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Tyson/Bowe/Lewis/Holyfield: Timing is Everything

By Gabriel Montoya

“Greatness is mostly timing, which is mostly luck”


-Scott Adams"

Boxing is the best and the worst of the free enterprise system. You get what the public will bear." -Rock Newman



 It started with an email for my Monday Mailbag back in June.


What’s up gabe?


Hope u enjoyed your weekend though you’re not saying what you did (dude it’s cool, if u had a Murder she wrote marathon we wont judge).

I’m fairly new to the sport and got a quick question and would like a fairly in depth answer. What happened that Lewis – Tyson – Bowe never all got it on in their primes. I’ve asked around and gotten a bunch of contradictory answers. I’m sure I could have Googled it but then I wouldn’t be in the mailbag.


Thanks, Ed from N.Y.C



I’m no historian. Over the past few years, as my work as a writer has taken me deeper and deeper into the world of boxing, I’ve brushed up as much as I can and have worked hard to know the history of the sport I have watched one-dimensionally from my TV since I was a child. When you are a kid, you don’t even think about the business dealings, the odd rankings, why fights didn’t happen or did, unless maybe you’re Steve Kim or Thomas Hauser. I was one of those guys who bought hook, line, and sinker that the sanctioning bodies are evil and Don King ruined boxing without knowing any details. Yeah, I can say it. Early on, I was one of the uneducated “sheeple” when it came to the business of boxing. These days, I would say I’m one of the semi-educated people.


This question languished in my inbox for some time. Why didn’t they fight in their primes or at all? Right away, I knew I was going to have to dig and ask around about old history. And when it comes to history, the victors generally get to tell the “real” version. Only in the case of Lennox Lewis vs. Riddick Bowe, there isn’t a victor beyond the amateurs. And I wasn’t able to get a hold of Lewis or his people so, in the interest of full disclosure, I did the best I could putting together the pieces of why Lewis-Bowe never happened. Why Bowe-Tyson never happened is a much clearer picture.  


So here you go, Ed from NYC, my first feature based on a Monday Mailbag question. Thanks for pushing my limits and expanding the horizons of a writer who was never really into the heavyweights. I hope this clears up your question.

In order for a great fight to happen, a combination of factors need to align; willing participants, the right stakes at the right time, a perfect complement of styles, and a public need to see it. When I think of why Lewis-Bowe-Tyson never fought, the key missing ingredient is timing.


We begin in August of 1987. Brownsville, NY (by way of Catskills, NY) phenom “Iron” Mike Tyson, a seemingly perfect fighting machine  becomes not only the unified heavyweight champ by beating Tony Tucker via 12-round decision, he becomes the first heavyweight champion to hold all three major belts, WBC, IBF, and WBA, at the same time. Added to which he is the youngest heavyweight champ ever and “the baddest man on the planet” at that particular time. Tyson finishes off the year by beating 1984 gold medal winner Tyrell Biggs’ ass in seven rounds and releasing “Mike Tyson’s Punch Out” for Nintendo. Not a bad year, if you ask me. All looks sunny as hell for the champ at this point.


In the 1988 Olympic Games in Seoul, Korea, English-born but Canadian resident (by way of Jamaica at some point) Lennox Lewis stops Brownsville, NY native and legendary trainer Eddie Futch’s prodigy Riddick Bowe in two rounds to take Olympic superheavyweight gold. Bowe gets the silver. Lewis is a 6’5” 225+ pound right hander who possesses not much else but a pawing and sometimes punishing jab and a hammer of a right hand. He fights upright, is stiff, and has not found the gift of rhythm that Hall of Fame trainer Emanuel Steward will give him later in the ‘90s.


Bowe is gift from the boxing gods; a right-hander with a high boxing I.Q., an easy, relaxed way about him, and all the punches to go with excellent long, mid, and inside games.


Of the two, Lewis is raw in terms of skills but a strong-willed winner. Bowe, a natural-born fighter with all the tools but is a little fragile in the focus department.


It’s a match made in pro boxing heaven.


