From Taming Tyson To Bashing Buster, Evander Holyfield’s Best Nights In Boxing

Holyfield's extraordinary career featured some incredible fights
14:00, 25 Oct 2020

Today marks 30 years since Evander Holyfield, undisputed cruiserweight champion, won his first titles in boxing’s marquee division after he battered a hopeless James ‘Buster’ Douglas inside three rounds in Vegas to claim the WBA, WBC, IBF, The Ring and lineal Heavyweight championships. The fight was aptly named ‘Moment Of Truth’.

It was a devastating knockout in a career laden with big nights and even bigger wins. Below we take a look at The Real Deal’s greatest ever nights inside the ring…

Vs ‘Buster’ Douglas, October 25, 1990, Las Vegas

Eight months prior to Holyfield’s assault on Douglas’ heavyweight titles, the champion had completed what is considered not only the biggest upset in boxing history but one of the biggest shocks in the history of sport altogether, when he flattened the seemingly invincible Mike Tyson in Tokyo.

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Unfortunately for Douglas he never did reach the heights of that momentous night in the Land of the Rising Sun again. He became lazy in the aftermath of his triumph over Tyson (parallels with Andy Ruiz Jr today, perhaps), living the life of a heavyweight champion without the work ethic, and turned up to The Mirage overweight (246lbs to Holyfield’s 208lbs) and uninterested. Holyfield dismantled Douglas and in the third round, after a wildly inaccurate uppercut threw the champion off balance, Holyfield replied with a straight right to his opponent’s chin, ending Douglas’ short-lived reign and ushering in a new dawn for the heavyweight division.

Vs Riddick Bowe II, 1993

Holyfield vs Bowe joins Ali vs Frazier, Ward vs Gatti and Barrera vs Morales among the creme de la creme of boxing trilogies. Holyfield fought many of the best fighters of an era across two divisions but, for whatever reason, Riddick Bowe always seemed to have his number when they met. The first fight between the two, which Bowe won via unanimous decision, is widely considered to be one of the greatest heavyweight bouts ever and the return leg, a little less than a year later, was expected to raise the bar even further.

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In the bout at Caesar’s Palace, dubbed ‘Repeat Or Revenge’, the action was just as relentless as the first with both fighters digging deep once again - this time it was Holyfield who was judged to have done enough on the scorecards, handing Bowe the only defeat of his career and allowing Holyfield to become just the third man to win back the heavyweight title from the man who beat him. 

Oh yeah, and a man with an ‘eff off fan strapped to his back (a la Moe Szyslak for The Simpsons fans) crash landed in the middle of the ring halfway through the fight. Forgot that part. 

Vs Dwight Muhammad Qawi, 1986

No fight proved to sum up the blossoming cruiserweight division and the curtain pull on the last of the 15-round fights better than the first meeting between a 23-year-old Evander Holyfield and Muhammad Dwight Qawi at The Omni in Atlanta, Georgia on 12 July 1986.

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Holyfield and Qawi were at entirely different spectrums of their respective careers when the two put pen to paper on their summer showdown, aptly named ‘Pandemonium’. Holyfield had only been a professional for less than two years, having won an Olympic bronze for the USA in Los Angeles in ‘84, picking up 12 wins from his first 12 fights. He was a hot prospect, but a clash with ‘The Camden Buzzsaw’ Qawi so soon in his career was considered a huge risk - Holyfield hadn’t even gone past eight rounds in his career at this point.

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When it came to fight night, Holyfield and Qawi revelled in one of the most punishing boxing matches of the 20th century (a whopping 2,308 punches were thrown) and although he eventually won via split decision, proving his doubters wrong and cementing himself as a future superstar, Holyfield had no time to savour his victory as the efforts of the battle left him in the hospital with kidney problems due to dehydration (he later claimed to have lost 15lbs during the fight).

Vs George Foreman, 1991

Since returning to the ring in 1987 after a 10-year exile, George Foreman had put together a 24-fight winning streak obliterating all but one exceptionally lucky soul within the distance. ‘Big’ George was back and more popular than ever. The interest in Foreman’s opportunity to regain the title, becoming the oldest heavyweight champion ever in the process, was huge, so a meeting with Holyfield was inevitable, not to mention lucrative, with Holyfield guaranteed an eye-watering $20m and Foreman a handsome $12.5m. 

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Foreman’s unprecedented assault on the heavyweight division 17 years after he lost the title in ‘The Rumble In The Jungle’ to Muhammad Ali was initially derided (there was a joke that the fight was between The Real Deal and The Big Meal because of Foreman’s weight) but he showed the world, even at 42, that he still meant business against Holyfield with the two descending into an all-out war that reached its peak in the seventh round - one of the craziest three minutes you’ll ever see in boxing.

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Though Foreman stayed competitive until the final bell, Holyfield won via unanimous decision and proved his quality against a grizzled veteran who’d go on to win the title again three years later, two full decades since he lost it, aged 45. 

Vs Mike Tyson, 1996

Nobody knew the Art of Intimidation better than Mike Tyson. The Baddest Man on the Planet was 45-1 when he and Holyfield met at the MGM Grand in Vegas, and very few who’d met him in the ring had survived long enough to hear the final bell. A 25/1 underdog with some bookies, many believed that Holyfield didn’t stand a chance in hell of beating Tyson, that he was over the hill and was even in danger of putting his health at serious risk. Holyfield though, unlike the score of poor souls who’d had the misfortune of facing Tyson before him, was not scared of the man from Brownsville.

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Using his superior strength, Holyfield could not be bullied and it left Tyson at a loss and unable to adjust as the fight progressed. It was all over in the 11th round, after a particularly punishing 10th for Tyson, when Holyfield battered his defenceless and well-beaten foe against the ropes, leaving the referee with no choice but to stop the contest. Holyfield became the first person since Ali to win the heavyweight title three times. 

In the aftermath Tyson told Holyfield, "Thank you very much. I have the greatest respect for you.” Seven months later he bit his ear off.

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