This may sound odd, but I think I'll always remember Henry as a guy who seems to be very sensitive about things. After reading some of his interviews, he strikes me as someone who is very insecure. One that stuck out was when he kept repeating the fact that he didn't want people to think that he was big and dumb. He said something to the effect he should have been a lawyer so people knew that he was smart. He was being totally serious. I might not be doing it justice, but it came across in the interview as some really insecure, whining, shit. Another thing that I always remember him for was getting to be the ECW champion because he implied that he would file discrimination charges against the WWE for the Michael Hayes incident that led to Hayes being moved to a lower position. I understand that something like that could be taken as very serious, but my opinion changed once Booker T spoke out about it. Booker wasn't with the WWE at the time and said that Henry blew it way out of proportion, and that Hayes wasn't a racist at all. Along with all that, Henry has made a lot of comments about getting mad when people "start joking with me because they think I'm some jolly fat man". At the end of the day I think Henry hates the fact that he has to play the "jolly fat man" on TV because he totally failed at being a monster heel.
As far as in ring work goes, he was pretty damn bad. However, I thought his sexual chocolate gimmick in the 90's was pretty funny at times. He is a guy who was brought in after being an Olympic power lifter and signed a 10 year, million dollar a year contract. For that kind of money, he was a total failure.
He had the size, strength, and look at be a force in the WWE, and it never really happened. In all honesty, I don't think anyone will notice when he retires.