Meanwhile in the pros in 1988, Tyson demolishes the last vestiges of Larry Holmes with a four-round beating, beats a tubby Tony Tubbs senseless in four, and puts Michael Spinks on his back and wondering in 91 seconds to claim the linear title to go with his alpha-belts. Tyson is now the clear and undisputed heavyweight champ of the world.


At the same time, Evander Holyfield unified the cruiserweight titles (also a first) and began his ascent to the heavyweight ranks. In my family, this was the guy my brother, Danny, convinced us all would beat Tyson. Not germane to the story but I want to make sure Danny gets his props for calling it. In the world of boxing, “Commander Vander” loomed as a clear threat to Tyson in a box office gold matchup.


In March and June of 1989, Bowe and Lewis turn pro, respectively, and are both set on aggressive schedules. Bowe would end the year at 12-0 with 10 KOs to Lewis’ 6-0 with 5 KOs.


Tyson, meanwhile, is at the height of his powers and TKOs British heavyweight Frank Bruno in five rounds and American Carl “The Truth” Williams in one. The table is set for a Tyson-Holyfield showdown in mid-1990. All Tyson has to do is beat Buster Douglas and the matchup the boxing world is now clamoring for will be set in motion.


February 11, 1990, a night I will never forget as long as I am alive. Tyson gets knocked out by James “Buster” Douglas in Tokyo, Japan in one of sport’s biggest upsets ever. For one night only, Buster Douglas, a 42-1 underdog and classic underachiever, put it all together to be king of the world for a night.


Douglas ends up doing a world tour, losing focus but gaining tons of weight. Holyfield knocks his block off in October of 1990 with a third-round stoppage that was among the biggest anticlimaxes of a career in boxing history.


By the end of 1990, Tyson had rebounded with wins over Henry Tillman and Alex Stewart while Lewis and Bowe rounded out their years at 14-0 and 21-0.


Bowe, the last Futch protégé is looking like the next great American heavyweight.


Lewis, despite the amateur win over Bowe and the gold medal, still feels like an awkward work in progress.


1991 saw two fights from Tyson against Jamaican-born raw contender but savage puncher Donovan “Razor” Ruddock. Though “Iron” Mike had lost his “0,” he was still an incredibly popular fighter. These two fights showed Mike proving his mettle and having to earn it a little bit. Tyson took the wins stopping Ruddock in a controversial TKO in seven in March and by decision over 12 rounds in June.


The stage is now set for Tyson-Holyfield at Caesars Palace on November 8, 1991.


In 1991, Bowe wins seven fights against six men, Tyrell Biggs via eight-round stoppage, Bruce Seldon in one, Tony Tubbs via decision in ten and Elijah Tillery twice, the first of which was one of the odder fights of all time.


Bowe was beating Tillery fairly easily in the first and even dropped him. But after the round, Tillery started talking trash and stepped to Bowe who socked him in the face. Tillery kicked at Bowe and all hell broke loose. Bowe’s manager Rock Newman got all WWE, hopped on the ring apron and grabbed Tillery from behind along ropes as Bowe wailed away. It was pure mayhem as Tillery fell/was pulled out of the ring. He was summarily DQ’ed for starting the thing by talking trash (Yeah, I don’t get it either) and a rematch was set. Bowe ended that one in four rounds. Rodolfo Marin and Philip Brown rounded out the fallen group of foes.


Lewis fought just four times, ending his year with a three-round stoppage of 1984 Olympic gold medal winner Tyrell Biggs. It’s clear that Bowe is moving into position to contend while Lewis is a few steps behind in development but gaining steam.  


Now before Tyson-Holyfield can happen in November at Caesar’s Palace, Tyson hurts his rib cartilage in training camp and the fight is postponed. Then in July of 1991, Tyson is arrested for the rape of Desiree Washington, an 18-year-old beauty queen. He is convicted and is incarcerated in Indiana Youth Center until March of 1995.


More bad timing; Tyson moves back into title contention and a possible round-robin with Bowe and Holyfield with Lewis looming as well but instead goes to jail for a booty call gone horribly wrong.


