One of the greatest upsets in the history of heavyweight championship boxing. Holyfield’s promoter, Dan Duva of Main Events, said he earned $230,000 at Las Vegas sportsbooks after betting $15,000. Oddsmakers installed Tyson as a 25-to-1 favorite he closed at 6-to-1. He scored a first-round TKO of Bruce Seldon two months earlier. Tyson, on the other hand, had torn through the competition (albeit light opposition) in four fights since leaving prison, recapturing the heavyweight crown along the way. Holyfield failed to impress against Czyz. “Real Deal” was 3-3 in his last six bouts entering the Czyz matchup and was considered well past his best days. Those were the words of Showtime analyst Bobby Czyz, the man Holyfield fought in a tune-up six months prior to his championship clash with Tyson, seconds after referee Mitch Halpern halted the contest in Round 11 as Holyfield battered Tyson along the ropes. It is the most unbelievable thing I have ever been privileged to witness. Maybe it was because you knew Don King loomed and that scoring shenanigans were possible.Ĭoppinger: “I can’t believe what I’m seeing. Pugmire: I watched that bout live from the kitchen of a friend’s friend - I ranked very low on the invitation list, I guess - and from what I can recall from that evening, it seemed the fight was much closer than it was. After a second consecutive loss to Holyfield, Tyson’s corner was a revolving door. When Tyson faced Holyfield in the rematch, Richie Giachetti was the chief second. He’s best known for being trained by Cus D’Amato, but after his death, there were so many different faces throughout the years. With Tyson, it’s hard to keep track of who manned his corner. It was Jay Bright, who led Tyson’s corner following his release from prison. Looking back, what aspect of the fight had you forgotten about?īartholomew: Holyfield’s gigantic trapezius muscles! The mid-‘90s were a more innocent time in terms of the boxing public’s skepticism over boxers’ use of banned substances, but Holyfield, who was linked to PED scandals later in his career, raises an eyebrow or two in this fight.Ĭoppinger: Just who Mike Tyson was trained by. But when Tyson injured his ribs weeks away from fight night, it was postponed. Still, the fight was set to push forward. Two months before they were set to step into the ring, Tyson was indicted on rape charges. Tyson would be the challenger after Holyfield knocked out Douglas. “Iron” Mike was originally scheduled to fight Holyfield in June 1990 in Atlantic City, but Buster Douglas canceled those plans in a monumental upset four months earlier.Īgain, they were set to meet, this time in November 1991 in Las Vegas. Still, something was missing: a fight with Holyfield. Mike Coppinger: Tyson was one of the biggest stars in sports and was champion yet again after knocking out Frank Bruno following a prison stint. Even while facing long odds against Tyson, Holyfield was considered among the handful of fighters with hopes of beating “Iron Mike,” and Holyfield’s trilogy against Bowe and win over Foreman still meant zilch to the boxing world, which considered him a 25-1 underdog against Tyson when the fight was made and a 6-1 underdog on fight night. But regardless of their separate ring accomplishments, they still hadn’t proven it against each other. Even before Tyson’s loss to Buster Douglas and the time he spent in federal prison for a 1992 rape conviction, Holyfield was considered a rising threat to Tyson’s throne. Rafe Bartholomew: Tyson-Holyfield was the answer to a question boxing fans had been pondering for more than half a decade.īoth Tyson and Holyfield had proved themselves before their first fight - Tyson with his dominant rise through the heavyweight ranks in the late ‘80s, and Holyfield with his fights against Riddick Bowe and George Foreman, among others. Following a trilogy with Riddick Bowe, Holyfield confronted a chance to tie Muhammad Ali by winning a heavyweight belt for the third time. Holyfield had beaten James “Buster” Douglas after that colossal upset of Tyson, but Holyfield had repeatedly heard, “You’re just holding Tyson’s belt” afterward. Those foes allowed Tyson to beef up his knockout reputation, but by finishing each of them before the end of the third round, he deprived himself of a real test. After spending more than three years in prison after being convicted for rape, Tyson returned to the ring and fought four lackluster opponents. Lance Pugmire: Tyson was looking to reassert himself with a definitive heavyweight-title triumph. What was at stake for both Tyson and Holyfield going into the fight? In several ways, the bout came to define both men’s careers, and The Athletic’s boxing staff recently made time to rewatch and re-evaluate this unforgettable night in boxing history. Less than two years after his release, Tyson finally faced Holyfield in Nov.
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