Mike Tyson was once one of the most feared boxers on the planet, but his weakness for women -like supermodel, Naomi Campbell- apparently got in the way…according to his former friend of many years/ex-manager, Rory Holloway.

Instant Attraction:

As quiet as it’s kept, Robin Givens wasn’t the only woman that Tyson was diggin’ back in the day, he was once madly in lust with Naomi and they didn’t hide they’re relationship from the public. As Tyson became the heavyweight champ in the ring, obviously his money grew, as well as his choices in women. Despite being labeled as a “bad boy”, it didn’t stop the ladies from wanting to meet him. This was reportedly the case when he met Campbell in New York city at a Russell Simmons’ party.

Tyson’s manager, Holloway, was there the night that Tyson and Campbell met and BOY did he have a story to tell! In Holloway’s book, Taming the Beast: The Untold Story of Mike Tyson, he shared how in the early days of Tyson’s career, although he was technically his good friend and manager, he often served as a ‘chaperone’ to Mike to ensure that he stayed out of trouble….

Ex-Manager Details Their Alleged Freaky First Encounter

Apparently, Naomi didn’t abide by the boundaries Lisa Lisa & The Cult Jam once sang, when Lisa pondered, “I wonder if I take you home would you still make me love baby/Because I need you tonight.” How so? Because according to Holloway, on the night that Campbell and Tyson met, he couldn’t believe that Tyson was mingling with Naomi, who was the hottest model in the game. The British beauty was the talk of the town and like so many other women, she, too, was attracted to Mike Tyson.

Rory Holloway: “I was there to keep Mike out of trouble, doing my usual babysitting job, and when I looked over, he was talking to this girl,” Holloway wrote. I had to rub my eyes. I mean, the most exciting thing at that time was Naomi Campbell. She was wild and vivacious, with these legs that went on for days.”

Like Tyson, Campbell was rich, famous, and wild. Holloway revealed how on the night Tyson and Naomi first met at Russell Simmons’ party in New York, he was given the task of holding their drinks as Tyson and Campbell got to know each other in the bathroom stall…yep you read that right. To prevent other guests from entering the bathroom, Holloway said he blocked the entrance and told people that the bathroom was taken. As minutes passed, unknown to Holloway, Mike and Naomi were doing more than just talking:

Holloway: “Minutes go by and it’s getting uncomfortable. I finally crack open the door, ‘C’mon Mike.’ I see Naomi. She’s up on the toilet, heels and long legs spread, skirt hiked up, and Mike’s pumping away.”

Naomi Went Ratchet On Tyson After He Cheated?

To many, it was apparent that Naomi and Mike had a strong attraction for each other. That night of the Simmons’ party led to many other nights as the two became a ‘thing.’ However, their relationship didn’t last though, but it definitely had it’s wild times. Holloway says Tyson had a weakness for women at that time, so not even the beautiful Naomi Campbell could keep his attention long because he reportedly began to cheating on her. BUT that’s when Rory Holloway says Naomi turned it ALL the way up:

Holloway: Mike would be clubbing and he’d come outside and she’d be standing in six-inch heels on the hood of his car, putting dents in it. One day Naomi came over to the Vegas Hilton – we could hear Mike messing around with girls in the other room. So she gets out on the balcony. It was 29 floors up but she went from one balcony to another like ‘Catwoman.’

At that time, Tyson had just become the heavyweight champ. But according to Rory, that couldn’t keep Campbell around and she reportedly grew tired of Tyson’s cheating and climbing up on balconies like ‘Catwoman’ to bust him, so Holloway says they eventually broke up.

Why Did Tyson’s Ex-Manager Decide To Talk Decades Later?

As one of the original members of Mike Tyson’s team, Holloway prides himself on being one of the people that helped guide Mike toward becoming the youngest Heavyweight Champion in boxing history, at the age of 19 years old. Despite the long friendship that dates back to them being teenagers, The Mirror shared why Holloway decided to drop these bombshells about his former main man, Tyson:

‘[Holloway] decided to talk after his son was tormented over claims he blew Tyson’s millions. Holloway denies those allegations, and insists Tyson was his own boss and was simply reckless with his money.’

Ex-Manager Still Respects Tyson

Even though many parts of the book paints Tyson in an unfavorable light, Holloway maintains that Tyson is a good man with a big heart.

He was very generous. Whether it was $5 or $500,000, he gave it to anyone with a sob story. He took care of family and friends, paid mortgages and bills. But somewhere along the way he got lost.

Well damn! Tyson’s manager said a mouthful. Thoughts ILOSM fam?’