Holyfield ended up taking on Bert Cooper instead of Tyson that November and then started off 1992 by fighting Larry Holmes.


Now the stage was set for Bowe-Holyfield which happened on November 13, 1992. Bowe took the title in the first of a classic trilogy. It was seesaw affair that featured some of the greatest rounds of heavyweight action, none greater than the tenth round that saw both men hurt and come back to punish the other for the infraction.


Now you have to think about how rare this is. Not only were great fighters taking on each other for all the marbles, three belts at a time had passed from Tyson to Buster Douglas to Holyfield to Bowe and had remained with that champ.


But this would not last long.


According to Kelly Swanson, who was Bowe’s publicist during his career, a two-fight deal was offered to Lennox Lewis, who was now in position as the number one mandatory challenger for the WBC belt. The deal was that Bowe and Lewis would fight on the same card to build the fight in the U.S. Lewis had spent a lot of his career by that point in England and was a relatively unknown fighter here in the states. In the second fight of the deal, the two would fight with “Lewis being guaranteed $9 million rather than 1/3 of the gross revenue,” according to Swanson. Now it’s important to note that as a mandatory challenger, Lewis was entitled to 1/3 of the gross. He was not avoiding the fight but rather avoiding making less than what he was entitled to.


Now consider this, under the guidance of mercurial manager Rock Newman, who was unique in that he was an independent manager who only handled this one client and maneuvered him brilliantly and controversially to the title, Bowe went from getting an offer of $400,000 by HBO to fight Pierre Coetzer one fight before the first with Holyfield (Newman settled for $650,000) to signing a six-fight $100 million dollar deal with HBO after beating Holyfield. So when Lewis turned down that offer, which eclipsed the mere $200,000 he had made so far for a fight, he was looking at what the other guy was making and what he was entitled to by sanctioning body rules.


Bowe held an infamous press conference and dumped the WBC belt in the trash. Bowe and Newman were not men to be dictated to by sanctioning bodies they felt were under the thumb of promoters Don King and Bob Arum. Subsequently, the WBC made Lewis their champion. He “won” the belt in street clothes rather than how he had hoped.


In 1993, Bowe began the year by defending his two remaining belts in early KO wins over Michael Dokes and Jesse Ferguson.


A rematch with Holyfield took place November 6, 1993. This time, Holyfield brought Manny Steward to his corner and fought a much different type of fight, darting in and out of range and boxing Bowe rather than going toe-to-toe as in their previous war. Bowe had been on a year-long world tour, eating everything in sight and not keeping his focus despite his easy wins. He was not the man who was hungry for success the year before. Still, the fight was competitive and featured the all-time weirdest thing to happen in a ring. Not even Tyson biting Holyfield’s ear off years later or Kermit Cintron getting diving gold could top it.


A man propelled by a fan on his back, the “Fan Man,” flew into the open air Caesar’s Palace arena and got tangled in the lights in the seventh round. All hell broke loose. Bowe’s pregnant wife fainted and was taken to the hospital, “Fan Man” was beaten senseless by members of Bowe’s entourage, and the fight was delayed for 20 minutes or so. Finally it resumed and Holyfield took the title back via majority decision. For the win, he was named ABC’s “Wide World of Sports Athlete of the Year.” Yeah, this was when fights mattered to the world at large.


This takes us to time number two when Lewis and Bowe almost fought.


After Bowe lost the title, a fight contract was signed in 1994 for Bowe to fight Lewis for the WBC title Bowe had discarded in the trash. But a funny thing happened before that fight could take place: Then 24-5 journeyman Oliver McCall TKO’ed Lewis in two rounds off a beautiful left hook/right hand combo. The contract, like Lewis’ paper title reign, was null and void.


Now, let’s jump back a few months to March, the month Mike Tyson is released from jail and into the arms of Don King where he will set forth to begin a campaign to get his belts back.


