The 10 biggest boxing 'what ifs' of the last 30 years: Mayweather vs. Pacquiao in 2011 leads the way

With the unprecedented coronavirus outbreak pushing the return of professional boxing in the United States back until at least June, the hiatus has given fans and pundits a chance to reflect on the sport's recent history. 

Boxing has long lent itself to the type of barber shop arguments that compare the greatness of fighters from different eras and who would win in a mythical matchup. But the current break in the action has also allowed the hard-core faithful to ponder the great what if's of recent memory. 

To help further stoke the fire of debate, we looked back at a number of potential scenarios over the last 30 years to ponder how the future would've been different had the results of the past been slightly edited. 

1. What if Floyd Mayweather and Manny Pacquiao had fought in 2011?

The biggest superfight of the 21st century gave us a meeting between the two best fighters of their weight class, era and pound-for-pound ranking at the time in 2015. The problem, however, was that Mayweather was 38 and Pacquiao was 36 by the time their five-year soap opera finally consummated. The fact that the welterweight stars turned in a tentative, technical bout instead of the go-for-broke classic many casual fans had expected left many wondering how different it would've looked when both were in their primes. By 2011, Pacquiao had announced himself as a legitimate welterweight force with almost other worldly speed and explosion from awkward angles. But let's give Mayweather the respect he deserves as one of the greatest defensive strategists in boxing history and assume he wouldn't get steamrolled. 

Mayweather's unbeaten career was defined by the championship adjustments he made each fight after taking an early snapshot of his opponent's style. The true question remains whether Mayweather would be able to adjust with enough time to pull out a clear decision. While Juan Manuel Marquez laid out a blueprint on how to time Pacquiao's bursts with hard counter shots, Mayweather was rarely one to punch with his opponents and trade. He would need to find ways to get off first and discipline Pacquiao, similarly to what he expertly did with lead right hands both early and late in their only meeting. Suffice to say, fans would be looking at a contested split decision had the two fought at the peak of their powers. And given his history of great defense nullifying great offense, the "Money" is still on Mayweather. But speaking of Floyd ...

2. What if Mayweather had fought everyone his critics had wanted him to? 

Although it remains hard to poke at the totality of Mayweather's incredible resume, a segment still exists of those who take issue with the timing of each fight. In addition to waiting five years to face Pacquiao (although blame can be shared on both sides), Mayweather fought just three times over a four-year run of his physical prime from 2008-11 and largely avoided the gauntlet of a loaded welterweight division. Although it was early in his rise toward becoming the biggest pay-per-view star in combat sports history, Mayweather had already amassed the type of control over his matchmaking (and more importantly the terms of said fights) that only Sugar Ray Leonard had known. Mayweather also timed "retirements" which allowed him a chance to build his star commercially through such avenues as WrestleMania and "Dancing With The Stars" while resting his chronically injured hands. So what would've happened had he instead faced the likes of Miguel Cotto, Antonio Margarito, (a younger) Shane Mosley, Paul Williams and prime Pacquiao at 147 pounds? First off, Mayweather likely wouldn't have been able to enjoy the incredible longevity he showed late in his 30s by taking on such dangerous fights in succession. Yes, it's easy to imagine Mayweather beating each one on the list in one-off fights (although the idea of him handling Williams' length and volume remains an all-time unknown). But preserving his pristine record by doing so in such a short window of time remains highly unlikely. Mayweather had a strategic method to his madness that is hard not to respect. 

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Mayweather timed his opponents -- and punches -- at the perfect times throughout his career. Getty Images

3. What if history had been kinder to Gennadiy Golovkin?

Whether or not he faces Canelo Alvarez for a third time or if, at 38, he even ever records another victory, GGG will go down as one of the greatest middleweights in boxing history thanks, in large part, to his record-tying 20 title defenses. Yet there's more than ample reason to debate whether the Kazakh slugger could've one day retired as THE greatest had it not been for some bad luck and politics. Golovkin was already 30 and nearly halfway into his 160-pound title reign by the time he made his U.S. debut in 2012. Soon, he became the most avoided fighter in the sport and looked to offset that limitation by staying as active as possible. Although he went on to fight Alvarez twice, he was forced to wait two full years before first doing so as the Mexican star strategically allowed GGG to reach his 35th birthday. Then came the controversial scorecards in both fights (not to mention Alvarez's failed drug test in between). Had Golovkin received the winning nod twice, like many experts believe he deserved, against the best fighter of his era, his unbeaten resume would've been hard to ignore. One can also  imagine where his rank might be had former lineal champs and future Hall of Famers Sergio Martinez and Miguel Cotto not openly avoided him. Critics of GGG would be fair to mention the favorable decisions he earned against Daniel Jacobs and Sergiy Derevyanchenko, as would historians who counter that his title defense streak contains fights for interim and secondary belts which, like the current debacle within the WBA, shouldn't be recognized on the same level. 

