In 1990, Holyfield beat Seamus McDonaugh by a knockout in four, and was by then, ranked number 1 among the world's Heavyweight challengers. By then, however, what is considered one of the biggest upsets in sports history had happened, when James Buster Douglas dismantled Tyson in 10 rounds in February at Tokyo to become the world's Heavyweight champion. And so Holyfield had no choice but to challenge Douglas instead. Douglas weighed 246 lbs for this fight after weighing 231 lbs against Tyson. Holyfield became the undisputed Heavyweight champion of the world when he knocked the unmotivated and undertrained Douglas out in three rounds with a single right cross.
In his first defense, he beat former and future world champion George Foreman by a decision in 12, and then a deal was signed for him to defend his crown against Tyson in November of 1991. Tyson was convicted of the rape of Desiree Washington and sentenced to six years in jail, and the proposed fight did not come off. Holyfield made the next defense in Atlanta against Bert Cooper, against whom he had to recover from the first knockdown suffered in his career when Cooper floored him in round three, but he recuperated and knocked Cooper out in round seven.
In his first fight of 1992, he faced former world Heavyweight champion Larry Holmes, and retained the belt, once again by unanimous decision. But for his next fight, he wasn't as lucky: In the beginning of a trilogy of bouts with Riddick Bowe, he suffered his first defeat when Bowe won the world title by a 12 round decision in Las Vegas. Round 10 of that bout was named the Round of the year by Ring Magazine.
He began 1993 by beating Stewart in a rematch, but this time over the 12 round distance. Then came the rematch with Bowe. In what is considered by many historians as one of the most bizarre moments in boxing's history, Holyfield had been taking solid jabs to the face from Bowe in round seven, when everyone in the crowd got off their feet and many people started to run for cover and yell. Holyfield took his eyes off Bowe for one moment and then told Bowe to look up to the skies. What they saw was a man in a parachute flying dangerously close to them. The man landed inside the ring, but tripped into one of the ring's corners, where he was beaten by members of Bowe's entourage. Bowe's pregnant wife, Judy, fainted and had to be taken to the hospital from the arena. Twenty minutes later, calm was restored and Holyfield went on to recover his world heavyweight titles with a close 12 round majority decision. The guy who parachuted down to the middle of the ring became known as The Fan Man and the fight itself became known as the Fan Man Fight.
