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Floyd Mayweather is one of the best boxers of all time. While not adored by many, it's nearly impossible for even the staunchest Mayweather detractor to deny his greatness in the ring.
Having fought the best of his era, Floyd 'Money' Mayweather retired with a perfect undefeated record of 50-0. This unblemished resume is filled with some of the mightiest names from the last twenty-five years. Manny Pacquiao, Canelo Alvarez, Miguel Cotto, Oscar De La Hoya, Shane Mosley - Mayweather conquered some of the best fighters the sport had to offer.
With such a stellar and spotless record inside the ring - and being one never to shy away from playing the ultimate villain - it's become something of a pastime for hardcore boxing fans to think of possible opponents that could've defeated Floyd Mayweather.
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Having fought champions across five different weight classes, Mayweather could have theoretically competed against many legends had he been born in a different era. This list will examine five fighters from Mayweather's generation and some from earlier eras who may have had a chance at usurping the defensive genius.
Without further ado, these are the five men who could've defeated Floyd Mayweather:
#5. 'Winky' Wright would've been a terrible opponent for Floyd Mayweather at 154lbs
When talking about some of the most avoided fighters in the sport's history, it would be a crime not to mention Ronald 'Winky' Wright.
A defensively sound southpaw, Wright was notorious for always keeping his gloves raised high and fighting behind an ultra-tight guard. Possessing a stiff jab and iron chin, 'Winky' could be a nightmare to deal with when he was on the front foot.
Wright's greatest success came in the light-middleweight division (154lbs). During his time in the weight class, he was able to capture multiple championships. However, his most significant moment came when he defeated Shane Mosely twice in 2004.
In one of his first outings against a top star in the sport, Wright dominated 'Sugar' Shane in both of their fights. Mosley, who is roughly the same size as Mayweather, could not keep Wright off him. 'Winky' was able to walk through Mosley's best shots and overpower him on the inside and outside.
Mayweather had tremendous success at 154lbs. He had three championship outings in the weight class, having conquered Miguel Cotto, Oscar De La Hoya, and an undefeated Canelo Alvarez.
Against 'Winky', however, 'Money' would have had to contend with a taller southpaw who equaled him in reach. While fighting behind his signature tight guard, Wright would have patiently stalked forward, not giving Mayweather many opportunities to fire his patented right-hand counter.
In his first bout at 154lbs, 'Money' was troubled early on due to Oscar De La Hoya's stiff jab. However, De La Hoya quickly abandoned the punch and relied on crowd-pleasing combinations instead. Wright loved the jab, and it would have been difficult to pull him away from his favored punch.
Interestingly, according to a 2005 ESPN article by Steve Kim, there were negotiations for a Wright-Mayweather bout. However, Bob Arum, who was Mayweather's promoter at the time, rejected a 50-50 deal for the fight purse at the last minute of negotiations. Arum, a veteran promoter, could have possibly seen just how much of a nightmare 'Winky' Wright would have been for his top fighter at the time.
#4. Roberto Duran could've beaten Floyd Mayweather at 135lbs
Roberto Duran is one of the greatest legends of the sport. 'Hands of Stone' cemented himself as a boxing icon by battling the best of the best.
Although the Panamanian's main claim to fame was his spectacular hard-fought victory over a prime 'Sugar' Ray Leonard in 1980, where he won the welterweight crown, his true prime took place in the lightweight division (135lbs) years prior.
At 135lbs, Duran was an absolute monster. Equipped with slick upper-body movement and favoring a swarmer style that exhausted his opponents, 'Hands of Stone' carved through the lightweight division for the majority of the '70s. Some of the best names on his 135 resume include Leoncio Ortiz, Esteban de Jesús, Ken Buchanan, and Hector Thompson.
At welterweight, where Mayweather dominated for the second half of his career, Duran would have been at an immense disadvantage in terms of weight. However, at 135, 'Hands of Stone' would have been more than a match for Mayweather.
Floyd Mayweather fought in the lightweight division from 2002 to 2003. During this timeframe, Mayweather, who went by the moniker 'Pretty Boy', had arguably his toughest fight. On April 20, 2002, Mayweather fought Mexican champion Jose Luis Castillo for the WBC Lightweight Title.
In a back-and-forth bout that saw both men find success, 'Pretty Boy' came out with a tight unanimous decision victory. To this day, many fans believe Castillo won the fight.
