50 fights, 50 wins: that’s the Floyd Mayweather Jr. story in a nutshell. But that isn’t to say he wasn’t challenged, including well before his final professional appearance in a boxing ring in 2017. José Luis Castillo, way back in 2002, was the first fighter to truly put Mayweather to the test.

Always a defensive fighter, it wasn’t particularly surprising to see Mayweather leave it to Castillo to control the pace of the bout. Starting in the middle rounds, though, it looked more like Mayweather was getting downright cornered, with body blows landing in large numbers. Here’s how Castillo became the first boxer to truly challenge Mayweather’s scorecard-focused undefeated style.

Expectations going into Castillo vs. Mayweather I

Castillo vs. Mayweather I was to be Mayweather’s first test at the lightweight level. He tore through every junior lightweight fight put before him, but this next step was something of a mystery. His win was not a foregone conclusion. Castillo was the first gatekeeper of a new tier.

Castillo held the WBC lightweight belt at the time. He got there by taking down previous champ Stevie Johnston in a tight bout. The fight was essentially inconclusive, until a final round explosion gave the underdog Castillo enough of an edge to earn a unanimous decision.

Johnston exercised his option to re-match, and it was another close fight through the fourth. Castillo knocked him down twice in the final rounds, though, enough to hold onto the belt. That made Castillo the main target for the dominant junior lightweight Mayweather, who was the immediate favorite in the coming match.

How Castillo executed upon a strong blueprint to defeat Floyd Mayweather

Despite just entering a new weight class, Mayweather immediately earned a shot at Castillo’s title off the strength of his incredible 27-0 record. Much of that run was similar to the version of Mayweather most are familiar with now that he’s retired. He displayed impeccable defense, used energy on body blows at a perfect rate to stay ahead on the scorecard, and went in for K.O. attempts as a late-round gambit.

Castillo and his corner took this in and executed their counter-strategy accordingly. In the early rounds, he was still taken off guard by Mayweather’s seemingly superhuman ability to avoid blows. That changed in the middle rounds, as Castillo figured out how to force Mayweather backward, rather than dodging and countering. Usually, Mayweather controlled the pace of his fights from start to finish. Not this time.

This pace continued to the very end of the fight. Castillo walked Mayweather down, landed blows, avoided counters. He thought he had the fight in the bag. “Oh, no doubt, after 12 rounds I thought I had done more than enough, certainly more than he did,” Castillo told Sports On Earth over a decade later. “But they didn’t give me the decision.”

Why did the judges score Floyd Mayweather so well?

The general pace of this fight, especially for the final half, seems to be in Castillo’s favor. That’s how this bout ended up as the most enduring and infamous fight of Mayweather’s career, even after a rematch later in 2002 more clearly went Mayweather’s way.

The tone of the commentators on the original HBO broadcast also contributes to the feeling that, perhaps, Mayweather deserved to take his first and only loss in this bout.

The round-by-round details, as broken down by Bad Left Hook, illuminate why this wasn’t the case. Castillo looked as lost as Mayweather’s previous 27 professional opponents in the early rounds. He took a bloody nose right of the bat, in the very first round. Mayweather’s quick right hand clearly does damage.

Mayweather’s left doesn’t seem to go anywhere by the middle rounds. He adjusts, leans more on his devastating right even as Castillo walks him down. And the back half might not be as dominant as popular perceptions hold.

Castillo takes big damage from Mayweather’s right hook, including in rounds the judges ultimately gave to Castillo. Once it wraps up, perhaps there is a case to made that it was close. But overall, Mayweather never breaks. He lands the biggest hits, rare though they were. It was Mayweather’s worst fight, but still an earned win.



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