Boxing, by its very nature, is the sport of heartache, disappointment and painful memories. 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 cruel fate. Lacking structure, or even a semblance of authority, at the black heart of pugilism chaos reigns. So often the match-ups that are most promising, the can’t-miss opportunities for fans and participants alike, simply fail to be. No other sport can conceive of not having the best compete against the best. After all, that’s why playoffs and tournaments exist.
Surveying the 2019 boxing landscape, there are some brilliant match-ups to be made. Spence vs Crawford at welterweight; Lomachenko vs Garcia at lightweight; a round-robin between Wilder, Fury and Joshua at heavyweight, and a much-needed Canelo vs Golovkin trilogy fight at middleweight, just to name a few. But whether we will ever get to see any of these duels is another question entirely. So it is in boxing, and so it has always been.
You may think that the powers-that-be would be fools to let Crawford vs Spence or Joshua vs Wilder slip through their fingers. You may think that everyone will, before it’s too late, come to their senses and make the match-ups that all of boxing can’t wait to see. Think again. As recent history will attest, pugilism has a unique talent for shooting itself in the foot. And then reloading the shotgun and blasting away again. Reflecting on this truth has caused me to look back over my three decades of being an ardent fan of “The Sweet Science” and dredge up some painful memories. Here are fifteen match-ups which speak to pugilism’s inability to ever truly fulfill its potential.
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.
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, Jones’ 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.
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.
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.
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.
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.
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.
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.
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.
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.
Lennox Lewis vs Mike Tyson: Tyson’s trainer Cus D’Amato famously prophesized that the two would one day meet for the heavyweight championship of the world. He was right, but it came almost a decade too late. First, Tyson’s stint in prison in the early 90s 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.
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?
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.
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 men 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 men were in their fifth decade and Jones’ once dazzling skills were shot to pieces. — Matt O’Brien