A Tale Of Two Comebacks: The Legend And Legacy Of Mike Tyson Vs. Evander Holyfield

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With thick plates of muscle and hands as lethal as any heavyweight in the business, Mike Tyson was becoming the monster that boxing fans had been craving. In just his first year of fighting, Tyson had amassed 15 wins, all in dominant fashion. In 1986, his second year as a pro, Tyson pummeled Trevor Burbick to win the WBC heavyweight championship. By 1987, Tyson had all the gold at just 20 years of age: the WBC, WBA, and IBF world championships were in his possession and many boxing pundits wondered what could derail the freight train of terror that he was inflicting in the squared circle. 1988 saw Tyson face his toughest test in the disputed lineal champion Michael Spinks. Within 91 seconds, Tyson dispatched of Spinks and was crowned the universally recognized undisputed heavyweight champion. No one could beat Tyson but Tyson himself, but by 1990, that prophetic statement would come to fruition.

With his marriage to Robin Givens disintegrating, and a drug problem — specifically with cocaine — beginning to emerge, Tyson started to unravel. It didn’t help that Cus D’Amato, Tyson’s trainer and father figure, had died several years earlier and many attribute his loss to Tyson losing sight of his career, goals, and responsibilities. In 1990, Tyson faced the underdog Buster Douglas, who many pegged to lose within the first round as many of Tyson’s opponents did. The fight, held in Tokyo, produced one of the biggest upsets of all-time. Although Tyson knocked Douglas to the canvas in the eighth round, Douglas fought back and propelled a brutal combination of strikes to Tyson’s head in the 10th — Tyson didn’t answer the count.

Tyson’s personal life had caught up to him in he ring and he had lost the undisputed championship amidst reports that he had undertrained for the bout and was physically and mentally unprepared to defend his crown.

…It’s How Fast You Get Back Up

With his personal and professional life on the ropes, Tyson attempted to get things back on track. In his first two fights after the Douglas defeat, he quickly disposed of Henry Tillman and Alex Stewart with his trademark first round assaults. Meanwhile, Evander Holyfield — a fan-favorite and one of the best heavyweights in the world — defeated Buster Douglas for the undisputed crown in Douglas’ first title defense. After Tyson’s two successive wins following the upset, a 12-round title eliminator bout was set against dangerous power puncher Donovan “Razor” Ruddock. Ruddock was coming off an impressive win over Michael Dokes, in which he used a clever left uppercut-turned-straight to almost knock Dokes head clean off, as well as a first-round win over Mike Rouse. During this time, Holyfield was set to defend his titles against George Foreman, but the WBC employed legalities to block the bout stating they wanted the champ to fight Tyson first.

Tyson and “Razor” Ruddock fought in March of 1991. Their first fight was supposed to occur while Tyson was still champ, but he had to withdraw from the bout; this time it was the number one and two contenders battling for a shot at Evander’s title. Tyson knocked Ruddock down twice in the fight although one knockdown was actually a trip but still, referee Richard Steele counted it as a fall. Tyson continued to punish “Razor” with lethal combinations, and in the seventh round, he unloaded a six-punch volley that dazed and stumbled his opponent — Steele stepped in and stopped the bout. It was a controversial stoppage, because Ruddock had not been downed and he seemed capable of continuing. The decision sparked a post-fight brawl and Steele had to be escorted from the ring.

Because of the controversy, Ruddock and Tyson would meet one more time to finally settle their score. This time, Tyson would win by unanimous decision and the number one contender was scheduled to face champ Evander Holyfield on November 8, 1991. Tyson wouldn’t get to the bout though, as a training injury to his rib cartilage caused him to withdraw from the fight. Before their fight could be rescheduled, Tyson hit another roadblock: prison.