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Fights That Could’ve, Should’ve But Didn’t Happen

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Fights That Could’ve, Should’ve But Didn’t Happen

It's finally happening. Long-time British rivals Amir Khan (34-5, 21 KO's) and Kell Brook (39-3, 27 KO's) will meet in a 149-pound catchweight bout on February 19th. This fight always seemed inevitable, but for many reasons, they had a difficult time finalizing a deal to meet in the ring during the last decade. Politics had something to do with it. Personal feelings towards the other may have played a part. Money may have been an issue as one or the other (or both) may have had an inflated value of what they brought to the table compared to what may have been offered. For whatever reason, when both were in their prime and when the fight would have been massive, it just didn't happen.

This is a fight that should have happened more than five years ago. Photo Credit: Sky Sports

Maybe the best explanation for why it is happening now and not say five years ago is that everyone involved, including the fighters, knew that they could meet anytime, and the fight would still be big. Why fight in their prime when they could wait until the end of the road for one last big payday? This is perhaps the best reason in explaining what took so long to put this fight together.

Many other potential matchups in boxing once seemed inevitable but never came together for one reason or another. Here is a look at some such fights that we as fans thought for sure we'd see one day but just never happened in the past 30 or so years.

Lennox Lewis vs. Riddick Bowe

If there were a boxing poster for fights that should have been made but weren't well, this would be the number one seller. The casual sports fans, the ones who say only watch the biggest of the big fights, knew of and wanted this fight. But it never happened. At least in the pros. And the reason can only be pinned on one side.

The only time these two shared a ring was at the 88′ Olympics. Photo Credit: Manny Millan

Let's go back in time to Halloween of 1992. In a WBC heavyweight title eliminator, Lewis faced off against Donovan “Razor” Ruddock. The winner here would become the WBC mandatory to face the winner of the Evander Holyfield-Riddick Bowe fight that was taking place two weeks later. Lewis would take Ruddock apart handily in two rounds. Bowe would win a twelve-round unanimous decision against Holyfield to become the undisputed heavyweight champion.

Also, let's recall that ESPN's Sportscenter was the only go-to national sports program at that time. This program was watched over and over again by sports fans. A few weeks later, Bowe would discard the WBC title belt in a garbage can in a staged press conference of which highlights (particularly the placing of the belt in the garbage can) were played at nauseum on Sportscenter for weeks.

Bowe made it clear he was not fighting Lewis at that time and moving in a different direction. And all sports fans, not just hardcore boxing fans, were made well aware of this fact. The term “ducking” was thrown around quite a bit in reference to Bowe's refusal to face Lewis.

Lewis and his management, let's say, added a little gas to what was initially a small fire. This fight became huge in a matter of weeks. Every sports fan wanted to see it.

But Bowe's team had zero interest in facing Lewis. Look at who Bowe fought in his first two heavyweight title defenses. Michael Dokes, a well-faded former heavyweight title belt holder and a career journeyman in Jesse Ferguson. The idea was clearly to make as much money taking as little risk as possible in Bowe's career, and well, Lewis represented simply way too much risk.

Bowe's career would flame out relatively quickly. After those two easy title defenses, he would lose a rematch to Evander Holyfield. After a reset that included winning a rubber match with Holyfield, Bowe would find himself in the ring with a relatively then unheralded Andrew Golota. We all know what happened there and also in the rematch. Just as important, those two fights showed how much Bowe had slipped, and he had gone from being in his prime to being completely shot almost overnight.

Photo by Mikey Williams for Top Rank via Getty Images

While Bowe's downfall was quick, Lewis' was headed in the other direction. He no longer needed Bowe in the second half of the '90s as Lewis was fighting on a much higher level (and Bowe was utterly shot). And thus, the fight never happened.

Mike Tyson – Buster Douglas 2

I remember watching Buster Douglas upset Mike Tyson in February of 1990 with my dad, and the first comment he made to me was that we'd see a part two by the summer. I think many boxing fans probably thought the same thing. Well, an immediate rematch never happened.

