15 Kinds Of Fight Fan Heartache

Boxing, by its very nature, is the sport of heartache and disappointment. More than any other, it sadistically toys with its fans, raising expectations and then, as often as not, dashing all the excitement and anticipation to smithereens on the jagged rocks of fate. Lacking structure, or even a semblance of authority, the most promising matches so often simply fail to be. With the news that, once again, the must-see clash in the welterweight division, Terence Crawford vs Errol Spence Jr., has slipped through our fingers, fans have been reminded of this cruel truth.

And so there is no better time to reflect on other instances of what we might call “fight fan heartache,” and remind ourselves that, like it or not, this is just how it goes in the chaotic enterprise called the fight game. Herewith, fifteen other match-ups that never were, all of them speaking to pugilism’s inability to fulfill its true potential. Some lessons to be learned here, though it would be foolish to expect different in the future. But, as all true fight fans know, hope does indeed spring eternal.

Is Joshua vs Fury destined to never be?

The Ones That Got Away
Lennox Lewis vs Riddick Bowe: This is surely the most infamous heavyweight non-event of recent times. Lewis had stopped Bowe in the 1988 Olympic final, and by the early 90’s the two appeared on a collision course. But after Lewis destroyed Razor Ruddock in two rounds and Bowe took the undisputed championship from Holyfield, Big Daddy’s team made an extortionate 90-to-10 purse split demand and when Lewis refused, Bowe dumped his WBC belt in a trash can. Later, Lewis’ surprise defeat to Oliver McCall scuppered another planned bout, and the fight was finally killed off for good when Bowe retired following his pitiful performances against Andrew Golota in 1996.

Bowe and Lewis: They locked-up at the Olympics, but not in the pros.

Roy Jones Jr. vs Dariusz Michalczewksi: There are two types of boxing fans: those who refer to Jones as the former “undisputed” light heavyweight champion, and those who know he never really was. Despite being the world’s best pound-for-pound boxer, “Captain Hook’s” reluctance to travel abroad after his dreadful Olympic experience in Korea, combined with Michalczewksi’s contentment to defend his lineal crown only in Germany, meant the American never actually faced his most significant rival. And while few would have picked against a peak Jones, a win would have cemented Roy’s status as the best light heavyweight on the planet.

Roy is a latter day great, but there’s something missing on his record.

Felix Trinidad vs Ike Quartey: For several years “Tito” Trinidad and “Bazooka” Quartey were both undefeated champs in a stacked 90s welterweight division. Both could box and bang, with Quartey carrying one of the best jabs in boxing and Trinidad bringing one of the most devastating left hooks. It’s easy to imagine the styles blending beautifully in this one to produce a top-drawer contest of technical skill and explosive punching. It would have been fascinating to see who might have prevailed, but sadly, despite the fight almost being sealed at one point, politics and Don King meant it never came to fruition.

Felix Trinidad

Juan Manuel Marquez vs Erik Morales: The spectacular Barrera-Morales-Pacquiao-Marquez round-robin delivered some absolute classics, and this Mexican civil war would almost certainly have added another one to the collection. Unfortunately, although their careers did overlap, their respective peaks didn’t quite match: while Morales was blazing a trail in the late 90s, Marquez was struggling to gain recognition. And by the time Marquez was really hitting his stride, the career of Morales was winding down.

Juan Manuel Marquez. Painting by Damien Burton.

Manny Pacquiao vs Edwin Valero: Tales of how well Valero acquitted himself in the gym versus some of the world’s best fighters fueled the Venezuelan’s almost mythical reputation, and his perfect KO record further bolstered his image as one of boxing’s most formidable forces. Meanwhile, Pacquiao tore through every division from featherweight to welterweight in probably the most impressive run in modern boxing history. With Valero steadily climbing the weights after him, an explosive meeting between the pair was almost inevitable. That is until Valero murdered his wife in 2010 and then committed suicide while in police custody.

Marquez and Pacquiao: Would Valero vs “The Pacman” been even better?

Unfinished Business
Oscar De La Hoya vs Felix Trinidad: On paper Oscar vs Tito was a dream superfight, but after weeks of anticipation and hype, neither man rose to the occasion. And in addition to the tepid action, controversy over the judges’ verdict only compounded the sense of disappointment. A rematch at 154 pounds with both looking to redeem themselves would have helped settle the argument and likely given fans a much more entertaining scrap. The fact that it never happened is an absolute travesty, and both must surely look back with regret for letting personal pride over the purse split take precedence over giving boxing a fight to remember.

Oscar and Felix owed fans a rematch.

Pernell Whitaker vs Julio Cesar Chavez: The word “robbery” gets thrown around a lot in boxing, and most of the time it’s a huge exaggeration. But not here. In a fight between two all-time greats, the world saw Pernell Whitaker outbox fellow champion Julio Cesar Chavez over 12 rounds in September of 1993. Despite the judges’ defying the obvious and ruling the bout a draw, the performance cemented Whitaker’s status as the best boxer on the planet, pound-for-pound. And while the judges’ verdict is baffling, equally mystifying is the fact Chavez and Whitaker never had a return to put things straight.

The judges said otherwise, but Whitaker clearly got the better of Chavez.

