Thirty-seven years after rewriting boxing's record books by becoming the youngest heavyweight champion in history at the age of 20, Tyson is plotting another ambush.
He has been hired to help train mixed martial arts star Francis Ngannou (37) ahead of the Cameroonian fighter's money-spinning heavyweight boxing showdown with Britain's Tyson Fury (35) taking place in Saudi Arabia on October 28.
In the eyes of bookmakers at least, the odds are stacked against Ngannou, who will climb into the ring against the undefeated Fury next month having never boxed professionally. Ladbrokes have installed Fury as a 1/10 favourite; Ngannou a 6/1 underdog.
Yet as the 6ft 4in (1.93m), 264lb (120kg) Ngannou unleashes an array of punches on his heavily padded trainer, Dewey Cooper, the mood is anything but pessimistic.
Occasionally, Tyson, standing to one side, will intervene to correct a movement or suggest a subtle tweak. Ngannou, a long-time fan of the American boxing icon, relishes each suggestion.
"He comes from time to time to lend a hand, to give his expertise," Ngannou told a group of reporters during a workout.
"I had specifically asked for him to train me four years ago, long before this fight was announced, the first time I met him.
"He has something inspiring, something motivating. If I could ever have just a tiny piece of what he has, boxing would be very easy for me."
Ngannou has taken a long and unconventional road to his boxing debut.
He first took up boxing in his 20s in his native Cameroon, later moving to Paris hoping to forge a professional career.
But he would ultimately end up in the rough and tumble world of mixed martial arts, eventually becoming the UFC's heavyweight champion and one of the circuit's biggest stars, winning 17 of his 20 fights including 12 by knockout.
'Nervous? He should be'
Whether Ngannou's skills in the octagon will translate to the boxing ring remains to be seen. Tyson, however, says he has been impressed by what he has seen during Ngannou's training camp.
"We're in a good position over here," the softly-spoken Tyson tells reporters.
"He's very dedicated, he put forth the effort and I think people will be pretty much more surprised than they anticipated.
"This is the biggest fight in boxing right now, in all sports. In fact, there's no doubt about it. It'll be the biggest upset in the history of entertainment. I think I bring him confidence this could be accomplished."
Should Fury feel nervous? "I don't know if he's nervous or not," Tyson said. "But he should be."
The size of the task facing Ngannou however is undeniably gargantuan.
At 6ft 9in, the skillful Fury (33-0-1, 24 knockouts) will take a sizeable height and reach advantage into the ring against Ngannou, where no titles will be at stake.
The British self-styled "Gypsy King" has repeatedly demonstrated his near-superhuman capacity to absorb punches as well as his ruthless instinct for dispatching opponents.
Those in Ngannou's camp however are adamant that the Cameroonian has a puncher's chance.
Carlos Takam (42), the Cameroon-born heavyweight who has been training alongside Ngannou in Nevada, says all bets will be off when the bell sounds for the first round in Riyadh.
"Anything can happen in the heavyweight division," said Takam, who upset France's 2016 Olympic superheavyweight champion Tony Yoka (31) in March this year.
"We're talking about behemoths who can hit you with the full force of 120 kilos," said Takam. "When that happens, you fall, and you don't get up, even if you're stronger. Don't be surprised if something happens during this fight."