On June 28, 1997 – during a fight billed as The Sound and the Fury – the sight of enamel ripping through flesh sickened fight fans and left the sport at rock bottom.
Aged just 13, a desperately poor youth facing a bleak future, he had notched up 38 arrests and was a willing student in the dark arts of burglary and street robbery.
But his most heinous transgressions were to come when he was at his most rich and powerful.
Evander Holyfield had studied Tyson religiously but was almost flattened from the shorter man’s very first punch.
Holyfield saw the WBA champion dip to his left and expected a trademark left-hook from Tyson’s offensive textbook but the Brownsville bomber stunned him a right-cross.
That moment of genius was to be Tyson’s first and only moment of dominance. Holyfield used his s uperior height, strength and reach to frustrate and pummel his rival.
The illegal use of his head even opened up a raw gash on the convict that he was never to forget.
With 15 seconds of the seventh round remaining, Holyfield lunged forward and the pair cracked skulls once again with Tyson howling out in pain as he once again suffered at the head of the in-ring bully.
Holyfield tied-up, pushed around and prodded at Tyson until a barrage in the final seconds of the 10th round left him spark out on his feet but somehow upright.
But it took just seconds on the 11th for the referee to save Tyson from demolition.
The fallen hero had seven months to sit and stew on that result and performance, while abusing his mind and body with far more vigour than he was spending in the gym.
The roughhouse tactics Holyfield employed to disarm and embarrass the once impervious world champion were replayed on TV screens everywhere. Tyson could never face that shame again.