Mayweather and Pacquiao Vs. The Greatest of the Last 30 Years

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COMMENTARY | Floyd Mayweather and Manny Pacquiao are this generation's best welterweights and, like it or not, they will forever be linked together. Whether they ever actually fight one another, and despite Pacquiao's recent knockout loss, this is the era of Mayweather AND Pacquiao.

But how would this generation's best welterweights fare against the best welterweights in recent history?

Here's a look at how both superstars would've handled themselves against some of the best 147-pounders of the last thirty years:

vs. Sugar Ray Leonard

Mayweather: How would Mayweather handle himself against someone just as quick, just as well-schooled, but more offense-minded? It would likely be a long night for Mayweather. He would have too little firepower to keep Sugar Ray from scoring and his in-ring tricks would only allow him to tread water. Winner: Sugar Ray Leonard, Unanimous Decision, 116-112.

Pacquiao: Pacquiao's speed and frenetic energy would mean relatively little to a fighter with the reflexes and overall pedigree of Sugar Ray. It wouldn't be a blow-out, but it's hard to imagine any scenario in which Pacquiao could win. Leonard would figure out the Filipino icon by mid-fight and then start grinding him down. Winner: Sugar Ray Leonard, TKO 12.

vs. Thomas Hearns

Mayweather: Floyd's defense will keep him in the game, but the "Hitman" can also box and would keep the fight even enough through the first half while picking up steam as the fight progresses. Mayweather doesn't have the firepower or the mindset to handle the long and lean Hearns, man to man, in rounds 7-12 of an otherwise even contest. Winner: Thomas Hearns, Unanimous Decision, 117-111.

Pacquiao: Remember Hearns' famous faceplant knockout of Roberto Duran? Expect the same at some point against a hard-charging Pacquiao. If Manny is the usual Manny, expect a most brutal knockout. Winner: Thomas Hearns, KO 5.

vs. Roberto Duran

Mayweather: As good as Duran was, it's hard to forget his "No Mas" performance against a Sugar Ray Leonard who decided to box and use movement in their high-profile rematch. Mayweather could possibly do the same, but it wouldn't be easy. Key to this match-up would be a sharp, focused Mayweather not on his recent once-a-year fight schedule. Winner: Floyd Mayweather, Split Decision, 115-113.

Pacquiao: It would be the war of all wars pitting two tireless, all-offense powerhouses against one another. Duran is a better technical boxer than Pacquiao, but Pacquiao would have the edge in speed. It comes down to execution in this one as both fighters could come away with a win. Winner: Draw

vs. Pernell Whitaker

Mayweather: For the first time in his career, Floyd would be meeting someone even more defensively talented than him. Hardcore fans would be amazed at the tactical and technical prowess displayed here. Casual fans might be be bored silly. At the end of the day, though, Whitaker was a slightly better all-around offensive fighter and that might win the bout for him. Winner: Pernell Whitaker, Split Decision, 115-113.

Pacquiao: Manny would have no idea what to do with someone like "Sweet Pea," whose every movement would throw him off balance and confuse any game plan he'd try to bring into the contest. The bout would be ugly, frustrating, and ultimately one-sided. Winner: Pernell Whitaker, Unanimous Decision, 118-110.

vs. Julio Cesar Chavez

Mayweather: Pernell Whitaker gave Chavez fits with smart movement and offense-stifling defense. Mayweather certainly has the ability to do the same. Chavez, as good as he was, was simply too slow-footed to deal with a true slickster. Winner: Floyd Mayweather, Unanimous Decision, 116-112.

Pacquiao: In a toe-to-toe battle, Chavez would eventually grind down and possibly stop Pacquiao. However, Pacquiao won't be careless enough to go toe-to-toe. He will dart in and out, coming at Chavez from odd, uncomfortable angles. The Mexican would do well in up-close exchanges, but there would likely be too few to really do enough damage. Winner: Manny Pacquiao, Unanimous Decision, 117-111.

vs. Oscar De la Hoya

Mayweather: The tricky part of this pairing is to not draw comparisons between this fantasy match-up and their actual meeting at junior middleweight in 2007. Instead, think of the prime, undefeated De la Hoya from 1999. Oscar was sharp, well-schooled, and strong. He would give Mayweather a much tougher bout than he did eight years later. At the same time, Mayweather would have to absolutely be razor-sharp for this bout. Winner: Floyd Mayweather, Split Decision, 115-113.

Pacquiao: The De la Hoya that Pacquiao stopped in 2008 was severely weight-drained and a mere shadow of his former self. Still, the one-sided romp may have given an insight into a possible stylistic blind spot De la Hoya may have with Pacquiao. Oscar's straight head stylistic orthodoxy could cost him against Pacquiao's unpredictable offensive surges. It would be a lot closer than their 2008 bout, but Pacquiao should still have what it takes to get the win. Winner: Manny Pacquiao, Unanimous Decision, 115-113.

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Paul Magno was a licensed official in the state of Michoacan, Mexico and a close follower of the sport for more than thirty years. His work can also be found on Fox Sports and as Editor-in-Chief of The Boxing Tribune. In the past, Paul has done work for Inside Fights, The Queensberry Rules and Eastside Boxing. For breaking news, additional analysis, and assorted crazy commentary, follow him on Facebook, @TheBoxingTribune or on Twitter, @BoxingBTBC.

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