4. What if Riddick Bowe hadn't thrown his WBC heavyweight title in the trash in 1992 to avoid Lennox Lewis?

For as much as this has remained a fun topic to discuss over the past three decades, it's hard not to ignore the fact that we might already know the answer. Lewis, who represented Canada, scored a knockout of Bowe in the gold medal match of the super heavyweight division at the 1988 Olympics. Given Bowe's not-so-secret disdain for conditioning, it's not a stretch to imagine his team was strategic in keeping him away from Lewis in order to help Bowe maximize his financial window. Fresh off a breakthrough title win over Evander Holyfield in their first of three meetings, Bowe went on to easy title defenses for big money over Michael Dokes and Jesse Ferguson in 1993 after dumping his WBC title to avoid his mandatory opponent in Lewis. Not long after, the wheels slowly began to fall off for Bowe, who would split his next two fights with Holyfield but end up effectively washed up by age 27 amid wild fluctuations in weight. For everything Bowe brought to the table as a 6-foot-5 puncher with a strong chin and the ability to box at close range, Lewis was just as good or better in almost every category (save for his flash chin) and held a key psychological edge for having previously stopped him. 

5. What if Erik Morales had fought Juan Manuel Marquez in their featherweight primes? 

This wasn't exactly your father's "Four Kings" of the 1980s when welterweight and middleweight stars Leonard, Thomas Hearns, Roberto Duran and Marvin Hagler took over the sport by waging memorable wars against one another. Yet the four-pack of current and future Hall of Fame fighters that operated in and around the 126-pound division in the 2000s -- Pacquiao, Marquez, Erik Morales and Marco Antonio Barrera -- still provided a number of all-time great fights. The only pairing, however, that did not take place among the "Featherweight Four Kings" was Morales and Marquez, and there's a case to be made that it could've produced the best theater of them all. As an expert counter puncher, Marquez would've possessed the perfect antidote to Morales' attacking style. The peak time for the matchup may have been in late 2004 at 130 pounds, had Morales not chosen to complete a trilogy with Barrera. Marquez was fresh off a draw in his first of four meetings with Pacquiao and Morales would begin his trilogy with the "PacMan" the following year. Given the toughness and vulnerability shown at times by each fighter, there's little doubt a highly skilled brawl would've broken out. Considering Morales was operating the tail end of his prime by this point and the late-peaking Marquez had yet to enter his, my money remains on "El Terrible" pulling out a competitive decision. 

6. What if the judges would've sided with Juan Manuel Marquez over Manny Pacquiao? 

It's an interesting thought and one that would've likely derailed the two from ever reaching the heights that their four-fight series ultimately did as the best rivalry of the modern era. Had Marquez, say, edged Pacquiao in their first two meetings in 2004 and 2008, respectively, there wouldn't have been a need for third and fourth fights. There's an equal discussion to be had as to whether Pacquiao would've become the same level of global superstar had he been forced to endure the two defeats. Yet given his exciting style and willingness to rise up in weight so dramatically, there's still reason to believe "PacMan" would've gotten there, with Marquez likely looked at in hindsight as a tough style matchup. With all that said, we should probably credit referee Joe Cortez for making sure this rivalry even exists at all considering he never panicked and allowed their first fight continue despite Marquez getting dropped three times in the opening round before rallying to a draw.

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We may not have needed a third or fourth fight between these two if the cards went differently. Getty Images

  7. What if Roy Jones Jr. had remained at heavyweight after capturing John Ruiz's title? 

Jones, who won world titles in four divisions, never defended the WBA strap he won by outpointing Ruiz in 2003. His hasty return to 175 pounds, following a gutsy decision win over Antonio Tarver in their first meeting, also led directly to his undoing as Jones was knocked out cold by Tarver and Glen Johnson in succession and never reclaimed his greatness. Having bulked up to 193 pounds to face the 226-pound Ruiz, and doing so without losing his trademark speed and athleticism, Jones became an interesting proposition for the division despite being so small. Staying at heavyweight would've meant subjecting himself to the potential of heavy damage, even with the speed advantage he would be able to maintain even as his skills slowly diminished with age. Still, there was an interesting group of smaller heavyweights in prominent rotation at the time, including Chris Byrd and the aging trio of Mike Tyson, Evander Holyfield and James Toney, of whom Jones could've had the potential to make big-money fights against. 

