Remembering Holyfield vs Bowe: The Greatest Heavyweight Trilogy Ever

The Bowe-Holyfield battles of the 90s stand alone as the greatest series in heavyweight history.
14:17, 06 Mar 2024

On this day in 1989, Riddick 'Big Daddy' Bowe made his boxing debut. The iconic heavyweight kicked off his campaign with a second-round knockout of Lionel Butler in Reno, Nevada. Bowe would go on to compete in the greatest heavyweight trilogy of all-time. With all due respect to the triple-helping of superb violence that Tyson Fury and Deontay Wilder have served up over the last few years, Evander Holyfield and Riddick Bowe staged the finest three-fight series in heavyweight history. The two great champions shared three fights of furious action, intense fascination and a stray Fan Man.

Before a glove had been laced, the first meeting of these two warriors had all the makings of a classic. The undisputed champion Evander Holyfield was meeting an unbeaten puncher who was widely agreed-upon as the legitimate number one contender. ‘Big Daddy’ had built an unblemished 31-0 record in very good company. Former heavyweight champions Tony Tubbs and Pinklon Thomas, as well as future belt-holder Bruce Seldon, had fallen. World title challenger Bert Cooper, who himself had just floored Holyfield for the first time in his career, had also been wiped out by Bowe in two rounds. The champion entered as the betting favourite, but Bowe was as worthy as challengers get.

The action on the night did not just live up to this finely-poised match-up, but far surpassed anything spectators were expecting. A savage, evenly-contested war of attrition saw Holyfield outworked and outpunched by his bigger foe. The tenth stanza, which would win The Ring magazine’s Round Of The Year, saw ‘The Real Deal’ retake territory from ‘Big Daddy’. After eating several Bowe combinations, Holyfield roared back, showing why he would go down in history as one of boxing’s finest warriors. However, the champion had punched himself to a near-standstill in the draining round.

The eleventh saw Bowe come out stronger, wailing away on the flagging Holyfield. Knocked down by a brutal right, commentator Jim Lamptey claimed it was a “miracle” the champion made it to the end of the session. Inconceivably, the twelfth round saw the deeply religious Holyfield mount a Lazarus-like resurrection. Bowe ended the fight on the back foot as Holyfield tried desperately to get the knockout he knew he needed to win. It was to no avail, Bowe stayed standing and won the championship by unanimous decision.


The two men would briefly embark on separate paths before reconvening for a rematch. The deposed champion parted ways with longtime trainers Lou Duva and George Benton, joining up instead with Emmanuel Steward. He would fight once before meeting Bowe again, a dominant unanimous decision over Alex Stewart. 

Bowe would be more prominent, and controversial, in his dealings between fights. ‘Big Daddy’ infamously threw his WBC title belt in the trash, rather than fight mandatory challenger Lennox Lewis. The reasons for the stunt have been debated, with the champion maintaining the purse split for the proposed fight was unacceptable, while others reckon Bowe didn’t fancy his chances against Lewis. He defended his remaining portions of the crown twice, knocking out Michael Dokes and Jesse Ferguson in less than three rounds combined. Bowe drew some derision for his choice of opponents, but nobody would criticise him when he finally agreed to a second meeting with Holyfield.

The second scrap would prove to be even more memorable than the first, but not totally for boxing reasons. That’s not to say the action wasn’t scintillating. An incredibly close battle played out, with Holyfield improving on his last performance to give Bowe all he could handle. The champion started strongly, winning the first three rounds, before ‘The Real Deal’ came storming back to clinch rounds four, five and six. But it was an incident that occurred during the seventh round that would see this fight transcend boxing altogether, and find a bizarre place in popular culture folklore.

SM News Evander Holyfieldjpg1

As the fighters resumed hostilities, suddenly a man paraglided into the arena and collided with the overhead lighting. His parachute got caught in the rigging, and he fell onto the top rope before toppling into the crowd, who wasted no time beating him. James Miller, more commonly known as ‘The Fan Man’, would go on to make more controversial interventions at major sporting events, including an FA Cup tie between Bolton Wanderers and Arsenal. The events of this fight were such a sensation that The Simpsons would parody them in the legendary episode ‘The Homer They Fall’.

Once Miller’s bruised body and ridiculous contraption were cleared from the area, the fighting resumed. Holyfield got the better of it, conserving his energy for eye-catching bursts at the end of rounds that captivated the watching judges. After the men went to war in a furious twelfth, the judges awarded Evander the win by majority decision, making him just the third heavyweight in history to regain the title from the man who defeated him for it.

The two men would once again go their separate ways, spending a two-year period fighting other opponents. Bowe won three fights with one no-contest, beating Herbie Hide for the WBO championship along the way. Holyfield endured a rockier road to the third fight, losing his newly-won belts to Michael Moorer in his next outing. He briefly retired after the fight, citing a heart complaint that he would later clarify had been misdiagnosed. Upon his return, he scored a solid points win over Ray Mercer.

The trilogy fight would be the only contest between the pair without a world title on the line. While Bowe was the reigning WBO champion going in, that particular belt did not enjoy the recognition it does today, and Holyfield chose not to compete for it in fear of hurting his ranking with the more established WBA, IBF and WBC groups.

The lack of championships at stake did little to dull the action, as Bowe and Holyfield picked up where their remarkable first two fights left off. Perhaps the most violent and taxing of their bouts, both men were knocked down over the course of eight savage rounds. Ultimately, ‘Big Daddy’ would prove too much for the brave warrior. Holyfield was still swinging when he went down for the final time in the eighth round, and even answered the count of referee Joe Cortez. But the fight, and the trilogy, was over.

Riddick Bowe had a 2-1 advantage in the greatest heavyweight trilogy there ever was, but he did not end up having the best career of the pair. His next two fights were a pair of disqualification wins over Andrew Golota, who had out-fought Bowe in each bout before his frequent fouls got the best of him. Bowe wouldn’t fight for the next eight years, before returning for three low-key victories in the mid-2000s.

Holyfield would go down as one of the greatest heavyweights of all-time. Two fights after the third Bowe battle, he upset Mike Tyson to win a fourth heavyweight championship. Years later, he would add a record-breaking fifth, beating John Ruiz to clinch the WBA belt. Holyfield retired in 2011, before coming back for a farcical exhibition fight with Vitor Belfort this year.

But it is far better to remember the two warriors for what they were than what they are. In the mid-1990s, Riddick Bowe and Evander Holyfield gave us the greatest trilogy in the history of heavyweight boxing. We may never see three fights quite like these ever again.

Suggested Searches:
The Sportsman
Manchester United
Manchester City
Premier League
Sportsman HQ
72-76 Cross St
Manchester M2 4JG
We will not ask you to provide any personal information when using The Sportsman website. You may see advertisement banners on the site, and if you choose to visit those websites, you will accept the terms and conditions and privacy policy applicable to those websites. The link below directs you to our Group Privacy Policy, and our Data Protection Officer can be contacted by email at: [email protected]

All original material is Copyright © 2019 by The Sportsman Communications Ltd.
Other material is copyright their respective owners.