Later that year, Douglas would lose the heavyweight title to Evander Holyfield in an abysmal performance. Douglas would then step away from the ring.

Tyson would rattle off four straight wins and appear to be on his way to fighting Holyfield in 1991 to recapture the title. But before that fight happened, Tyson found himself in legal trouble and shortly thereafter behind bars.

Tyson came back in August of 1995 with a quick knockout of Peter McNeeley. Douglas returned a year later with a TKO win against journeyman Tony LaRosa. With both Tyson and Douglas back, there was some thought that they may be on a future collision course.

Even as both suffered setbacks in their ring returns, talk of a rematch seemed to gain more and more steam. Tyson had, of course, lost twice to Evander Holyfield but was once again on the comeback after a fifth-round knockout of Frans Botha in January of 1999.

Mike Tyson and Frans Botha faced off in January 1999 in hopes to regain Mike's image.

Douglas had been utterly destroyed in one round by Lou Savarese in June of 1998. But Douglas bounced back with two wins to get his comeback back on track going into the first part of 1999.

And then the rumors began. Tyson's camp was seeking a “safe” opponent for his next fight. One preferably with a name. Guess whose name was prominently rumored? Yes, James “Buster” Douglas. Some in the sport say the fight was essentially signed, but Douglas backed out at the eleventh hour. Others say it was never really close but briefly discussed between the camps before being scrapped. Some say Douglas priced himself out at initial talks. Others that Tyson's people just “kicked” the idea around for a second before quickly dismissing the notion. What is the truth? Who knows, but it never happened, and unless Triller reenacts the idea (unfortunately not entirely impossible), the once almost certain rematch between Mike Tyson and Buster Douglas just never happened.

George Foreman vs. Larry Holmes

If you are like me and started watching boxing in the late '80s, you remember seemingly seeing either George Foreman or Larry Holmes in a televised fight in what seemed like every week. Okay, I am exaggerating just a tad, but these two were constantly finding their way into the living rooms of millions of Americans in the '80s and '90s. So, it just seemed likely that with so much exposure, they would meet in the ring in what would be quite the highly anticipated event.

Well, it almost did happen, as a matter of fact.

Foreman and Holmes agreed to meet at the Astrodome in Houston, TX, on January 23rd, 1999. The date was important on the sports calendar as it was one week before the Super Bowl with no major competition (remember, of course, in those days, UFC was not around). It figured to be a major event even as boxing fans bemoaned (sound familiar?) about having to fork over PPV dollars to watch these two well past their prime heavyweights square off the event figured to draw lots of eyeballs.

But event organizers failed to deliver a key payment to Foreman by December 31st, 1998, and on New Year's Day, Foreman proclaimed the fight off. That was it.

This is as close Foreman and Holmes got to an actual fight.Photo Credit: Timothy A. Clary/AFP via Getty Images

Holmes always seemed interested in finding a way to get Foreman in the ring. But Foreman never really seemed that into the fight and perhaps saw it more as business opportunity more than anything. Foreman seemed to have had it once and for all with boxing, coming off the Shannon Briggs controversy and now having dealt with more shady characters in the sport who failed to deliver on promises made.

Foreman would never fight again while Holmes continued on for a little while longer before calling it a career after beating Eric “Butterbean” Esch in 2002. But the once seemingly inevitable match between popular former heavyweight champions just never materialized.

Felix Trinidad vs. Terry Norris

In 1996 Felix Trinidad was an upcoming star with an undefeated record who held a welterweight title belt. He had a multimillion-dollar personality and smile. And not to mention one vicious left hook amongst his arsenal of tools inside the ring.

Fighting one weight class above welterweight was 154-pound title belt holder Terry Norris. Norris, by this time, was a well-known name in boxing and still fighting at a high level. Trinidad had fought same decent opposition but not yet found himself in that super fight. With both being promoted by Don King and Trinidad needing that big fight to launch his career into the next stratosphere, a matchup between the two seemed to be all but certain.