Jones was even, at one point, linked with rumors of possibly facing Lewis in a unification bout in Africa for an ungodly sum of cash. He has said publicly in the ensuing years that outside of a brief flirtation with the idea of fighting Tyson (which his father was against), he never gave staying on at heavyweight a serious thought. It would've required Jones to channel a darker side of himself -- the alter ego he called "RJ," which he famously brought out in his one-round destruction of Montell Griffin in their 1997 rematch -- on a regular basis. Given his sublime skills, however, the idea of him beating any of those smaller heavyweights isn't much of a stretch and might've been enough to catapult Jones, who was never a consistent PPV brand, to an even higher level of stardom. But if you're looking for an even more interesting scenario ...

8. What if Jones had retired and never fought again after conquering Ruiz? 

Talk about a potential debate for the ages. Jones is already one of the greatest fighters to ever put on a pair of gloves. No one is questioning that. But there's something to be said for the very few who have ever walked away on top without ever letting critics see the decline (both Rocky Marciano and NFL legend Jim Brown come to mind). It's a phenomenon that has helped increase the legend of many famous rock stars who have died young before their careers were fully developed. But in boxing, it's possible to argue that no one ever had more "money in the bank" from a critical standpoint than Jones after beating Ruiz for a heavyweight belt at age 34. Asking Jones to walk away at the peak of his commercial prime might not seem realistic. But Jones had both a full-time announcing gig at HBO and a merchandising deal with Jordan Brand at the time. Had he never fought again and retired virtually unbeaten at 47-1 (with the lone defeat coming by questionable disqualification against Griffin), it's not a stretch to say Jones might be in the discussion among the likes of Sugar Ray Robinson and Henry Armstrong for best pound-for-pound fighter in history. Winning titles at both 160 pounds and heavyweight is no joke, with Bob Fitzsimmons remaining the only other fighter in history to do so. But more importantly, Jones would've saved himself historically from ever looking vulnerable or solved. Gone would be his sad knockout losses at cruiserweight around the globe and his hanging on until age 49 by fighting journeymen of all shapes and sizes off of television. 

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Jones could be considered the GOAT had he retired after his heavyweight title win in 2003. Getty Images

9. What if George Foreman and Mike Tyson had actually faced off in the early 1990s? 

Let's not forget, this was actually a thing. The two heavyweights of legendary punching power were featured in separate bouts atop a 1990 HBO card in Atlantic City that was designed to tease a subsequent non-title bout between them in the first legitimate test of Foreman's comeback. Instead, Tyson and promoter Don King took their business to Showtime for a pair of bouts against Donovan "Razor" Ruddock and Tyson would serve jail time soon after for rape. Their respective careers never intertwined again, even with Tyson's re-emergence in 1995 and Foreman's thrilling upset of Michael Moorer the previous year to reclaim the title. Had they met in late 1990, it could've produced an absolute war and one which Foreman couldn't have been counted out of given Tyson's history of coming up short against in-ring bullies. But if we are going to talk Tyson, we might as well hit on ...

10. What if James "Buster" Douglas had been counted out in Round 8 against Tyson?

It has always been an interesting question and one which must come with it a great deal of wishful thinking that a close win over the upset-minded Douglas could've inspired Tyson and his inept team to stop him from an inevitable collapse. Despite losing most of the fight, Tyson floored Douglas with a vicious uppercut two rounds before "Iron Mike" was shockingly finished. Tyson's team spent the aftermath of the bout complaining Douglas benefitted from a long count from Octavio Meyran. Had Douglas not made it to 10, the biggest upset arguably in the history of sports wouldn't have happened. But imagining Tyson could've regained his form of old is a stretch given the chaos surrounding his personal life at the time after King got his hooks in him. Anyone from Tyson's original team who provided stability had been let go. So if Tyson had survived Douglas, one can only imagine a loss to Holyfield in 1991 would've been inevitable. Holyfield would go on to score a massive upset over Tyson in 1996 by standing up to the bully and fighting him on the inside with heavy clinching. It's a style that a much more prime Holyfield could've mixed nicely with his own brand of aggressive boxing in a fight, had they both entered unbeaten, that would've been a blockbuster. 

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Brian Campbell covers MMA, boxing and WWE. The Connecticut native joined CBS Sports in 2017 and has covered combat sports since 2010. He has written and hosted various podcasts and digital shows for ESPN... Full Bio

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