMG as a lost cause. He is at another crossroads in his life, and every time he makes the wrong choice, his options become more limited.
I have worked with murderers, drug dealers, robbers, and all sorts of people that society wrote off at a point. I have seen plenty of them released from prison, only to return to their comfort zones. Most of the guys with the same mindset as TMG have never had a close positive male figure in their lives.
It will be a matter of him finally realizing that his current way of thinking isn't working. Sounds like he may be even considering that he messed up, which IMO is a positive.
Everyone isn't equipped or wired with the stuff it takes to work with these guys. Many of them can't be worked with, and you just protect yourself and family from them. I don't see TMG as that far gone yet... I hope that he finds his way out of the circle that he obviously is in. Life is short, and nothing would be sadder than him wasting what he has been given.
There is life outside of OU. He blew that one, but he still can recover. I blew a few similar opportunities myself, and today I'm doing pretty good for myself/family. Hopefully his mistakes will become stepping stones instead of stumbling blocks. That is how I define my life.....