As a matter of fact, each fought on the same cards in separate fights on back-to-back occasions in September of 1996 and January of 1997. The next step was for the two to meet in the ring after this final marination in the summer of 1997.

But with the fight seemingly done, Norris reconsidered his options and sued King backing out of the fight. Norris then signed with rival Top Rank with the idea of pursuing a bout with Oscar De La Hoya. Trinidad fought and knocked out Troy Waters instead in August of 1997 while Norris began his career under the Top Rank promotional banner.

Norris would lose later that year in a shocker to Keith Mullings, and with that, the De La Hoya fight was out the door too. Norris was clearly on the downside and never recovered from the Mullings loss losing two more before calling it a career. Trinidad would keep matching forward with what would also become a Hall of Fame career, but Norris' name would never show on his resume.

Brandon Rios vs. Victor Ortiz

Does this sound like a familiar story in boxing? Two fighters from the same hometown fighting in the same weight class with tremendous talent and hatred for one another. Well, we saw in the '90s between Johnny Tapia and Danny Romero. Eventually, after mountains were moved, Tapia and Romero finally faced off in an epic 115-pound title unification showdown in 1997.

The story of Rios and Ortiz seemed eerily similar to that of Tapia and Romero. Rios, the pure brawler like Romero and Ortiz, had a little more variation to his game like Tapia but certainly wasn't afraid to mix it up when needed. Rios and Ortiz were born in Garden City, KS, and both rose the ranks to hold world title belts. They fought in adjacent weight classes, and did I mention that they very much seemingly dislike one another? Oh yeah, from a fan's perspective, we had been down this road for sure and figured mountains could get moved again to make this fight happen.

But it didn't. One issue perhaps was they hated each other so much that one didn't want to other to make money off their name. Another maybe more reasonable explanation is politics kept the fight from happening. When the fight was hot between 2010 and 2013, Rios fought for Top Rank and Ortiz for Golden Boy. And that was smack dab in the middle of boxing's “Cold War.”

Even when the “Cold War” thawed and even after fighters shifted directions, the match never seemed to gain much traction with the political element out of the way. Both had seemingly faded pretty quickly by the time this happened, and public interest was nearly as hot for the fight in say it had been in 2011 and 2012. My guess is the idea was broached, but maybe the money wasn't nearly close to what either expected, so quickly scrapped. Whatever the reason, these two long-time rivals have never been across the ring from one another in the professional ranks.

Marcos Maidana vs. Lucas Matthysse

Politics may have played a role in Rios-Ortiz not happening. But in no way should politics have played a role in keeping two Argentine sluggers, Marcos Maidana and Lucas Matthysse, from meeting in what would have been one of the most anticipated fights of the last decade. Both were aligned during their prime with Golden Boy, and each advised for at least a little while at a similar time by Al Haymon when fighting under the Golden Boy banner. So, what was the issue? It's actually surprisingly simple.

First, going back in time, let's remember both came to the United States as unheralded underdogs. First Maidana, when he upset Victor Ortiz in 2009 and later Matthysse when he pushed Jab Judah to the limit in losing a controversial decision in 2010. But quickly, each gained the appreciation of boxing fans with their aggressive fan-friendly styles and huge punching power.

Early on, fans were clamoring for a fight between the two. But neither's management ever seen too keen on the idea of matching them together right away. Why? Well, one explanation is that both sides figured the fight could be made at any time and still be just as viable financially with the cult following both had gathered since making their United States debut. The thought being, why fight in, say, 2012 or 2013 when just as much money could be had if they fight in 2017 or 2018 (or another point when both may be at career downturns)?

So, the juicy matchup just kept getting kicked down the road. Until well things happened that just prevented the fight from occurring altogether. Maidana made a lot of money fighting Mayweather twice, and well, it seemed just to say I don't need boxing anymore. And that was that—no dream match between the two.