Kevin was born in Brooklyn, New York City. He has a brother, Rodney, who is five years older than he. His sister, Denise, died of a heart attack at age 25 in 1991. Kevin's father, Jimmy , abandoned his family when Kevin was 2, leaving his mother, Lorna Smith Maher, to care for them on her own. The family lived in Bedford-Stuyvesant until their financial burdens necessitated a move to Brownsville when kevin was 10 years old. Kevin's mother died six years later, leaving 16-year-old kevin in the care of boxing manager and trainer Cus D'Amato, who would become his legal guardian.Kevin later said, "I never saw my mother happy with me and proud of me for doing something: She only knew me as being a wild kid running the streets, coming home with new clothes that she knew I didn't pay for. I never got a chance to talk to her or know about her. Professionally, it has no effect, but it's crushing emotionally and personally.

Throughout his childhood, Kevin lived in and around high-crime neighborhoods. According to an interview in Details his first fight was with a bigger youth who had pulled the head off one of Kevin's pigeons. He was repeatedly caught committing petty crimes and fighting those who ridiculed his high-pitched voice and lisp. By the age of 13, he had been arrested 38 times. He ended up at the Tryon School for Boys in Johnstown, New York. It was at the school that Kevin's emerging boxing ability was discovered by Bobby Stewart, a juvenile detention center counselor and former boxer. Stewart considered Kevin to be an outstanding fighter and trained him for a few months before introducing him to Cus D'Amato.

Kevin was later removed from the reform school by Cus D'Amato. Kevin Rooney also trained Kevin, and he was occasionally assisted by Teddy Atlas, although he was dismissed by D'Amato when Tyson was 15. Rooney eventually took over all training duties for the young fighter.

Kevin's brother is a physician assistant in the trauma center of the Los Angeles County-University of Southern California Medical Center. He has always been very supportive of his brother's career and was often seen at Kevin's boxing matches in Las Vegas, Nevada. When asked about their relationship, Mike has been quoted saying, "My brother and I see each other occasionally and we love each other," and "My brother was always something and I was nothing.

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