Now he has reinvented himself again - hopefully for the last time - as the friendly face and folksy frontman for Iron Mike Productions.
On Friday night he'll make his promotional debut at the Turning Stone Resort Casino in Verona, New York, when Canada's Arash Usmanee (20-1) challenges IBF super featherweight champion Argenis Mendez (21-2) of Argentina.
"I'm thrilled to be bringing my first fight as Iron Mike Productions to Turning Stone and ESPN," Tyson said during an international media conference call last week.
"Upstate New York is very special to me and brings back nostalgic memories of when I was an amateur on the rise. I want to be there to guide my fighters as they take these same stepping stones in their quest for greatness."
When asked how much savvy he can pass on to the fighters he promotes, Tyson was brutally honest.
"Hey, I'm in no position to stop someone from hurting themselves; only thing I can tell them is what I experienced, how you can go crazy over that stuff," he said.
"Other than that, I can't do anything. I'm not a magician. I'm not a hit man. I can't make someone do anything. Only thing I can do is suggest.
"I'm not going to get on the phone and say I'm going to stop these guys from getting high and blowing their money.
"I don't know if I can do that. This stuff is bigger than me.
"I just know one thing - you're never going to hear my fighters say that Mike Tyson ever stole from them. And hopefully they will never end up like me when it's all over and say, 'Where's my money and my friends? Oh man, I'm a goner.' They won't have to do that stuff."
It seemed unlikely all those years ago when he strode the world stage like Gilgamesh, laying waste to everything around him, but today, at age 47, it sounds like Iron Mike has finally grown up.
Best of luck in your new venture, champ. It's good to have you back.
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