Boxing’s Five Greatest Moments: 1990-1999

By Matt McGrain on February 13, 2013
Boxing’s Five Greatest Moments: 1990-1999
At its best, boxing can reveal the soul; but on the rarest of nights, like in Tokyo, it infuses it.

Here are my picks of the five most heart-wrenching, stomach-churning, adrenaline-pumping, air-punching, on-the-edge-of-your-seat moments…

There was Julio Cesar Chavez and Meldrick Taylor. There were the Gatti wars against Robinson and Ruelas. There was Carbajal and Gonzalez and the fights that never were with the outstanding Ricardo Lopez. There were the great unsung champions, men like Antonio Esparragoza and Virgil Hill. Somehow there was still Roberto Duran, somehow still fighting for titles.

Suffice to say, this has been a harder task than the corresponding list for Boxing’s Five Greatest Moments: 2000-2009. In the end though, that just made it a more rewarding task. Coming back to the future has not been easy. Living in the 1990s for the past couple of weeks has been a bit of a blast. I want to share a little of that magic dust with you here. 

So climb into your grunge pants and dig out that Bat Out of Hell II CD: here are my picks of the five most heart-wrenching, stomach-churning, adrenaline-pumping, air-punching, on-the-edge-of-your-seat moments delivered to us by the greatest sport in the world between January 1, 1990 and December 31, 1999.

#5 “Maybe back to the days of Sugar Ray Robinson!”—Gil Clancy

Gil Clancy was and remains one of the great boxing men. Amongst others, he trained George Foreman, Oscar De La Hoya, Emile Griffith and Ralph Jones, a 1940s middleweight who held a win over a returning Sugar Ray Robinson.

When he put down the towel he picked up a microphone and became one of the best color analysts in boxing. Clancy was no company man and had manners born of his own mind. If he said something you could put faith in it.

In 1994, James Toney represented something of a throwback to the Clancy era. Absolutely elite he was ranked by many as the best fighter P4P on the planet and at 44-0-2 was unbeaten and the top dog at 168 lbs. There was a natural concern then when the inexperienced Roy Jones Jr. stepped up from 160 lbs. where yes, admittedly, he had looked literally other-worldly floating and flashing around the ring against his #1 contender, Thomas Tate, to take on “Lights Out” in his own backyard, a place where fighters like DeWitt and Barkley and Williams and McCallum had already been tossed. 

Jones looked pensive before bell where he normally looked sanguine. As a big Toney fan I expected James to drop a couple of rounds whilst feeling Jones out and then begin to take over. I knew Jones was good—so I paid him the respect of picking Toney on points, cleaning up the back straight after falling behind.

Jones did win the first two rounds. In the third, he knocked James Toney on his ass. As a punch it humiliated rather than hurt Toney but it was a blow he arguably never recovered from. 

For the next three rounds the fight seemed more a rattlesnake hypnotizing a cobra, as Toney set himself with menace but never quite struck out at the bucket of steel and piss that made no attempt to hide itself form plain sight but was never quite there, lashing out with sudden and deadly venom.

It was Clancy, commentating for HBO, who first understood what he was seeing in that ring. “Jones is never really directly in front of Toney!” he exclaimed in something very like wonder. It was true. Seven points ahead with six rounds remaining, Jones, in with the man who at the opening bell was regarded as perhaps the best on the planet, did not look particularly like he was going to be hit.

Asked about Roy’s combinations and if he had ever seen a middleweight that could throw such hurtful punches with such devastating speed, Clancy replied that he’d have to go back “a very long way,” paused and then said “Maybe to the days of Sugar Ray Robinson!”

Jones never did deliver on his astonishing potential. In many ways, this was his high-water mark. He utterly dominated James Toney in a way that was not thought possible and in a way he would never be dominated in again, but there was no shining moment for him in this fight, that flash knockdown hardly crystallizing perhaps the most astonishing performance ever seen in color. So for me it was always Gil who I think of when I think back to it, Gil who explained so perfectly what it was we were seeing: a modern-day fighter, a fighter of my generation who legitimately had the potential to be the greatest fighter of all time.

It never did happen but for those few seconds in that seventh round when Gil Clancy spoke, it seemed more than possible.

#4 “You don’t look big enough to wear three belts!”—Larry Merchant

Juan Nazario is crumpled face first on the canvas attended by his corner. Pernell Whitaker does a Native American war dance around his fallen opponent with both fists pumped in the air, whooping. He has just unified the world’s lightweight title after twelve years of fractured uncertainty.