Now it’s interesting to note how the stage was set and what we might have missed out on with Tyson had this proposal gone through. This is from the article “Up from the Canvas” by Richard Hoffer for Sports Illustrated, March 27, 1995:


“Would you grind your teeth a bit if you knew that early last year a plan was proposed that would have unified the heavyweight titles then held by Holyfield (WBA and IBF) and Lewis (WBC)—with a provision for the IBF’s top-ranked Moorer to fight the winner—but was scuttled because IBF president Bob Lee was suddenly worried about his organization’s No. 2 contender missing out on the action? That fighter, Oliver McCall, eventually fought Lewis for the title, won it and gave King, his promoter and the prince of persistence, entree back into the heavyweight championship money.

"It was our one opportunity to unify the heavyweight championship," says promoter Dan Duva. "Now we don’t have a world champion. It’s terrible." Politics, says Duva, "is the problem in boxing. It shows that the organizations don’t care about what’s best for boxing."

And the failure to rank Bowe has gone past the point of irritation. Bowe certainly made a major gaffe when he literally dumped his WBC belt into a garbage can. For that sin, coupled with the larger sin of not taking care of himself and losing his rematch with Holyfield, he has become a nonboxer. Unbelievably, he is in none of the major sanctioning bodies’ top 10. King proposes an elegant metaphor to explain this: "Herein lies an immigrant who is capable of treasonous activity. So he was deported."

Tyson gets out in March 1995. The belts are splintered. Southpaw Michael Moorer has beaten Holyfield for the WBA and IBF belts to become the first southpaw to hold the titles but loses them to a 45-year-old “Big” George Foreman in his next fight.


This is where boxing plays musical belts.


McCall has gone on to beat an even older Larry Holmes and then loses his belt in late 1995 to Frank Bruno.


Foreman gets stripped of the WBA belt for not fighting freakin’ Tony Tucker and then loses his IBF belt after he beats Axel Schulz but won’t rematch him.


Bruce Seldon beats Tony Tucker in April of ’95 via seventh round technical decision for the vacant WBA strap taken from “Big” George.  


The world wants their newly-freed champion Mike Tyson to take his throne. Every fighter with belts, names and/or drawing power wants the huge payday a fight with iron Mike can give him.


Meanwhile, Riddick Bowe, still a dangerous heavyweight, is beltless and unranked by all three major sanctioning bodies; a victim of his own independence and lack of discipline. Thusly, he is not in Don King’s or Mike Tyson’s immediate plans. He continues winning, though with a decision over Herbie Hide in December of ’94.


In ’95, Bowe takes out Larry Donald and Jorge Luis Gonzalez and sets the stage for a third Holyfield fight. In a surprise, Holyfield, who had complained of heart issues in the Moorer loss, was stopped by Bowe. Despite dropping Bowe earlier in the fight, Holyfield faded quickly and it was over in eight. There were now whispers that Holyfield is all done in. Yeah I know. In 1995. Go figure.


At the same time, Lewis is still picking up pieces of his chin off the mat and rebuilding with wins over Justin Fortune and Lionel Butler. His next win was over Tommy “The Duke” Morrison, an Oklahoma power-puncher with a left hook from hell and a mullet that drove the girls wild.


Mike Tyson would tear through the division, gobbling up Peter McNeeley in August 1995 on pay-per-view to the tune of $96 million worldwide and 1.52 million PPVs in the U.S. In December, he eats Buster Mathis Jr.’s lunch in three.


In March of 1996, Tyson takes Frank Bruno’s WBC belt and then takes Bruce Seldon’s WBA belt in September via a phantom punch that grazes the top of Seldon’s head and puts him down for the count. My brother, Thom, has a VHS of that tape labeled “Fixed Fight.” Just sayin.’


Lewis would fight just once in 1996, a WBC title eliminator against “Merciless” Ray Mercer, the 1988 heavyweight Olympic gold medal winner for the U.S. It was a savage affair that featured great back and forth action throughout. I thought Mercer won but check it out and get back to me. Lewis would set to take on Oliver McCall the following year in yet another bizarre fight.