It's hard to imagine Duran not finding the same success that Jose Luis Castillo captured. 135lbs was his realm, and Mayweather still had not perfected his defense-reliant style at this weight class. 'Hands of Stone' would have found ways to pull Floyd Mayweather into a firefight and, in the process, perhaps found a way to win.
#3. Sergio Martinez would have been Floyd Mayweather's most awkward opponent
Sergio Martinez was an athletic southpaw who possessed phenomenal stamina. A volume puncher who liked to move and had just enough pop in his punches to keep his opponents honest, 'Maravilla' was a frustrating puzzle to solve between the ropes.
Prior to taking the middleweight (160lbs) crown against Kelly Pavlik in 2010, Martinez spent a good portion of his career fighting at 154lbs. Although Martinez's main championship success came at middleweight, the Argentine was never considered big for his weight class. In fact, 'Maravilla' was often noticeably the smaller man in many of his bouts.
Floyd Mayweather would have had to contend with Martinez's reach and find ways to halt the Argentine's movement. Simply put, a fight against 'Maravilla' would have been one of Floyd Mayweather's greatest challenges.
A fleet-footed southpaw with long arms and an endless gas tank is a tough fight for anyone, even for a boxing professor like 'Money'.
#2. 'Sugar' Ray Leonard could match Floyd Mayweather's speed
'Sugar' Ray Leonard is one of the greatest welterweights of all time. Blinding speed, explosive power, and swift feet that allowed him to glide around the ring, Leonard possessed a dangerous toolset that made him a constant threat.
A boxer-puncher who could mix it up on the inside or outside, the Olympic gold medalist always found a way to win, no matter what style or opponent he was up against.
Leonard danced around the ring in his famous No más rematch against Roberto Duran and frustrated his rival with swift one-twos until Duran quit in the eighth round. In 1987, after years away from the sport, Leonard did the impossible and moved up in weight to defeat middleweight king Marvin Hagler. Leonard won the contest by stealing the judges' attention with his outrageous hand speed and flashy combinations.
In his most dramatic bout, Leonard battled Tommy 'Hitman' Hearns in 1981 in a welterweight unification clash. 'Sugar' Ray entered the fight perceived to be the better technical boxer. However, as the hard-fought battle dragged on, it was evident he was struggling with Hearns' immense reach. Down on the scorecards, with legendary trainer Angelo Dundee shouting: "You're blowing it now, son! You're blowing it!" Leonard was forced to bite down on his mouthguard and throw the textbook out the window.
In the 14th round - championship fights were still 15 rounds - Leonard rocked his rangy opponent with an overhand right. With 'Hitman' on the ropes, Leonard launched a brutal combination, forcing a referee a stoppage and earning one of his most iconic victories in the process.
Floyd Mayweather would have had a long night at the office against 'Sugar' Ray. Leonard was a fighter who could've matched Mayweather's speed, agility, and precision. Like Floyd Mayweather, Leonard had encountered many different styles and could make adjustments in the heat of battle. Interestingly, 'Sugar' Ray fought Mayweather's father in 1978 and secured a 10th-round TKO victory, giving him a taste and glimpse of the family's defensive capabilities.
#1. Thomas 'Hitman' Hearns would have been the ultimate nightmare for Floyd Mayweather
Tommy Hearns would've been the worst opponent for Floyd 'Money' Mayweather.
Standing at 6'1 and possessing a reach of 78in, 'The Motor City Cobra' was a nightmare to deal with on the outside. Equipped with one of the most destructive right hands in the history of boxing, 'Hitman' was able to lay out his opponents with sniper-like accuracy.
Against Hearns, Mayweather would find himself in a position he rarely encountered; he would be the shorter man with the shorter reach.
The late great trainer Emanuel Steward, who helped shape Hearns into the destroyer he was, believed that technical boxers never gave his pupil the trouble that brawlers and punchers did. Understandably, it's hard to outbox a man with Hearns' reach and height.
A lethal right hand wasn't the only weapon in Hearns' arsenal. Utilizing what pundits now call a "flicker jab," 'Hitman' maintained distance and kept his opponents on the backfoot with a sharp left hand. The jab kept his opponents guessing and helped hide his bazooka of a right hand.
'The Motor City Cobra' would have put Mayweather through hell. Against Hearns, Floyd Mayweather would have had to overcome a significant size and reach disadvantage. He would also have to fight a legend with outstanding boxing fundamentals.
To top it all off, for twelve whole rounds, he would have had to avoid one of the most dangerous punches in the sport's history.