Some background.

In 1987 a green Juan Nazario was matched with fellow Puerto Rican Edwin Rosario. Rosario had at one time been groomed for superstardom but after splitting a series with Jose Luis Ramirez (1-1), Hector Camacho shook some of the stardust from his countenance beating him by the narrowest of margins in June of 1986. Rosario was gearing up for his last shot at the big-time, with the planet-like Julio Cesar Chavez hovering into view. Nazario, once a sparring partner for Rosario, stood in the way.

If Rosario was driven, Nazario was a man possessed. All his life he had pushed his shoots out starved of sunshine, swallowed by the shadow his countryman cast. The attack he launched against Rosario at the first bell was a thing that appeals to the part of men that makes hunting, like fighting, a billion dollar industry. Most astonishing was the fact that when Nazario got inside he was all but dominating. Bulling his more esteemed foe before him he would wrestle and hassle his opponent, butting, elbowing and punching him to a standstill. Rosario was winning the fight with his boxing and that steaming right hand but the fight, for the first five rounds, was a barn on fire.

Coming closest to what would have been an astounding upset in the second round, he began to wilt after a brutalizing fifth but over and over again he would rally. In the seventh, after just such a rally but increasingly desperate he leaned into Rosario and bit him on the shoulder, in full view of the referee. The bite is the most pitiful of fouls. A seven-year-old child knows you don’t bite in a fight. I will not defend Nazario, then, but I will say that about this there was something of the slave and the master. Nazario sent a message with that bite, disgusting though it was: I am not going away. I will take what is mine.

Knocked out in the very next round, he made good on that psychotic promise in April of 1990. Rosario had lost to Chavez (TKO11) but picked up a strap eighteen months later from the excellent Anthony Jones. His first defense was a rematch with Nazario.

Green no more, Nazario fought a patient and mature fight, showing flashes of aggression up close but channeling that hostility. Rosario, in truth, was never in the fight. Stopped after the eighth having sustained a cut during a clash of the heads that was ruled accidental (OJ Simpson, too, was innocent) Nazario was in possession of an alphabet strap—ripped from the hands of his former oppressor, no less.

This, then, was the singular animal that Whitaker was matched with for his legacy. The build-up concerned itself with whether or not Nazario could reach Pernell with his unique mixture of brutality or if Whitaker was just too good for him. Most believed that latter. What nobody believed was that Whitaker would come out in the very first round, hold his ground, unleash a precision body attack that would bring his opponent’s guard down and then clip him through the jaw that had absorbed all those booming right hands from Rosario with a punch hard enough to leave him in thoughtful repost.

During this time in his career Whitaker was almost childlike in his delight. For most men the ring is a grave endeavor, one to be pursued with the utmost seriousness, and he did pursue it like that, up to a point, but he was so far ahead of his rivals—a even the great ones—that he could afford, sometimes, to adopt the posture of a kid playing basketball in his back garden. Whitaker treated boxing like it was just another sport. That’s how great he was.

“You don’t look big enough to wear three belts!” Larry Merchant chided a grinning Whitaker in the post-fight interview.

He was.

#3 “Wait a fucking minute now.”—Dad

As a rule, my father isn’t given to cursing and he was given to boxing only in that he was given to fighting. He didn’t know who anybody was, not really. The fighters he was interested in were the fighters of his own generation, Joe Frazier, Ken Buchanan, “real fighters,” you know how that goes.

But he knew Iron Mike Tyson.

His joining my friends and I to watch a fight was a treat for me and I was showing off a little, reassuring my pals that Mike would win, that this post-prison version was almost as savage as the one that had carved the division up in the late eighties, had he not proved that by stopping four men in a total of eight rounds over the last year? And this guy Holyfield, sure he’d been special once, but he was on the slide now, Bowe beat him and he’d looked horrible against Bobby Czyz last time out, he’d had heart trouble, he’d probably retire soon.

“Wait a fucking minute now,” interrupted my father. “That guy. Is gonna win.”

Evander Holyfield had begun his ringwalk. He looked like a man leaving the ring. He looked like he’d already won the fight. He looked like he was trying to decide whether or not he was going to kick his daughter’s boyfriend’s ass when he got her home after curfew. He looked like the arresting officer. He looked…smug. To a man, his entourage looked more nervous than he did.

