Let me start by saying that I’m actually a fan of Floyd as far as skill and athleticism go, but it’s not a stretch at all to say that he choose his fights carefully, most certainly in the latter half of his career.

Some might call it cherry picking, but he fought the people that made the most sense to him at the time. He fought plenty of really good fighters, so i’m not knocking him, but I’d like to just list some of the names that I think would have had the best chance at beating Floyd.

5. Antonio Margarito

Potential Fight Dates: 2007-2009

The whole issue of Margarito’s loaded gloves leaves a stain on his legacy forever because we simply don’t know how long he may have been cheating. Nevertheless, he was a slow-rolling tank of a boxer, with an iron chin and high workrate as the fight went on. He was also huge for a 147 lb welterweight, being a natural middleweight who cut a lot of weight to make the limit.

How would Floyd have fared against Margarito? The speed and skill advantage is undoubted but Margarito would probably be the biggest guy Floyd ever faced on fight night if they two were fighting at 147. Floyd would be able to land shots at will just as Shane Mosley did, but he doesn’t have the power to even put a dent in his chin.

I would still favor Mayweather if the fight would have taken place but it wouldn’t have been as easy as his win over Baldomir for example. The size and pressure of Margarito would have tested him for sure.

4. Paul Williams

Potential Fight Dates: 2007-2008

Paul Williams in his prime was a tough style match up for almost anyone. He was extremely tall for a welterweight, was a southpaw, and had an very high work rate. Floyd never really faced anyone similar to Williams because of the simple fact that there wasn’t anyone else like Williams. His awkward style would have been something Floyd had never really experienced before.

Yes, Williams did get outboxed by Carlos Quintana, but that wasn’t Paul at his best and the rematch showed that. I would call Floyd Mayweather vs Paul WIlliams a 50/50, I really think Paul would have given him that much trouble.

3. Shane Mosley

Potential Fight Dates: 2004-2005

Obviously Floyd Mayweather fought and beat Shane Mosley in 2010, but if the fight have been about five years sooner, it could have been far different. This would have required that FLoyd basically skip his short run at 140 and move from lightweight to welterweight, which might be asking for a lot in this hypothetical matchup.

Their actual fight gives a good indication of the trouble that Shane could have given him. Shane probably came close to knocking down or possibly finishing Floyd that anyone else in his entire 49 fight career. Mosley seemed to have the hand speed advantage but Floyd adapted as he always does and went on to dominate Mosley.

I would give this another 50/50 outcome. This version of Shane might have just been too much offensively with his hand speed, and maybe Floyd didn’t totally perfected his shoulder roll defense at this period of time.

2. Amir Khan

Potential Fight Dates: 2011-2015

This one is another bit of a stretch since Khan didn’t move up to welterweight until 2011, but I firmly believe that Khan would have had a speed advantage over Mayweather that could have potentially been too much for him. Floyd is clearly the superior fighter as far as skill goes, but he doesn’t have the pop to have taken advantage of Khan’s chin. Yes, Floyd always adapts, but Khan can maintain his speed for the whole fight and box beautifully when he finds his rhythm. The later in Floyd’s career this fight would have happened, the more I lean towards Khan, so I’ll say 60/40 for Khan.

1. Manny Pacquiao

Potential Fight Dates: 2007-2009

This was the biggest fight in recent boxing history, and in regrettably failed to live up to it’s hype. Floyd’s win was a solid one for the purists out there, but many people were disappointed at a fairly boring fight. Everyone knows that this fight should have taken place about 7 years sooner than it did, and outcome could have changed dramatically.

In 2007-2009 this fight would have been at both guy’s peaks. I would have to slightly favor Floyd, but the prime version of Manny was so electric he was capable of beating pretty much anybody. This was the best fight that could have happened in boxing had it been signed and sealed years earlier, but the negotiations just went on and on. It’s a shame but at least we got the fight finally at some point.

As I said earlier, this post is not intended to bash Floyd directly or to even criticize his choice of opponents, I’m merely offering my opinions on who would have given the future hall of famer the most competitive fight.

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