A Look Back At Mike Tyson's Whirlwind Fling With Model Naomi Campbell

Mike Tyson's dating history includes several famous women, one of whom is supermodel Naomi Campbell. The pair had a whirlwind fling that began in the late 1980s while he was a rising boxing star and she was a blossoming top model who has amassed an $80 million net worth. While their relationship wasn't highly publicized at the time, it appears to have been chaotic from the very start.

The pair reportedly first crossed paths in 1987 at a party held by underwear designer Fernando Sanchez. However, their first encounter was not very friendly, as British philosopher A.J. Ayer allegedly had to come in between Campbell and Tyson during a heated exchange. It's unknown why they were bickering, but Campbell was said to have walked away from that meeting without further incident. The two would again run into one another at another party held by music producer Russell Simmons. That engagement was likely much more pleasant, with a pal of Tyson's even claiming it turned steamy.

Mike Tyson's former manager, Rory Holloway, attended the event that ultimately brought the athlete and Naomi Campbell together. According to his October 2014 book, "Taming the Beast: The Untold Story of Mike Tyson," Holloway witnessed Tyson speaking with the runway icon. This time around, the two seemed to be drawn to one another, leading them to sneak off to a nearby bathroom.

Holloway wrote in the book, "Next thing I know, Naomi's following him in there. Holy s***. Guests are walking up. 'Bathroom's taken,' I'm telling them. Minutes go by, and it's getting uncomfortable." Holloway claims that when he went inside the restroom to retrieve Tyson, he found him and Campbell in a sexual position. It's unsure if the pair left together, but that was certainly not the last time Campbell and Tyson had a newsworthy moment that was kept under wraps.

During a September 2020 episode of her "No Filter With Naomi" series, the Vogue cover star sat down with comedian Chris Rock. During their chat, the two went down memory lane, and the subject of Naomi Campbell and Mike Tyson's tryst came up. Rock recounted a shocking story of Tyson pushing Campbell, now a mother of two, out of a moving car. According to Rock, the former world heavyweight champion became enraged when his lover gave her number to another man.

While Campbell would not confirm nor deny the story, she suggested that she may have been the one to get physical, asking, "You sure it wasn't me that pushed him? That's if I even got in the car with him ... It's a good thing we're all grown-ups today, and we're family ... It's nice to see him blossom. Those were fun times in New York ... can never go back to those." Tyson has also acknowledged their good times together, crediting Campbell with introducing him to the late fashion designer Gianni Versace, whom he was a big fan of early in his career. Though it's unclear exactly when their relationship fizzled or if the car tale truly happened, their parting ways may have been for the best.