I opened my mouth to disagree with the old man and then closed it. Opened it. Closed it again. I was reassured by Tyson’s suitably ludicrous entrance moments later but when he joined the huge underdog in the ring, the underdog smiled. He looked a like a pit-bull that has just seen a Chihuahua marking his favorite lamppost. He looked like a lion that has just realized his cage isn’t actually locked. It wasn’t that he looked confident, it was more than that. He looked utterly, utterly unconcerned—he looked indifferent. He wore a half sneer, as though this was somehow a waste of his time. 

Holyfield, like my father, believed in the messages in body language and he had read the signal Mike had broadcast in backing down when the two men had disagreed about territorial control of a pool table at the Olympic camp years before—the same theater for what he called their “slugfest” of a sparring session, called to a halt by staff due to its brutality. Since, his confidence in defeating Mike had been utter. When visiting schools between fights, Holyfield would explain the importance of standing up to bullies— then baffle staff by explaining how and why he would beat Mike Tyson, who he considered such. 

My hope was briefly restored when Mike wiped the smirk off Holyfield’s face with his very first punch, but Holyfield soon settled down to a job that was nothing less than exposing the limitations of the Tyson heart and mind, something he did thoroughly and completely.

In the 6th, Holyfield dropped Tyson with a savage left handed blow and whatever was left of the old Mike Tyson did not rise from the canvas. When he practically crawled back to his corner at the end of the 10th we were all on our feet and when he tottered out of it at the beginning of the next and the inevitable occurred at 0:37 of the 11th, it was hard to know who looked the more smug, Evander Holyfield or my old man.

#2 “I personally do hate him.”—Nigel Benn

Boxing as pantomime is not something that was really embraced in the UK prior to the ‘90s. We understood, post-Ali, just as everyone else did but Britain still liked her fighters grim-faced and valorous in defeat. Perhaps this was why, even though we recognized Chris Eubank for what he was, he came as something of a shock.

Preening, occasionally monocled, appealing during the hurly-burly of boxing press conferences for “parliamentary procedure” he became the man we loved to hate almost immediately. Eubank took to an extreme that thing you must never, ever do as a British boxer, he affected. He adopted airs and graces above his station. He had ambition, but not in the field of boxing, which he regarded as a “barbaric.” We wanted him beaten.

In the other corner was Nigel Benn. Eubank wasn’t qualified to fight Benn, but he flat-out talked himself into the fight, turning it from a possibility into a necessity with nothing but sheer bloody-minded pursuit.  The Dark Destroyer” had already been beaten, by the outstanding Michael Watson, but since then he had gone to the US and beaten up Iran Barkley (KO1), Doug DeWitt (TKO8) and Sanderline Williams (SD10). He was proven. Eubank was not. He was also a working-class hero and classically and understandably British—trouble as a juvenile; a stint in the army; and a straight-ahead kill-or-be-killed style as honest as the man himself.

But this was far from being a straight-ahead dynamic. Look closer and you will see contradictions. It was Benn, not Eubank that ate with a silver spoon. Whilst Benn was being groomed for superstardom by a heavy promotion team, Eubank was scrabbling in the grass for coppers. Whilst the army was turning Benn’s life around, Eubank was falling deeper and deeper into a life of crime and poverty. When he finally took up boxing across the Atlantic in the United States, he had to sweep up to pay his gym dues. 

It came to a head between the two at the signing of the fight contract, an event broadcasted live on ITV and hosted by a clearly uncomfortable Nick Owen.

Eubank refused to look at Benn in the studio. Benn seethed. “He was the first one to really give me a bit of stick,” he would say, years later. “So he lit the fuse.”

In the studio, he was more direct.

“I can’t wait for November the 18th…to give him a good, good hiding.”

In response, Eubank lit more than the fuse.

“He’s all hype. I came up the hard way. I didn’t have Frank Warren. I didn’t have [manager] Ambrose Mendy…”

Benn’s discomfort was plain. Eubank was achieving the astonishing duality of undermining his precious working-class credentials whilst simultaneously looking down upon him. Either one of these would have been unacceptable to a Glasgow greengrocer. To a professional fighter of Benn’s stature and background it was the emotional equivalent of tectonic plates shifting with the increased volcanic activity that entails.

Eubank had previously stated that he didn’t hate Benn, but that he had to beat him to “get out of the maisonette and into a house.” He maintained that position at the signing. “I don’t hate the man. I just want his title.”

Nick Owen tried to wrap the broadcast up on that note, but Benn interrupted him.

“I personally do hate him. I personally. Do. Hate him.”

