Mike Tyson Full Chronology: from 1966 Birth to Monumental Ring Returns

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The wheels began coming off outside the ring after the Spinks victory. Tyson fired Kevin Rooney, severed ties with longtime manager Bill Cayton, and allied himself with promoter Don King. Without D’Amato's discipline, his training habits eroded. On February 11, 1990, in Tokyo, a 42-to-1 underdog named James "Buster" Douglas knocked Tyson out in the tenth round, dealing him his first career defeat.

Two years later, Tyson was convicted of rape in Indiana and sentenced to six years in prison. He served three years at the Plainfield Correctional Facility before his release in March 1995. During his time behind bars, Tyson converted to Islam, taking the name Malik Abdul Aziz.

His ring return generated massive financial returns. In 1996, he knocked out Frank Bruno to reclaim the WBC title, followed by a first-round victory over Bruce Seldon to capture the WBA belt. The redemption stalled against Evander Holyfield in November 1996, where Tyson was stopped in eleven rounds. Their June 1997 rematch ended in disqualification when Tyson bit off a piece of Holyfield's right ear, leading to a temporary license revocation by the Nevada State Athletic Commission.