Mike Tyson was on top of the world. He was the youngest professional boxer ever to be named heavyweight champion. He was the most feared and most popular boxer in the world. Tyson made north of $400 million in his career and wound up filing for bankruptcy. Tyson was asked recently by legendary sportscaster Jim Gray what happened to all the money, and Tyson candidly provided an answer.

Mike Tyson’s legendary boxing career

Mike Tyson was simply dominant in the boxing ring. At the age of 20, he became the youngest boxer ever to win a heavyweight title. Not only did Tyson become a heavyweight champion, he did it in impressive fashion.

Tyson won the first 19 fights of his professional career via knockout. Twelve of those knockouts came in the first round. He was victorious in his first 37 professional bouts. Tyson successfully defended his title nine times before his shocking loss to James ‘Buster’ Douglas in February of 1990. He was convicted of rape in 1992 and served three years, getting out on parole.

Tyson returned to the boxing ring in 1995. He began his comeback against Peter McNeeley. Tyson made quick work of McNeeley and improved his overall record to 42-1. After the McNeeley fight, Tyson went 8-5 in his final 13 fights. He suffered consecutive losses to Evander Holyfield, and lost his last fight to Kevin McBride in June of 2005. Tyson finished with a record of 50-6, getting 44 wins by knockout.

Tyson’s problems outside the ring

Mike Tyson spent three years in prison during the peak of his boxing career. He was 41-1 after defeating Donovan Ruddock in back-to-back bouts before he was sentenced to 10 years in prison after being convicted of rape in 1992. According to The New York Times, a judge suspended the last four years of his sentence. He was released after serving less than three years.

According to Business Insider, Tyson earned approximately $300 million during the height of his boxing career. He filed for bankruptcy in 2003. He had lost all his money and was $23 million in debt.

Tyson had also been arrested multiple times on drug charges. He had checked himself into a treatment center to get help. In a 2006 ABC News story, Tyson said he was diagnosed as being bipolar and he had low self esteem. “It’s not working out too well,” he said. “I get knocked down, but I keep getting back up, being Mike and dealing with who I was in the past … it’s just not working out too well.”

What happened to all of Mike Tyson’s money?

In a recent episode of Hotboxin’ With Mike Tyson, longtime sportscaster Jim Gray was in the studio with co-hosts Mike Tyson and Eben Britton. The three were speaking about old times and reflecting on both Gray’s and Tyson’s careers. Gray then put on his interviewer cap and asked Tyson a question. What did you do with all your money? Tyson answered candidly.

“Hey, I just gave a lot of it away,” he said. “I had a lot of fun. I just did what I wanted to do and I had a lot of fun. When I was a kid I had a really good time. I was all over the world. I was with awesome people, wealthy people. It almost felt bad. It felt so good, it felt wrong. You know, you’re wrong to have all this ecstasy, have all this sensation, have all this fun, and all this wealth. It just felt wrong. It was awesome.”

Tyson said he has no regrets about how he spent that money. “No, I have no regrets,” he said. “Maybe some, but no. As I get older, I say no. When I was younger, I was saying maybe I should have some regrets. My life is the way it’s supposed to be now. It’s preparing me for grander things. I’m surprised I’m not dead from the way I lived my life.”