In the 1980s, two names towered over everything: Mike Tyson, the youngest and most feared heavyweight champion in history, and Michael Jackson, the biggest pop star the world had ever seen. On paper they had nothing in common. They became real friends anyway.
The first time they met, around 1989 after one of Michael’s concerts, Michael did not even recognize the most feared man on the planet and asked where he knew him from. It stung Tyson’s pride at first, but Michael meant nothing by it and soon invited him to hang out. That awkward start grew into a friendship that lasted until Michael died in 2009.
Here is what surprised Tyson the most. Like almost everyone, he had assumed Michael was exactly what the public saw, a shy, soft-spoken, almost childlike figure. A real-life Peter Pan who floated above the normal world and did not know much about it.
He was wrong, and he says so himself. The more time Tyson spent with him, the more he realized Michael was sharp, streetwise and far more worldly than that gentle image let on. In Tyson’s telling, the King of Pop was even a smooth operator when it came to women, nothing like the naive innocent the world pictured. It flipped Iron Mike’s whole idea of who Michael was.
Hear Tyson tell it himself:
Mike Tyson Says Michael Jackson Was A ‘Player’ With Women
Coming from Tyson, that is quite a turnaround. He went from barely respecting Michael to being impressed by how clever and self-aware he actually was.
And Michael moved in those circles with ease. He crossed paths more than once with Muhammad Ali too, another giant of the boxing world. The gentlest-seeming man in entertainment was perfectly at home around the toughest men on the planet.
That is the thread running through all of it. The Michael Jackson the world thought it knew, the shy figure behind the sunglasses, was only ever one slice of the real person. Behind the soft voice was a sharp, funny, wide-awake man who knew exactly what he was doing.
Press play and hear Iron Mike describe the Michael Jackson almost nobody got to meet.