Mike Tyson was one of the baddest boxers ever and up to his point of imprisonment for rape charges, he had one loss on his record. Tyson entered the ring with a ferocity that was and still is unmatched. The youngest to ever be named heavyweight champion of the world, Tyson lost three years of his prime due to a rape charge. Once he came home, Tyson lost a part of his soul and was never the same fighter. Jail tends to do that to people.

What could've been: The heavyweight division died when Mike went to jail. Guys like Evander Holyfield and Lennox Lewis didn't have the same star power Tyson had. He was a polarizing figure that made headlines. Being behind bars made him even more of a crazy person. Tyson would've fought Holyfield and Lewis while in his prime, and probably could've inspired a new generation to become heavyweight champions.