7. Ric Flair
Speaking of retirees and retirement matches at a Wrestlemania, I bring you Ric Flair. No stranger to both astronomical highs and oceanic lows in this business, Flair just cant stop, can he? Ric is the rare wrestler who has won and lost almost everything there is during his career. Big matches, titles, his job, money, (unfortunately so) friends and family. For a business he gave so much to, Im not sure what his return really looks like. (I may examine that further sometime down the road.) The fact of the matter is Flair is one of the most brilliant workers in the ring and out but couldnt stop being The Man outside of the ring. There are stories of his spending sprees all over the internet told from friends, family, fans, co-workers that show just how much of The Nature Boy is naturally Ric. Therein lies the conundrum. If I said Ric Flair is owed and owes a lot of money, what would you say? If you already know, probably that it has been known for years, no big deal. He was one of the biggest names of his heyday and his Woos still fill arenas to this day. Before a show, while wrestlers do Knife-Edge Chops, when he appears. If he is broke (probably many times over) he needs to appear on TV, doesnt he? Not necessarily. Yes, he could make the occasional appearance like backstage employees like Ron Simmons, Dusty Rhodes and even his righthand (Horse)man, Arn Anderson. But for the most part Flair can just get a position where he speaks directly to the talent about having a presence in front of WWE cameras. He can help add things to a current guys repertoire to put them over the top and get them over. Guys like Alex Riley, Brad Maddox, David Otunga, Drew McIntyre, Michael McGillicutty and Ted DiBiase Jr, could all benefit as far as persona goes. (Not that any have to become Flair clones.) But for Flair himself, maybe he manages one or some of them, maybe he just stays backstage.