Mike Tyson told his Hotboxin’ podcast that he once had to pay a fan £6.2 million after he broke his jaw because he wouldn’t stop pestering for an autograph.
Known for his furious temper in and out of the ring, Tyson said he repeatedly came into contact with fans who asked for his signature.
"I was that guy, trippin', hitting people because they're f***ing with me too much for autographs," said Tyson.
"I f***ing knocked them out or would break their f***ing jaw.
"I started signing those cheques, and that's what broke my spirit.
"These guys were getting $4m [£3.1m], $8m [£6.2m], I don't even know these guys - who are these guys?"
Tyson, who became the youngest ever world champion at 20 in 1986, has never strayed far from infamy, frequently adorning the front pages for a myriad of scandal and misbehaviour.
One such incident came as a result of his ownership of a Bengal tiger, who attacked a trespasser who had jumped the fence of Tyson's property. Tyson had to pay the individual £200,000 after the feline destroyed the trespasser's hand.
Tyson: "You can't believe what they can do to human flesh - I had no idea.
"I was foolish then, there is no way you're going to domesticate these cats 100 per cent, there's no way that's going to happen."
The boxer, who secured 44 knockouts in his 50 wins, shockingly lost his title to James Buster Douglas in 1990, and in 1992, was convicted for three years for the rape of beauty pageant contestant Desiree Washington.
He was jailed again in 1999 for assaulting two men, but not before he bit off part of Evander Holyfield's ear in 1997, which saw him banned from the sport.
Although the 'Baddest Man on the Planet' retired in 2005, with a 50-6-2 record, he is set to make his return to the ring in an exhibition bout with Roy Jones Jr on November 28.
Jones is three years Tyson's junior at 51, and comes into the fight with an impressive 66-9 record of his own, with 47 KOs.
Love him or hate him, Mike Tyson is an iconic figure in the sporting world, and his comeback fight is guaranteed to be one to watch.
- Manny Pacquiao confirms Conor McGregor fight is on
- Floyd Mayweather vs Logan Paul simulated
- 'AJ will beat Fury as he's a better all-round boxer'