James “Buster” Douglas began boxing professionally in the 1980s and was considered a talented fighter, but it was believed he lacked the motivation to become a champion. By contrast, Tyson had become the youngest heavyweight champion in boxing history when he defeated Trevor Berbick by knockout in 1986, when he was just 20 years old.
Nicknamed “Iron Mike,” Tyson intimidated other boxers with his fast, powerful punches. Going into the February 11, 1990, match with Buster Douglas, Tyson seemed invincible and was considered a 42-1 favorite to win. However, from the start, Douglas managed to dominate the fight. He was said to have been motivated by the pain of his mother’s death several weeks before the match. Tyson, on the other hand, didn’t seem to have his heart in the fight, although he knocked Douglas to the ground at the end of the eighth round. Douglas was able to get back up and went on to knock out Tyson and win the fight in the 10th round of the scheduled 12-round match. His victory was considered one of the biggest upsets in boxing history.
Douglas’s reign as heavyweight champ was short-lived. After defeating Tyson, he fought Evander Holyfield in October 1990. Douglas lost the fight in three rounds and afterward announced his retirement from boxing, although he staged a brief comeback in the late 1990s.
The loss to Douglas was the beginning of a long, downward spiral for Tyson: In 1992, he was convicted on rape charges and served three years in prison. In 1996, he won the World Boxing Council title but lost to Evander Holyfield later that year. During a 1997 rematch, Tyson bit Holyfield’s ear and was temporarily banned from boxing. In 2002, after instigating a pre-fight brawl with Lenox Lewis, Tyson’s Nevada boxing license was revoked. The match was moved to Memphis, where Tyson lost the fight. In 2003, despite having earned hundreds of millions of dollars, he declared bankruptcy and in 2006, he was arrested on drug charges.