Floyd Mayweather Jr.’s Five Toughest Opponents

You can make the argument that Floyd Mayweather Jr. is the greatest boxer who ever lived. It’s understandably an absurd argument, since he would be pitted against the likes of Muhammad Ali, Sugar Ray Robinson, Joe Frazier, Jack Dempsey, and Rocky Marciano, just to name a few, who have cemented their place in history throughout vastly different eras in the sport. Some may be hesitant to label “Pretty Boy Floyd” as the greatest combatant to ever live; yet it can’t be denied he’s been the mecca of boxing for several years.

The welterweight’s exceptional record of 45-0, including eight major world titles to his name, is among the best in the sport at the moment. In a world full of padded records and shady business practices to create fights, “Money” has been accused of handpicking his opponents and settling for the easiest payday possible.

He fights Marcos Maidana this Saturday night, May 3rd at the MGM Grand Hotel & Casino in Las Vegas, Nevada for the WBA, WBC and The Ring Welterweight titles.

Mayweather had some tough, gritty opponents in his career. He’s the king of pay-per-views today, yet he had to get there somehow. Mayweather may have not been interested in the Manny Pacquaio fight, although he’s taken the next best opponents out there (minus boxers like Robert Guerrero or Victor Ortiz, who were basically put in the ring to serve as punching bags). We may mistake these opponents as unworthy because Mayweather is so accomplished -- it doesn’t mean because he beats them into a bloody pulp, that they were squash matches for him.

With that being said, here are five opponents who gave Mayweather a run for his money, even though he would have made nearly 10 times as much as they did before the fight even commenced:

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5 Shane Mosley (2010)

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Truth be told, Shane Mosley wasn’t a very difficult opponent for the Michigan-born fighter as the fight progressed. However, the beginning of the bout was a much different story.

Mosley came into this fight as the number three pound-for-pound boxer on the planet according to Ring Magazine, putting his WBA super-welterweight title on the line. What Mosley had at the time was power, something Mayweather’s previous opponents weren’t necessarily known for. “Sugar” was a stiff test for the challenger, capable of getting the job done. In terms of Mayweather’s previous opponents, his chances were better than anyone’s.

The fight began fairly even, with Mayweather looking slightly off his game. The shot heard around the world came in the second round, when “Sugar” decked “Money” with a left hook square on the jaw and fans packing in the MGM Grand Hotel & Casino began to erupt. Mosley had stunned Mayweather, but failed to capitalize on his blow.

After the second round, Mayweather broke down the older fighter en route to an extremely easy decision win.

4 Miguel Cotto (2012)

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By the time Mayweather met Miguel Cotto, the pride of Michigan was already touted as unbeatable. There was a chance for Cotto to stun Mayweather, but was the Puerto Rican able to match up with Mayweather’s speed and technique?

The first few rounds commenced like familiar Mayweather fights in the past. His opponent would try to throw everything but the kitchen sink at him, yet the talented welterweight would bob and weave his way out of danger, dishing out stinging counterattacks wherever he saw fit.

It was something we already knew, but Cotto had to make things incredibly scrappy if he wanted any chance of victory. He basically had to go out on his shield. Even if the underdog had no chance of winning, the least he could have done was make it an entertaining fight.

That’s exactly what he did.

In the later rounds, Cotto would have Floyd up against the ropes, and although “Money” did his best to stay out of Cotto’s range, the Puerto Rican hit him with a few good shots to gain some advantage. He hit Floyd several times square on the chin and the crowd started buzzing. It may have won him a few rounds, but ultimately, the result was already determined.

It would be another win for Mayweather over one of his most durable and toughest opponents yet, claiming the WBA Super Light Middleweight title -- showing that he can compete while being a few pounds heavier.

3 Jose Luis Castillo (2002)

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This is arguably Mayweather’s closest decision win of his career -- or a robbery, depending who you ask.

Many pundits felt like Jose Luis Castillo should have won this bout. Coming in at the tender age of 25 years old, “Money” looked superb in the opening sequences, before being cut above his left eye. He also threw a punch in the second round, which didn’t connect with Castillo’s face properly, but the Mexican went down and it was ruled a slip.

The fight looked to be dead even midway through, with Castillo turning up the intensity. Mayweather was getting hit more times than he had in his professional career and Castillo wasn’t tiring. The Mexican went to the body often too, and it was a great way to wear down his opponent.

A big moment in the fight was when Castillo was deducted a point for punching Mayweather after the referee’s break, after being warned. A point was taken away from “Money” shortly after for an elbow.

In the 10th round, the fight looked like it was for the taking, and the last two rounds were questionable, since Castillo pressed on while Mayweather counterstruck. The punch stats had Castillo ahead in every category.

In the end, Mayweather was given the controversial decision and beat Castillo in the rematch directly after.

2 Saul Alvarez (2014)

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The brightest future in boxing belongs to Saul Alvarez. At the tender age of 23 years old, “Canelo” has already held two major titles, including victories over notable fighters like Shane Mosley, Austin Trout, Kermit Cintron and Carlos Baldomir. He’s also fought Mayweather, who delivered him his only loss in his entire 45-fight career thus far.

The Mexican had a good chance of success in his September 2013 fight against Mayweather, even though he was an underdog. Plenty of publications liked Alvarez’s chances, however, what could he have brought to the table that Mayweather hadn’t seen before?

Alvarez’s speed would be the deciding factor. He had good hands, capable of knocking opponents out, but he had to be lightening-quick if he wanted to dethrone the king (even though he came into this fight as the champion).

“Canelo” didn’t look like the faster fighter when he finally met Mayweather in the ring, as “Pretty Boy” schooled him in almost every aspect of the fight. There were some rounds won by “Canelo,” but he was simply hyped up to be something he wasn’t.

1 Oscar De La Hoya (2007)

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This fight was deemed as one of the biggest fight in boxing history. You had the Ali vs. Frazier trilogy, along with Ali’s bouts against George Foreman, and you could say Mike Tyson vs. Evander Holyfield 2 was as mainstream as the sport would get. This was your welterweight version of all those fights combined. It did roughly 2.4 million pay-per-view buys, becoming the biggest boxing pay-per-view in the history of the sport.

Many believed Oscar De La Hoya was able to do the job. He was past his prime, and already on the downside of his career, yet there was still hope. Had Mayweather challenged an earlier version of De La Hoya, who knows what could have happened? Also, it must be noted that Floyd Mayweather Sr. was De La Hoya’s trainer since 2001, but they couldn’t reach an agreement for this fight, so De La Hoya hired Freddie Roach.

In the beginning of the fight, “Money” was having his way with the slower De La Hoya, beating him to the punch and lacing him with slicker combinations. De La Hoya couldn’t connect and therefore looked like he was chasing Mayweather around the ring. He did throw a lot of punches, but the percentage wasn’t even close to what Mayweather was throwing and landing.

Still, De La Hoya’s willingness to keep moving forward exhausted him and he was willing to take the risks. Mayweather’s hand speed was a notch above his, but the fight really proved to be a classic, with De La Hoya doing better in the second half of the fight.

In the end, Mayweather won the decision, and even though some pundits felt otherwise, it was the right call.

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