Besides his vicious punches, Tyson is infamous for his behavior inside the ring and out. He spent three years in prison for rape in 1992. According to NPR, Tyson was fined $3 million for biting off a piece of Holyfield’s ear during their heavyweight title encounter in 1997. However, it didn’t end the boxing legend’s erratic behavior. In 2007, Tyson had to spend 24 hours in prison, serve three years of probation, and undergo 360 hours of community service for felony drug possession (via Sportscasting). “The man I’ve become? Baddest Man on the Planet? I wasn’t half the man I ever thought I was,” he told The Guardian. “I’m a pig. I have this uncanny ability to look at myself in the mirror and say: ‘This is a pig. You are a f**king piece of s**t’.”

After becoming a top-notch fighter, though, Tillman too hit rock bottom. According to the Los Angeles Times, he was imprisoned for drug use, grand theft, battery, and armed robbery during his teenage years. In 1994, he was sentenced to 32 months in prison after pleading guilty to credit card fraud. Seven years later, Tillman was found guilty of murder and voluntary manslaughter. Per the Los Angeles Times, Tillman fired a .38-caliber revolver outside the Townhouse nightclub in 1996, killing one and severely injuring another. He was released in 2002, but in July 2004, Tillman was sentenced to 37 months in prison after he pleaded guilty to federal identity theft charges (via ESPN). Per Boxing News, he became a trainer to IBF world heavyweight champion Charles Martin in 2016, and runs Henry Tillman Championship Boxing Club in the Los Angeles area.

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