With “The biggest fight in recent boxing history,” right around the corner there is a lot of speculation about the future of both the winner and the loser of this fight.  Surely Oscar De La Hoya vs. Floyd Mayweather will be a PPV success and generate millions in revenue.  No one can argue that Mayweather will be fighting his biggest challenge to date.  The continuing argument is how just great will Mayweather be considered if he beats De La Hoya and retires for good as he has been threatening.  Sure Pretty Boy Floyd has made millions and really does not have to fight again following May 5, nonetheless, if Floyd wants to go down as an all-time great he has a long way to go…no matter what the outcome of next week.

At the beginning of Floyd’s career he was fearless at junior lightweight  Many questioned his sanity when he called out Genaro Hernandez just seventeen fights into his pro career, but after a one-sided victory Floyd looked to be on top of the boxing world.  He followed up by knocking out Angel Manfredy (back when Manfredy was a serious contender) and showed no fear in superfights against Diego Corrales, Jesus Chavez and Carlos Hernandez.  Floyd quickly became one of the hottest commodities in boxing with these victories.  Some criticized him for not fight Joel Casamayor or Acelino Frietas, however, the criticism did not stick due to Pretty Boy’s already-tough resume of fights.

Throughout Mayweather’s rise he had promotional problems several times threatening to sit out his contract.  As it would come to pass, Floyd would stay active in his career and continue to fight tough competition. An eventual move to lightweight put Mayweather in front of Jose Luis Castillo.  In their first encounter Mayweather showed vulnerability first the first time in his career as Castillo proved he could pressure Mayweather, control the action and neutralize his speed.  A good majority of people who watched the fight thought Castillo won the fight.  Thus a rematch was in order and Mayweather clearly won the fight.  Floyd would go on to defend his lightweight crown twice more against limited competition before moving up to junior welterweight and never fought any other lightweight titleholders such as Stevie Johnston or Paul Spadafora.

Floyd’s decision to move up to 140 after four 135-pound title fights was questioned for a brief moment when DeMarcus Corley stunned him in the fourth round but those barbs too would come to pass, because Mayweather went on to floor Corley twice and win an easy victory. In hindsight Corley belongs in the category of safe opponent for Mayweather to move up against.  Floyd would follow by fighting a softball opponent in Henry Bruseles where he gave his football playoff predictions in the middle of the round to the announcers.  Next came Floyd’s PPV debut against the action star in Arturo Gatti, big business after Gatti’s trilogy with Mickey Ward.  Despite being a titleholder, Gatti looked to be the fifth straight “opponent” for Pretty Boy Floyd.  The only people who did not see the one-sided whipping that would play out were the Gatti faithful in Atlantic City.  With Vivian Harris’ shocking loss on the undercard of the Gatti fight and recent 140 champion Ricky Hatton claiming he was not ready to fight Mayweather, Floyd had no other choice but the move up in weight again to search for new challenges. 

In his arrival at welterweight Floyd fought someone who used to be a very good fighter in Sharmba Mitchell…a few years past Mitchell’s best days.  Floyd carried his impressive speed and perhaps some of the power he had at lower weight divisions.  It was clear Floyd was going to be all business at 147.  Floyd first called out Winky Wright the 154 champion, but put several conditions on weight and that fight never happened.  From the moment he stepped up he was stalked by Antonio Margarito and Bob Arum which Mayweather shrugged off claiming low interest in the fight from the boxing public.  Finally he decided to fight Zab Judah who was coming off of a loss to Carlos Baldomir.  Despite the loss, Judah was though to be the biggest test to Mayweather’s career since the Castillo rematch.

Judah came in and was competitive for the first few rounds, nonetheless, the brilliance of Mayweather shined through as the fight wore on.  Floyd captured his fourth world title, a paper IBF title, in as many weight divisions and put himself on top of the pound for pound heap.  Floyd would become the real welterweight champion late last year by defeating Carlos Baldomir. 

Mayweather’s legacy as being one of the best fighters in his era is clear.  He has an excellent case to being considered one of the best junior lightweights.  Nonetheless he falls short of being considered in the top 30 fighters of the last 50 years.  Fighting and beating Oscar De La Hoya helps his case by winning his fifth world title in as many weight divisions and beating a fighter that will also go down as one of the best in this era of boxing.  One has to ponder though…Was Floyd Mayweather Jr. a great fighter or a great businessman?

For the span of four years (close to half of his career) Floyd fought mediocre competition and only two fighters, Corrales and Castillo, who was given a serious chance at beating him.  Floyd left the junior lightweight division as Joel Casamyor and Acelino Freitas were coming into the spotlight.  Moving up to lightweight Floyd fought the best lightweight at the time but moved up without unifying.  At junior welterweight there was really only one fighter who would have made sense after Gatti and that was Hatton (to Floyd’s credit Hatton refused the fight while entangling himself from promoter Frank Waren).  At welterweight there really is only one fight he has utterly avoided and that was Antonio Margarito.  After fighting De La Hoya there really is only a couple of what would be considered superfights for Mayweather, Shane Mosley and Ricky Hatton and maybe Winky Wright, although Wright continues to get heavier.  There are several good fighters who would have a reasonable chance at beating Mayweather such as Margarito,  Kermit Cintron and Paul Williams.

Is it fair that Mayweather is criticized for his choices in competition considering he did fight some of the best available to him?  Why would he retire after he finally became the pound for pound best and could build a legacy as a great fighter? Floyd has made millions and is about to see an eight figure payday.  That alone would make 99% of the world’s population reconsider being punched for a living.  Perhaps there are good fighters that would be good competition for Floyd, but the money would not be there to make them worthwhile and perhaps the challenge in Floyd’s mind would not be there.  And what if he loses to one of these young lions?  Could he rebound from a loss to a young Paul Williams or Kermit Cintron?  How far down would he fall if he lost to Shane Mosley or Ricky Hatton?  Maybe Floyd is right to get out while he still has his brain intact.  Maybe all the money he has made fighting and with endorsements is enough to call it day.  The questions that surround Floyd and this decision to retire after De La Hoya prove that he may not go down as an all-time great fighter…but he is pound for pound one of the best businessmen in the game.