Maybe I'm speaking as a person too young to know Flair's legacy, but here it is...
Flair has NEVER been good to me.
I remember when I first started watching WCW, I happened to discover it one night flipping through channels. I was a WWF fan in '91, and only knew about WCW a little after '93 began. WCW was like the WWF without the gimmicks. It had real wrestlers and guys who seemed normal guys compared to The Undertaker and Doink. I started liking Sting, the true hero/draw for WCW, Vader, one of the best big man heels I've seen, and some of the mid-carders. Then, when Hogan was signed, I started seeing Ric Flair, this cocky, blonde playboy who was supposed to be the champion and better than everyone. His match against Sting where he won the WCW Title, I literally wondered how Flair could have won without cheating. Then it became a trend.
As I watched The Four Horsemen, it became apparent that Flair could not win without help. Every match, every situation, Anderson helped him, Pillman helped him, Benoit, McMichael, Woman, Jimmy Hart, no matter who or what, Flair ALWAYS needed cheating to win. He never faced jobbers, and needed shortcut after shortcut to win. Brass knuckles, chairs, handcuffs, bribes for heel turns, suitcases...I started wondering just why was he so great.
I know the heel philosophy was to cheat to win, but I also know that even the suckiest of heels needs to beat somebody on their own. The greatest heels not only could cheat to win, but you have to think that they have some shot on their own of winning. Edge is portrayed as a cowardly heel, running away and using shortcuts to win, but he also had the ability to hit the spear for a quick win, or get a roll-up sneakily for the pin. Maybe it's not a dominant win but at least he won without help. When Flair was a face, he almost never won a match. And his time in the WWE, even when he's a face, he's still "the dirtest player in the game" and needs shortcuts to win.
Why am I saying all of this? Because I'm asking why does he deserve another title reign? Besides being CEO of the WWE, HHH's "manager" and the veteran looking for one last hurrah, how can we even say he can do it again? He hasn't had a decent match in years. All he does is chop and go "woo" the whole time, maybe hit a shin breaker and eventually try to apply the Figure Four and strut around. He doesn't even try to wrestle anymore. Flair should be someone else's manager right now, whether it be face or heel, because his time is done. If he wants to quit, let him. I don't know what kind of program they see him in or what they offered him, but I hope it's not at the behest of younger guys ready for the spotlight.