Two of the finest boxers from two different generations are often the subject of debate when it comes to theorizing just who would come through between Floyd Mayweather Jr and Ray Leonard had they squared off to decide supremacy.
A former gold medalist, Leonard was the media darling for the majority of the 1980s. He won his first world title in 1979 with a 15th round TKO win over Wilfred Benitez. He showed tremendous footwork, hand speed, great punch resistance, blistering combinations and the ability to both box and fight when needed to. He made one successful title defense against Dave Green before running into Roberto Duran, who is widely considered to be the best ever lightweight to have put on a pair of gloves, in June of 1980. The build up was full of drama, with insults being directed at Leonard’s wife from the vicious Panamian. This seemed to have worked for the challenger because Leonard made the decision to stand and trade for much of the 15 round bout, as if he wanted to prove something to his famous adversary and possibly to himself. But this tactic caused him to face the first ever loss of his career when he saw a unanimous decision go against him.
Five months later the pair cemented their rivalry, and years later a trilogy, with a return bout. But this time it was a whole different ball game as Duran was bewildered by the movement, fast defensive reflexes, smart counter punching and ring IQ of Leonard who made him quit during the 8th round. It was a choice that would go on to be known as the “No Mas fight” despite the fact that Duran never actually uttered those words. Their “rubber” match in 1989 was a lifeless affair compared to their first two clashes which ended in a split decision win for Leonard. Duran would go on to admit that he only took this fight because he owed taxes to the IRS.
The following year in 1981, Leonard would already be participating in his fourth classic encounter when he faced Tennesee’s Thomas Hearns. Behind on all three judges score cards, it was Leonard’s turn to inflict the first defeat of a future legend when he sent Hearns through the ropes during the 13th round. The bell saved him, but it was inevitably a win for Ray at this point when he came out for the 14th to rain down blows which forced the referee to step in. As with the third Duran fight, which also took place in 1989, it failed to ignite much excitement with the exception of rounds 3 and 11 when Leonard was knocked down during both. A draw was declared.
Perhaps the most controversial contest of “Sugar Ray’s” resume occurred in 1987 when he faced middleweight legend, Marvin Hagler. To this day, opinions are divided on who really should have won the fight. Leonard used his mobility and fast flurries on a pursuing Hagler, who landed the heavier blows. A split decision went against “Marvelous,” leaving him so distraught that he completely walked away from boxing soon after.
But it was after the third Duran bout that saw Leonard’s physical attributes decline to a great degree. When he tried to make a comeback in 1991 against Terry Norris his record took it’s second loss. Another retirement followed only for Leonard to try to defy time once more in March of 1997 when he was knocked out in the 5th round by Hector Camacho. The five weight former champion would never fight again.
Unlike “Sugar” Ray Leonard, however, Floyd Mayweather Jr spent the majority of his career struggling to gain popularity. Making his debut in 1996, he too, would finish his career as a five weight champion with the WBC belt being the one that he valued the most. He retired Genaro Hernandez in 8 rounds in 1998 to win the WBC super-featherweight title and beat some good talent in Angel Manfredy and Diego Corrales, who was seen as his most dangerous test at the time. His first match with Jose Luis Castillo caused a stir when it was widely seen as a win for the Mexican, however, Mayweather’s hand was raised. Then known as “Pretty Boy Floyd,” Mayweather settled unfinished business when he gave Castillo a rematch in December, 2002. This time Castillo was soundly outboxed and any doubts that existed about Floyd’s ability to overcome him were wiped out.
Floyd’s time at light-welterweight was pretty forgettable with the exception of a one sided beating of Arturo Gatti in June, 2005 although he did win his third WBC crown. Wins over Zab Judah and Carlos Baldomir saw him win his fourth strap but he was still failing to make the public appreciate his supreme ring generalship, defensiveness and the amazing ability to adjust tactics when necessary. However, all of this would change when he got the fight he had wanted for years – a mega money match with Oscar De La Hoya in May, 2007 for the 154lb WBC title.
With an image change and now going by the handle of “Money,” his new promotional persona was designed to entice the fans to take interest by often showing off his materialistic assets and throwing dollar bills out to anyone who was around him in order to provoke a feeling of resentment. This seemed to work as people would tune in and hope they would see him lose. The fight was a huge success with Floyd winning by a split decision. Another hugely successful fight with Britain’s Ricky Hatton at 147lb saw Mayweather walk away from the fight game until 2009 when he returned against Mexico’s Juan Manuel Marquez.
It was at this point that the fights the fans had always wanted to see Mayweather take part in were finally happening. Shane Mosley, Miguel Cotto and Saul Alvarez all tried and failed. Then a long awaited duel with Manny Pacquiao took place in May, 2015. The battle was a clear win for Mayweather on points and he earned $240,000,000 for thirty six minutes of work. Two more ring returns against Andre Berto and UFC star, Conor McGregor raised Floyd’s win statistic to a nice and round 50-0. As of writing here in 2019, this number remains unchanged.
It is clear to see why, had both boxers campaigned during the same era, a fight between Leonard and Mayweather would have been a huge event! There wasn’t much that Ray could not do. On the other hand, Floyd’s talent for hitting and not being hit in return was an ability that no other boxer really has possessed. The confrontation would likely have taken place over 12 rounds at 147lb where both boxers fought their most notable engagements.
The pair of them were great counter punchers and I can see Ray taking a more technical approach to this fight. He would attempt to wait for Floyd to throw and then make him pay for his mistakes. But the problem for him would be that Floyd would also adopt this same tactic! He would try to land the cleaner blows. With the fight playing out like a chess match, it would be one the purist would most likely appreciate. There is a chance that Leonard would step on the gas during the last four rounds. But if he didn’t then both boxers would be trying to outwit the other to the final bell. Floyd was good at controlling the tempo of a fight and he would do a decent job of that here.
If Leonard pressed the action toward the end then Floyd would likely keep his composure, score the more eye catching counter punches and he would win by a split decision. If the fight remained at the same pace and failed to catch fire then Leonard would snatch it, also by a split decision.