Welterweight – Floyd Mayweather Jr. vs. Antonio Margarito
Best time to make this fight: November of 2006
Reasons: Mayweather was on a roll. His six-round destruction of Arturo Gatti in June of 2005 and victories over a pair of compromised fighters in Sharmba Mitchell and Zab Judah vaulted him to the top of virtually every pound-for-pound list. The Judah win earned him the IBF welterweight title and “Money’s” legacy would have been much better served had he met long-reigning WBO beltholder Margarito on November 4, 2006 instead of WBC counterpart Carlos Baldomir. Margarito was enjoying the best form of his career as he nearly tore the ear off the head of Sebastian Lujan (KO 10) and knocked out Kermit Cintron (KO 5) and Manuel Gomez (KO 1). The Gomez fight was nine months earlier, so Margarito was more than available to meet Mayweather.
Why this fight made the list: At the time this was the fight to make at 147. The undefeated Mayweather was riding high and, had he chosen to, he was poised to make a historic run through a gauntlet of attractive, legacy-making opponents. Of all the “what-if” fights cited by Mayweather’s critics – Cotto and an undefeated Ricky Hatton at 140, Paul Williams and Pacquiao at 147, among others – the argument against Mayweather’s ultimate place in history begins with why he turned down a then-career high purse to face the most formidable version of Margarito.
What might have happened: Those who recall Mayweather’s troubles in the first Jose Luis Castillo fight would have been anxious to see how the “Pretty Boy” would fare against a super-sized version of “El Temible.” The 5-foot-11 Margarito’s three-inch height advantage, supernatural punch volume and enormous strength at 147 presented a level of danger that would have had the Mayweather-haters salivating. But by the end of the night, they’d have been bitterly disappointed. Mayweather’s superb physical gifts combined with his extraordinary boxing IQ would have dissected Margarito, especially in the late rounds. Mayweather had a way of rising to the biggest occasions and he probably would do it again here. Mayweather by decision.
Honorable mentions: Pernell Whitaker vs. Ike Quartey, Felix Trinidad vs. Ike Quartey, Sugar Ray Leonard vs. Pipino Cuevas, Marlon Starling vs. Simon Brown II, Carlos Palomino vs. Pipino Cuevas