Talent-wise, he was one of the most devastating fighters that's ever been, especially in his early years. But in a lot of ways, you can't help but feel sorry for him because he never had anyone who really cared for him and would discipline him. Even D'Amato let him get away with a lot because he was going to be one of the great fighters.
For all intents and purposes, he shows the ability to at least want to be good person and lead a healthy life, but he's always been a child and only had his ego fed when it benefited someone else. Tyson always needed a person who legitimately had his best interests as a person in mind, not his money or fame.
I always felt that Tyson should have stayed involved in boxing as a commentator, or in some capacity....because despite his lower 'intelligence', he's always been a good student of the sport, did a lot of studying of classic fighters, and understands the physical sport of it very well. But there's an old saying that you can take the kid out of the street, but not the street out of the kid. It's hard to know what to think of him...sorry for him, ashamed for him, angry at his hedonism, sympathetic, etc. You'd like to think there's some hope for him to find some sort of peace and calmness, but you can't help but suspect it'll all end really badly.