Ranking the Toughest Fights of Floyd Mayweather's Career

Briggs Seekins@BriggsfighttalkFeatured ColumnistSeptember 11, 2014

Ranking the Toughest Fights of Floyd Mayweather's Career

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    Ethan Miller/Getty Images

    Saturday night in Las Vegas, Floyd Mayweather fights his first rematch in more than a decade when he faces Marcos Maidana. The tough Argentine made their initial meeting last May a wild ride, giving Mayweather his toughest fight in years. 

    Mayweather came away with a majority decision, but Maidana made it clear that he thought he should have won. A certain percentage of fans agreed with him. 

    With no other obvious opponent available, a rematch made sense. Mayweather wants to remove any doubt over his dominance, and Maidana wants to take what he believes he earned the last time out. 

    It's been a rarity over the years when Mayweather has had a hard night of work. Boxing is never an easy sport, but Mayweather comes very close to making it look like it is at times. 

    These fights have been the toughest of his career. 

8. Shane Mosley, May 1, 2010

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    On the cards, this fight between future Hall of Famers Shane Mosley and Floyd Mayweather was hardly close. But I don't think it's a stretch to call it a tough fight.

    In Round 2, Mosley caught up to Mayweather with a blistering shot that had the pound-for-pound king badly buzzed and hanging on in survival mode. It's an incident that should dispel any speculation that Mayweather doesn't have solid whiskers.

    Mayweather reasserted control of the fight in the next round and was never seriously threatened the rest of the way. But getting hit flush in the face is never easy, especially when the punch is coming from a multi-division champion.

7. Zab Judah, April 8, 2006

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    For a time in the middle part of the last decade, this was the most anticipated fight in the sport. Zab Judah and Floyd Mayweather appeared to be cut from the same cloth. Both men were brash, cocky young champions with dazzling speed and excellent technical skill.

    When Judah went down by shocking upset to Carlos Baldomir in early 2006, at first it looked like this major event would be scrapped. In the end, the fight still took place, though it was a significantly smaller payday for both men.

    Judah started strongly in this fight and gave Mayweather fits in the early going. Judah could nearly match Mayweather's speed, and his southpaw stance presented a puzzle.

    But as the fight went on, Mayweather made adjustments and took firm control of the fight. By the end of the night, it was clear that the two were on different levels.

    This fight is memorable above all else for the in-ring brawl that broke out in Round 10 following a low blow by Judah.

6. Miguel Cotto, May 5, 2012

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    Now that Miguel Cotto has captured the lineal middleweight title with his sensational defeat of Sergio Martinez last June, I wouldn't be surprised to see a rematch take place. I think Cotto believes he could do better than he did last time, and I am sure Floyd Mayweather would like to burnish his record with a world title at middleweight.

    Their fight in May 2012 ultimately wasn't that close. Cotto won no more than three rounds on a single card, and I can see no argument for giving him more than four at the most.

    Still, the Puerto Rican star made the pound-for-pound king work hard in every round. Cotto applied consistent pressure, committed to his body attack and even managed to bloody Mayweather's nose.

    It was a clear win for Mayweather, but it hardly looked easy.  

5. Emanuel Augustus, October 21, 2000

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    Emanuel Augustus is a classic case of a journeyman fighter who might easily have been a contender if his career had been handled a little bit differently. He turned in a 38-34-6 record for his career with 20 KOs. But that record hardly tells the story.

    I wouldn't even want to guess how many times Augustus got the tough end of a close decision. But in July 2004 he suffered what I would rank as the worst judging decision of this century when he "lost" by split decision to Courtney Burton in Burton's hometown.

    Nicknamed "The Drunken Master," Augustus was a tricky, unorthodox fighter with a highly entertaining style. He could also hit with some power.

    Floyd Mayweather was coming off from a nine-month break when he faced Augustus, who was then known by his birth name of Emanuel Burton, in October 2000. The boxing protege ended up getting the fight of his young life before winning by TKO in Round 9.

    I think Mayweather is overstating the case for Augustus as his toughest fight in the clip included here. But there's no doubt the tough journeyman forced him to dig deep. And I can appreciate the desire to heap some praise on an unsung legend like The Drunken Master.

4. Oscar De La Hoya, May 5, 2007

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    Floyd Mayweather only won this fight by split decision, but I can't imagine what Tom Kaczmarek was watching to have scored that fight 115-113 for Oscar De La Hoya. I was with Chuck Giampa at 116-112.

    But De La Hoya did do a very good job of applying pressure in the first part of the fight. Mayweather was forced to hustle hard against a bigger, extremely skilled opponent. Only in the last part of the fight did he really pull away and make things look decisive.

    This fight was a turning-point fight for Mayweather as an all-around star. It broke records for pay-per-view sales and marked the emergence of Mayweather's "heel" persona, as he switched from "Pretty Boy" to "Money."

3. Jose Luis Castillo II, December 7, 2002

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    Ethan Miller/Getty Images

    More than a decade ago, this fight was the last rematch Floyd Mayweather fought. It's the last time there was any need for him to fight an opponent a second time.

    Eight months prior to this, Jose Luis Castillo dropped a unanimous decision to Mayweather that many observers felt he deserved to win. The HBO broadcast team all had the fight for Castillo.

    In this rematch, the tough, pressure fighter Castillo once more gave Mayweather almost all he could handle. Once again, it was a very close fight. In this fight, though, I think Mayweather clearly won.

2. Marcos Maidana, May 3, 2014

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    Like many, I thought this fight seemed a bit less close the second time I watched it. Live, I thought Mayweather had won but wasn't sure if Maidana's activity level might earn him the nod. 

    On second viewing, it became even clearer to me that Maidana was missing with a high percentage of his punches. 

    The thing is, fights are not scored with the benefit of a second viewing. So Maidana deserves a lot of credit for the way he created such a frenetic pace, earning himself a draw on one card and enough supporters to gain a second chance this weekend. 

    I think Mayweather will continue to make the same mid-fight adjustments he made in the first bout and win an even clearer decision this time around. But like so many, I never saw such a competitive fight coming in the first place. 

    No matter how many rounds a fan might have given Mayweather last May, it can't be denied that Maidana succeeded in forcing the pound-for-pound king into a very tough fight. 

1. Jose Luis Castillo I, April 20, 2002

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    This fight remains the most controversial of Floyd Mayweather's career. More than a decade after it took place, fans still argue on Internet forums that Jose Luis Castillo deserved the nod over Mayweather in April 2002. 

    On paper, the argument in favor of Castillo is persuasive. He threw more punches and landed at a higher percentage. As noted by the Boxrec entry on this fight, HBO's unofficial scorer, Harold Lederman, had the fight 115-111 for Castillo. 

    I feel it was a close fight and that the margins by which the judges gave the fight to Mayweather contributed to the outrage. But I've linked the entire fight here so readers can judge for themselves. 

    Fighting with an injured shoulder, Mayweather was lucky to escape undefeated. To this point, it remains the toughest fight of his career. 


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