Marco Antonio Barrera vs Naseem Hamed: A lot of boxing fans reveled in Naz’s humbling at the hands of Barrera. The cocky Englishman talked a big game, and for a long time he backed it up, but he met his match in a disciplined, masterful performance from Barrera. “I’ll come back and beat him,” promised Naz in his post-fight interview. For those fans who had followed the Prince throughout his career, Hamed’s failure to even try and even the score was almost more disappointing than the defeat itself. Instead of invoking the rematch clause, he took a year out, looked awful in a single comeback performance, and then faded into obscurity, leaving us to wonder what might have been.

Prince Naseem Hamed: Ink drawing by Damien Burton.

Chris Eubank vs Nigel Benn III: After Eubank stopped Benn in a titanic struggle at 160 pounds in 1990, they rematched three years later in a super middleweight unification fight in front of some fifty thousand fans. At the end of another engrossing struggle, most thought Eubank lucky to earn a draw and escape with his belt; Benn was devastated. A third fight would have been epic and looked like a no-brainer, but it never came off. Their battle as Roman gladiators years later was entertaining television, though hardly an adequate substitute.

Eubank and Benn rumble.

Roy Jones Jr. vs James Toney: When they met in 1994, Toney was the IBF 168 pound champion and regarded as one of the best fighters in the world, yet Jones made his unanimous decision victory look easy. Some said Toney’s lack of discipline and the subsequent battle with the scales had cost him the fight and afterwards his career stagnated while Jones excelled. By 2003 “Superman” had claimed a version of the heavyweight title and Toney was also back in form, having re-established himself as the IBF cruiserweight champ. A rematch between them around that time would have been fascinating, but the chance passed by when Jones moved back to 175 and was knocked out by Antonio Tarver, thus losing both his titles and his aura of invincibility.

Right Fight, Wrong Time
Floyd Mayweather vs Manny Pacquiao: In late 2009, Pacquiao stopped Miguel Cotto to earn a seventh divisional title and wide recognition as the Fighter of the Decade. His only competition for title of the world’s best boxer was from Mayweather, the former pound-for-pound king who’d recently returned from a mini-retirement. A fight in early 2010 was the perfect match at the perfect time, rivaling any in modern history in terms of pure pugilistic pedigree. But after Pacquiao refused to cave to Mayweather’s drug-testing demands, it sparked years of finger-pointing and tiresome rounds of “he said, she said” in the media. When they finally met in 2015, it was better late than never, but the bout itself was devoid of both action or drama.

Floyd vs Manny: way past its “best before” date.

Lennox Lewis vs Mike Tyson: Tyson’s trainer Cus D’Amato famously prophesized that the two would one day meet for the championship of the world. He was right, but it came almost a decade too late. First, Tyson’s stint in prison in the early 90’s got in the way. Then, after regaining the WBC championship in 1995, Tyson opted to pay Lewis four million in “step-aside money” so he could fight WBA champ Bruce Seldon instead. “Iron Mike” then vacated the WBC belt rather than defend against Lewis, and was subsequently beaten by Holyfield. When they finally fought for Lewis’ titles in 2002, it was still a massive event, but by then Tyson was a shell of his former self.

Lewis hammers Tyson.

Mike Tyson vs Evander Holyfield: The best-laid plans go awry, as they say. At least, they do if you schedule a Tyson vs Holyfield, multi-million-dollar showdown, but forget to send the memo to James “Buster” Douglas. Tyson had agreed to meet Holyfield in 1990 and he had to do was get past a 40-to-1 longshot. But Douglas shocked the world, wrecking the planned mega-fight. Tyson and Holyfield did finally meet in 1996, and this time it was Evander’s turn to shock the world. Many will argue Holyfield always had Tyson’s number, but who can really say what would have happened if Douglas hadn’t got in the way?

“The Real Deal” vs “Iron Mike.”

Roy Jones Jr. vs Joe Calzaghe: The long and sometimes disappointing reign of super middleweight champ Calzaghe was eventually punctuated with fine wins over Jeff Lacy and Mikkel Kessler, and he ended his career by scalping two great American names at light-heavyweight in Bernard Hopkins and Roy Jones. But while both wins were welcome additions to the Welshman’s record, they could have meant so much more had they taken place a few years earlier. The fight was mooted in 2002, and Jones even called out Calzaghe after defeating another Brit, Clinton Woods, but then opted to challenge himself at heavyweight instead. By the time they fought in 2008, Jones, at 39 and after two knockout defeats, was a much diminished fighter.

Roy and Joe mix it up.

Bernard Hopkins vs Roy Jones Jr. II: Hopkins and Jones first met for the vacant IBF middleweight championship in 1993, a fight Jones won via clear decision. By 2002 they were widely regarded as the best two fighters in the world, with Jones holding most of the belts at 175, Hopkins at 160. Given the standing of both, a rematch seemed only natural. Instead, after both defended their belts in separate locations on the same night, fans were treated to a shouting match over the HBO airwaves, refereed by Larry Merchant. Jones insisted on a bigger piece of the purse, but Hopkins refused, and the fight didn’t happen. When they eventually did rematch in 2010, it was a sad spectacle: both were in their fifth decade and Roy’s once dazzling skills were shot to pieces.             

— Matt O’Brien 

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