Lee Groves

10: Most historically significant upsets

5. Evander Holyfield KO 11 Mike Tyson I: Nov. 9, 1996, MGM Grand Garden Arena, Las Vegas, Nevada

For years Tyson vs. Holyfield represented the Holy Grail for boxing fans, not only because it matched two of the generation’s most dynamic and explosive big men but also because making it happen turned out to be a Herculean – if not Quixotic – task.

A fight between the two was first arranged for June 1990 but all that went up in smoke when James “Buster” Douglas produced the performance of a lifetime and stopped Tyson in 10 rounds. After Holyfield won the undisputed title with a one-punch knockout over Douglas, he and Tyson were set to fight in November 1991 but a rib injury to “Iron Mike” prompted a postponement. After the fight was rescheduled Tyson was charged with, then convicted of, rape, for which he served three-and-a-half years in prison.

Meanwhile, Holyfield lost the belts to Riddick Bowe and regained the WBA and IBF portions from “Big Daddy” a year later. Holyfield then lost them to Michael Moorer, after which he was diagnosed with a heart condition that forced Holyfield to announce his retirement. Holyfield later said that he was misdiagnosed.

Holyfield launched a comeback but he didn’t appear to be the same fighter. He out-pointed Ray Mercer over 10 bruising rounds, lost the rubber match to Bowe via eighth round TKO and stopped former light heavyweight and cruiserweight titlist Bobby Czyz in five.

On the other hand Tyson improbably regained his aura of invincibility after finishing his prison sentence. He destroyed Peter McNeeley in 89 seconds, crushed Buster Mathis Jr. in three rounds, regained the WBC title from Frank Bruno in three and, after being stripped of that belt for not facing mandatory challenger Lennox Lewis, he won the WBA strap by stopping Bruce Seldon in 109 seconds.

The combination of the 34-year-old Holyfield’s struggles and Tyson’s renewed destructiveness caused the pre-fight story line to adopt a prohibitive tone. The question wasn’t whether Holyfield would win or lose, it was rather if he would live or die. Holyfield allayed some of those concerns by passing a battery of medical tests but even after that few believed in “The Real Deal.” Tyson opened as a 25-to-1 favorite but by fight time they settled on 6-to-1. Of the 40 sports writers polled at ringside, only one – the Boston Globe‘s Ron Borges – picked Holyfield to win.

Fearing another one-round debacle, one local cable company unsuccessfully tried to employ a “pay-per-round” charge in which viewers would be charged $5 for every round the main event lasted.

They need not have worried, for those who pressed the “buy” button were in for the surprise of a lifetime.

Tyson came out with his customary charge and staggered Holyfield with his first right hand. But that initial success was followed by long stretches of frustration. The 6-foot-2½ inch Holyfield stood three inches taller than Tyson and his chiseled upper body carried phenomenal strength, an asset for which Tyson didn’t account. After muscling Tyson back onto his heels in the clinches, Holyfield often punctuated his physical dominance with intelligent counters. To everyone’s surprise Tyson couldn’t push Holyfield back nor could he intimidate him. When Tyson hit Holyfield after the first round bell, the challenger retaliated with his own punch.

“All you got to do is stay calm; you see everything,” chief second Don Turner told Holyfield. “You’re the bully in here, he ain’t the bully.”

The mystique and punching power that cowed so many others had no effect on Holyfield. Worse yet for Tyson, Holyfield proved he had plenty of his own power as a volley of blows in the final minute of round two jerked Tyson’s head from side to side. That combination enabled Holyfield to clear another crucial mental threshold, for not only was he stronger than Tyson, he showed he had more than enough clout to hurt him. From that point forward, everything snowballed.

Holyfield’s ability to out-speed Tyson in point-blank exchanges and to survive “Iron Mike’s” best stuff in round five chipped away at the champion’s psyche. Two more events in the sixth inflicted even more damage. First, an accidental butt opened a cut above Tyson’s left eye, then, 30 seconds after the crowd broke into its first “Ho-ly-field, Ho-ly-field” chant, Holyfield dropped Tyson with a short, jolting left uppercut to the chin. It was Tyson’s first trip to the canvas since Tokyo six years earlier and more than a few observers began experiencing flashbacks to that surreal night at the Tokyo Dome.

In rounds seven through nine Tyson was treading water strategically while Holyfield flawlessly executed his multi-layered fight plan. With 20 seconds remaining in the 10th a massive Holyfield right sent Tyson reeling toward the ropes and his follow-up volley had the champion on the edge of unconsciousness.

This time Holyfield didn’t hesitate. A nine-punch explosion – two jabs, a chopping right to the head, two hooks, a right cross, a right uppercut, a left hook and a final right hand – rendered Tyson helpless and caused referee Mitch Halpern to intervene at the 37-second mark of round 11. And with that, one of history’s most colossal upsets was burnished into the record books. 

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