When I heard those words the hairs on the back of my neck stood on end. This, then, was something different. Benn wasn’t playing any games. He wasn’t trying to build the gate. We were no longer watching pantomime. He hated Eubank as surely as he was going to try to knock him out. I suspect that he wanted to kill him.

Pre-fight is legend. Benn’s people colluding to ruin Eubank’s entrance; Benn himself shifting seven pounds of weight on the morning of the fight; the twenty million viewers tuned in to watch the promised mayhem—and a fight that somehow delivered.

One or the other was hurt in every single round. Eubank’s right hand was sudden and deadly. Benn’s body attack was as eye-watering as anything this side of Roberto Duran. 

There was sick poison in those punches.

It seems strange that there was a time when Eubank’s granite mandible was in doubt, but this was the night we found out that he probably couldn’t be stopped below cruiserweight, although Benn did drop him with a rocket-ship overhand swing in the 8th, Eubank feverishly protested a slip. His left eye almost completely shut, his gunslinger attack leaving him blown out, Benn missed his last best chance. Eubank brilliantly weathered the Benn storm and then started to come on. Lead right-hands softened him up throughout the 9th but when Eubank drove through him with a right hand and Benn was all at once gone it still came as something of a shock. These two had seemed something unbreakable. “I’m in too much pain to talk,” Eubank told television in the ring.

Seen with the right kind of eyes, this is nothing less than a triumph of the human spirit. Eubank’s desperation to better himself won out over Benn’s hatred. Seeing these two together these days, reminiscing, that hatred firmly behind them is an ending more perfect than the drawn rematch they fought in 1993.

Barry McGuigan called their first fight “our Hagler-Hearns.”

I think it was something even more than that.

#1 “My mother. Mother. Mother…God bless her heart.”—James Douglas

Mike Tyson and James “Buster” Douglas met in February of 1990 in Tokyo, Japan. For all that we recognized what it was we saw they might as well have met on Mars. The eerie quiet, to Western ears so strange to witness at a big fight, perhaps more normal for the Japanese fans who applauded respectfully after each round. We could hear everything—the punches going in the grunts and snorts of the fighters, the instructions of their respective corners (“Get in baby!  Get in there baby!)—the soft bounce of leather on canvas. “You could hear a rat pissing on cotton,” is how Tyson’s chief second Aaron Snowell summed it up. For perhaps the most infamous fight in history we were treated to the most intimate of broadcasts. It infused the fight with a dream-like quality. Was it all real?

Buster won the first round. This sometimes happened when we were waiting for Mike to knock out his overmatched opponents. Douglas certainly fit that bill; he was basically regarded as a deluxe journeyman in the build-up. Here was a guy who could beat Oliver McCall but not a green Jesse Ferguson. As Buster’s own uncle put it, Douglas won every fight Don King wanted him to and lost every fight Don King wanted him to. There was no fight Don King wanted him to lose more and there was never a fight he was so thoroughly expected to lose.

Through the third round Buster threw 114 jabs. Half of these punches had landed.  Douglas had a beautiful jab, all 83 inches of it, a real thumper. He had put the tough Mike Williams down with it more than once in their fight two years previously and tended to win any fight he got this punch working in—and it was working for him in Tokyo. But he wasn’t just outboxing Tyson.He was outfighting and outthinking him, he was faster to the punch and he was finding the right punch with unerring consistency. In the weird silence of that early morning he was putting a beating on a man that had made him a 42-1 outsider.

By the 8th the fight seemed almost out of Tyson and when he glared balefully at the unexpected thorn in his paw it was through one eye. But Iron Mike was and is regarded as a great heavyweight champion. If it is true then he showed his greatness here for just as we began to write him off, he came through, through the smallest of openings left behind what was a rather tired jab from Douglas behind which he for once failed to move, an opening just big enough for a detonated uppercut. Enough has been written about the validity of that count that followed to fill a book, but the only thing I would ever say is that it has nothing to do with Douglas. To paraphrase Gene Tunney, the beneficiary of the only count comparable in fame to this one, the ten seconds on the floor belong to the fallen fighter and those ten seconds are tolled off by the referee. If a fighter is up at nine, he survives and Douglas did survive and he went back to his corner and he sat down and he told them there:

“I got him.”

“What?”

“I got him.”