For Riddick Bowe, 1996 was a Waterloo of sorts. He had just two fights but in those, two lay the seeds of his destruction. He faced one Andrew Golota at Madison Square Garden on July 7, 1996. Golota, a Polish national heavyweight with power in both hands, an upright style, and penchant for dirty fighting took Bowe to task, beating him from pillar to post. Bowe, once again showed his lack of discipline and had come into the bout 252 pounds, a career high. But Golota was a bit screwy and despite being ahead in the fight, could not help himself and was disqualified when he repeatedly low-blowed Bowe until the former champ fell to the canvas, unable to get up. A riot ensued. Golota was beaten by a Bowe entourage member and took 11 stitches in the head; fans and police were injured. Safe to say, it joined the “Fan Man” fight in the pantheon of weird boxing moments.


The rematch in December was no different. Golota dropped Bowe who in turn dropped him. But again, “The Foul Pole,” as he would later be nicknamed, Golota was leading on all cards in the ninth when he was disqualified for again punching Bowe low, time and again. No riot this time but a nickname was born and the beatings that Bowe took effectively ended his time as a top contender. Blowing up in weight and the wars with Holyfield took their toll on Bowe and he began to slur his words a bit. Soon after the Golota rematch, Bowe retired, going into bizarre stunts like joining the Marine Corps briefly and run-ins with the law. Though he would make an ill-fated comeback in 2004, any hope of moving into position to fight a Tyson, Lewis or Holyfield died in the Golota fights.


Tyson’s 1996, as good as it started with the belt collecting from Seldon and Bruno, would not end on a good note. Holyfield, thought to be past it after a lackluster win over Bobby Czyz in May, was finally set to fight Mike Tyson.


The fight, called “Finally,” came off without hitch on November 9, 1996 at the MGM Grand and it was the war we all expected. Tyson tried early to hurt Holyfield, who was not given a chance in hell to win the fight. Holyfield fought masterfully, manhandling Tyson and tying him up while pushing off and dropping in chopping rights and left hooks. By the middle of the fight, it was clear the time out of the ring and the quick fights to get to this point had not prepared Tyson for the kind of warfare Holyfield was letting loose on him. In one of the great upsets, Holyfield stopped Tyson in 11 rounds to become the second fighter since Muhammad Ali to hold the belts three times.


In 1996, Tyson won the WBC belt along with the WBA belt. The first Holyfield fight was only for the WBA belt. That belt, which was stripped, would eventually find its way back onto Lennox Lewis’ waist in February ’97 against Oliver McCall in yet another freaky incident. McCall began to cry in the fourth round and began to turn his back on Lewis. He did it again in the fifth and seemingly did not want to fight but only cry. It was a full-on mental meltdown and Lewis was given the win and the belt.


Holyfield and Tyson would rematch in the MGM on June 28, 1996. It was- you guessed it- yet another bizarre chapter in boxing history. The fight was hotly contested early. Mike, who had complained of the headbutts from Holyfield in the first fight, took umbrage at a headbutt from Holyfield that opened a huge gash over his right eye. In retaliation, he bit off the crown of Holyfield’s ear and then when the fight surprisingly resumed, he nibbled at the other ear. He was disqualified in three rounds and his license was revoked.


“Iron Mike’s” career would dismally spiral downward from there. He would eventually fight Lewis in 2002 but it was a meaningless, almost ceremonially, one-sided beating that Tyson admitted afterward he took only because he needed money.


Holyfield and Lewis would go on to share two hotly contested fights in March and November of ’99. In one of the worst decisions in the annals of boxing lore, the first fight was declared a draw even though Lewis had very clearly beaten Holyfield, who was showing signs of fading as a fighter. The rematch in November felt more like a Holyfield win but was awarded to Lewis. It was the boxing equivalent of giving Paul Newman an Oscar for “The Color of Money” but not “The Verdict.”


So there you go, Ed. I hope that answers your question. There may be more to it than that but that’s as clear an answer as I think I can give you. Hope this helps and I’ll see you in next week’s mailbag.


Have a great weekend, fight fans.


You can email Gabriel at, follow him on Twitter at catch him on each Monday’s episode of “The Next Round” with Steve Kim or tune into hear him live on Thursdays at 5-8 PM PST when he co-hosts the BlogTalk radio show Gabriel is a full member of the Boxing Writers Association of America.

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