By Boxing Insider Staff

Former undisputed heavyweight champion Mike Tyson appeared on comedian Theo Von’s “This Past Weekend” podcast, where the 59-year-old former titleholder grew visibly emotional discussing his late mentor Cus D’Amato, offered unfiltered recollections of his past struggles with cocaine addiction, and recounted a story about catching actor Brad Pitt at his home during his marriage to actress Robin Givens.

Tyson Breaks Down Recalling Cus D’Amato

Asked by Von what period of his life he would most want documented on film, Tyson did not hesitate.

“It’d be when I first met my mentor Cus D’Amato,” Tyson said.

D’Amato, the Catskill, New York-based trainer who previously guided Floyd Patterson and Jose Torres to world titles, took in Tyson as a 13-year-old after meeting him at the Tryon School for Boys, a juvenile detention facility in upstate New York. D’Amato became Tyson’s legal guardian following the death of Tyson’s mother in 1982 and trained him until D’Amato’s own death in November 1985, roughly a year before Tyson became the youngest heavyweight champion in history.

“Started boxing, started changing my life. Then I meet him. That’s the part I wish you could come back to,” Tyson said on the podcast.

When Von asked how Tyson knew D’Amato loved him, the former champion’s voice cracked and he covered his face with his hand.

“I had somebody I loved and they loved me,” Tyson said.

Tyson explained that D’Amato shielded him from criticism during his amateur years, with Von noting that the young Tyson would attack anyone who spoke negatively about him. Visibly agitated by the memory, Tyson then asked Von to change the subject.

“Then why you having me talking about this bullshit? Stop,” Tyson said.

Tyson on Hardship and Becoming Champion

Later in the conversation, Von asked Tyson whether he would have become heavyweight champion of the world had he received the kind of stable childhood most children need. Tyson rejected the premise outright.

“I don’t want that. Stay away from me. Keep that shit away from me. I like to suffer,” Tyson said. “I love to suffer. I don’t want no good time. I like being out of my comfort zone.”

Pressed by Von on whether a more conventional upbringing would have produced the same fighter, Tyson answered bluntly.

“No. The heavyweight bitch of the world. I know I’d be wearing slippers during the day probably,” Tyson said.

Cocaine Stories

Elsewhere in the appearance, Tyson described episodes from his well-documented history with cocaine use, which he has discussed publicly on multiple occasions over the years, including in his 2013 autobiography “Undisputed Truth.”

Tyson told Von he once stayed awake for four consecutive days during a bender, with the drug causing scabs and bleeding inside his nose. He said he was instructed by his supplier to use more cocaine to numb the pain.

“I took a hit and wow, that feels better. I never knew. I just took a hit and numbed it up. It wasn’t numb anymore. It started bleeding. I have to take another hit to numb it up,” Tyson recounted.

Tyson also recalled going to a personal physician seeking help to quit, only for the doctor to ask Tyson for some of the drug. The former champion said he later checked into a rehabilitation facility and handed over his remaining supply to a staff member, who Tyson alleged kept the drugs for himself.

“I gave him the coke, my last coke. I said, ‘Here, got some coke.’ The motherfucker took my coke,” Tyson said.

The Brad Pitt Story

Tyson also revisited a long-circulated story involving actor Brad Pitt and Tyson’s first wife, actress Robin Givens, whom Tyson married in February 1988 and divorced in February 1989. Givens starred in the ABC sitcom “Head of the Class” from 1986 to 1991.

“Me and my wife were going through a divorce. We might get back, but we were still f*cking. We were fighting in the paper, then we’d f*ck,” Tyson told Von.

Tyson said he went to the home he shared with Givens and found Pitt there.

“One day I went over the house. She wasn’t home. Then driving up the road with the BMW that I bought her, she had somebody. I thought it was one of her friends from Head of the Class. It wasn’t. It was some motherf*cker Brad Pitt trying to get some head,” Tyson said.

Pitt and Givens dated briefly in 1988 and early 1989, a period that overlapped with Tyson’s separation from Givens. Pitt confirmed an encounter with Tyson during that period in a 1999 Rolling Stone interview.

Tyson’s Recent Activity

Tyson last fought professionally on November 15, 2024, losing a unanimous decision to Jake Paul over eight two-minute rounds at AT&T Stadium in Arlington, Texas. The Netflix-streamed event drew 108 million live viewers globally, according to figures released by the streaming platform.

Tyson’s professional record stands at 50-7 with 44 knockouts. He held the WBA, WBC and IBF heavyweight titles between 1986 and 1990.

The full Theo Von episode is available on the comedian’s “This Past Weekend” podcast channels.