Two rounds later, he got him. Tyson began the 10th with a hard right hand but then allowed himself to be handled and walked, first to his own corner, then around the ring whilst Douglas recovered. When punching resumed, Douglas was in the box seat once again, five sharp jabs against a disorganized Tyson who seemed almost indifferent as Buster uncorked his own torpedo-like uppercut and then beat Mike straight onto his back. It is literally the most incredible, unreal moment in the history of the sport, of sport full stop. The sense of unreality continues to deepen as Tyson blindly gropes for his gumshield and sticks it into his mouth back to front as the referee tolls through 6, 7 and 8, as though he wouldn’t be allowed to continue were it left languishing on the canvas where he instead was languishing and then he had been counted out. Just like that.

There are technical issues. Douglas was brilliant in shielding himself from Mike when the two bumped up together and unsheathing a hidden uppercut, thrown across himself from safe position; his jab, always formidable, was never better; the straight right was a punch he never failed to sit down on and refused to be kowtowed into sheathing when Tyson fired back. But the search for answers was remained. How? When Larry Merchant cornered Douglas in the ring (something Tyson was not able to do in ten hard rounds) it was his second question.

“Why did it happen, James?”

Speaking years later, Douglas said what we all had been thinking when Tyson finally got to him and decked him. “I could easily have gone out there,” he said, “and given a lackluster performance, or probably try once or twice and say, Aw, the hell with it.”

This makes sense. Douglas had done exactly this whole career. What was different this time?

Three weeks before the Tyson fight, his mother Lula Pearl had passed away. Douglas was immediately asked if he wanted to postpone, and he replied no, that his mother would not have wanted this.

“Say, Aw, the hell with it…but that was the last thing I would allow to happen. Because my mother was such a very strong woman and I couldn’t go out like that.”

When Tyson dropped him and the count was at five, Douglas motioned to get up, then stopped like he had quit. Then he changed his mind and stood, almost as though prompted.

“It was a really difficult time in my life. Boxing helped me make it through it, it took my mind off it, you know, my personal problems. So therefore [Tyson] was the least of my worries.”

Douglas began to grieve in the ring that night, something he had not been able to do in the normal way three weeks before the biggest night, the only chance, of his professional career. Larry Merchant’s question was the beginning of that process. At its best, boxing can reveal the soul; but on the rarest of nights it infuses it.

“Why did it happen, James?”

“My mother. Mother. Mother. God bless her heart.”

Boxing’s Five Greatest Moments: 2000-2009   
Boxing’s Five Greatest Moments: 1990-1999   
Boxing’s Five Greatest Moments: 1980-1989     
Boxing’s Five Greatest Moments: 1970-1979

Follow us on Twitter@boxing_com to continue the discussion

1994-11-18 Roy Jones Jr vs James Toney



Pernell Whitaker vs Juan Nazario.avi



Tyson vs Holyfield 1 FULL FIGHT



I Personally Do Hate Him



nigel benn vs chris eubank 1 full show



Mike Tyson VS James Buster Douglas 1990-02-11



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  1. the thresher 11:14am, 02/24/2013

    Everybody remembers where they were when they heard that Buster had waxed Tyson.

  2. pugknows 06:21pm, 02/15/2013

    The Thresher has the beat.

  3. the thresher 05:40pm, 02/15/2013

    The ones that are hard to do are often the best.

    I liked it so much I read it again.

  4. Matt McGrain 11:20pm, 02/14/2013

    Thanks gents, I appreciate that.  It was hard work this one for some reason.

  5. Jason 02:25pm, 02/14/2013

    I’ve always held Douglas’ victory over Tyson as one of the very best performances I’ve ever seen. I’m not saying I’ve seen them all, I’m only saying from what I have seen, Douglas’ performance, considering the circumstances, the era of his day, who he was fighting, is close to being unequaled.

    I always thought this was the closest comparison in order to settle the classic question: Who would win between Tyson and Ali.

  6. Jason 02:18pm, 02/14/2013

    Awesome picks! Thanks for sharing.

  7. raxman 01:10pm, 02/14/2013

    this was just a fucking great read Matt. i loved every sentence. well written and totally entertaining. i somehow missed the 2000-2009 version so i’m on that now!!!

  8. peter 01:03pm, 02/14/2013

    Excellent article. Unique. I like the personal touch. Thanks.

  9. bikermike 08:35am, 02/14/2013

    Mr McGrain,  Thank you for a great read.

  10. the thresher 07:17am, 02/14/2013

    What a fantastic piece. Another that makes me proud to be on here and another that reflects a lot of hard work and research. Unlike most other sites that feature superficial and short works, these are true essays that have soul and a story to tell.

    The part about Buster is priceless.

    Thanks Matt for great read.

  11. Rick 06:56am, 02/14/2013

    Nice piece. I enjoyed that.

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