The 10 biggest boxing ‘what ifs’ of the last 30 years: Mayweather vs. Pacquiao

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…