Boxing legends Oscar De La Hoya and Floyd Mayweather Jr. remain two of the most iconic figures in the sport, with their 2007 showdown marking one of the most memorable events in boxing history. Recently, De La Hoya opened up about that fight, suggesting that a few different choices on his part could have led to a vastly different outcome—potentially even a knockout victory over Mayweather.

During a recent appearance on the Club Shay Shay podcast with Shannon Sharpe, De La Hoya made some bold claims about the fight, which ended in a split decision victory for Mayweather. When asked if having Mayweather Sr. in his corner might have changed the result, De La Hoya responded confidently, "Knock him out. I would've knocked him out. Really."

He elaborated further, stating, "If I was one year younger and had Sr. in my corner, I would've knocked him out. Absolutely." De La Hoya, who was known for his powerful jab, admitted that his failure to maintain that key aspect of his strategy was crucial to his defeat. "The key to that style, the Philly Shell, is a jab. It opens up all the doors," he explained. Reflecting on his performance, he acknowledged, "When my jab failed me, it was over. I knew it in my heart, in my head."

Beyond the tactical aspects of the fight, De La Hoya also revealed that he had considered hiring Mayweather Sr. as his trainer for a potential rematch but ultimately decided against it. "He wanted too much money," De La Hoya disclosed, adding that he also felt it would have been morally wrong, considering the strained relationship between Mayweather Sr. and his son at the time. "I said, 'No, I can't do this. I cannot do this to a family who has been in the business for a very long time.'"

The relationship between Mayweather Sr. and his son was fraught with tension, including a notable public fallout in 2000. Despite this, De La Hoya chose not to pursue Mayweather Sr. as a trainer, in part to avoid deepening the rift between father and son. "Aside from [money], morally, I think it was wrong," De La Hoya remarked.

While De La Hoya's reflections invite speculation about what might have been, the fact remains that Mayweather retired in 2017 with an impeccable 50-0 record, solidifying his place among the sport's greatest. However, De La Hoya remains proud of his performance, noting, "I fought against the best Floyd Mayweather, in his prime, you know, undefeated... So I was pretty proud [of] what I accomplished that night."

The mutual dislike between two of the best fighters of the last generation — Floyd Mayweather Jr. and Oscar De La Hoya — not only existed ahead of their 2007 super fight but continued on well afterward. Even though Mayweather went on to fight many times under De La Hoya’s Golden Boy Promotions banner, it is often said that Mayweather did so because of his relationship with Richard Schaefer, who was the company’s CEO at the time. When Schaefer and Golden Boy split, Mayweather ended his relationship with Golden Boy as well (as did a number of other fighters).

Over the years, De La Hoya hasn’t been shy about trashing Mayweather. He’s also complimented Mayweather on occasion, too. But it was nonetheless a little surprising, and also rather refreshing, to hear De La Hoya praise Mayweather while speaking with Hall of Fame football player Shannon Sharpe in a recent episode of Club Shay Shay. "Floyd is a great fighter," De La Hoya said. Later, he called Mayweather "one of the best."

"I love his patience," De La Hoya said. "I love the fact that he’s a hard-hitter and he has a chin. People discredit him for not having a chin. He has a chin. And he has a big heart. What makes him unique is obviously his boxing ability, but his ring generalship is what does it for me. He knows how to pick his spots. He knows how to get you tired without even throwing punches. It’s crazy."

Mayweather topped De La Hoya by split decision all those years ago. De La Hoya believed at that time that he had done enough to win. "When you’re a fighter inside the ring, when that final bell rings, you know it in your heart, in your gut and physically if you won or you lost. You just feel it. It’s a sensation, and I just felt it," De La Hoya said. "Whether I was wrong or I’m right, I don’t care. It doesn't matter. I fought against the very best in Floyd Mayweather, younger, in his prime, undefeated. And I was over the hill, tons of injuries. I was pretty proud with what I accomplished that night, so maybe I was convincing myself that I won, but I did feel it physically and mentally that I did enough, because I was the champion in that fight.

"You take all those variables. I felt maybe I [convinced] myself that I won that fight," De La Hoya added. "It’s a 12-round fight. As an elite fighter, you’re always keeping track of what you’re doing every second, every minute: ‘OK, I have this round in the bag, I have this one, this one, OK, that's maybe six or seven. Let me cruise.’ If I get injuries just the way I did during the fight, because I had torn rotator cuffs going into the fight, you start thinking, ‘If I just cruise here and land a few punches, I got the first half won already, so maybe if I just win one more round, I can win the fight 7-5, maybe a draw.’ You start thinking that, and that can be a mistake, or it can be a plus. Obviously that night for me it was a big mistake. I should’ve just gone out there and given it my all."

De La Hoya’s respect for Floyd Mayweather Sr.—Is tough love the best way to train champions?

Oscar De La Hoya holds boxing legend Floyd Mayweather‘s father, Floyd Mayweather Sr, in high regard. So much so that he wanted to avail his services to defeat his son at the event billed ‘The World Awaits’ on May 5, 2007, at the MGM Grand Arena in Las Vegas. However, the steep price of $2 million demanded by Mayweather Senior was too much for the 1992 gold medalist, and he hired Freddie Roach instead. For the unversed, ‘Golden Boy’ was trained by Mayweather Sr. from 2001 through 2006.

In a recent interview with sports analyst and former NFL tight end Shannon Sharpe on his podcast Club Shay Shay, De La Hoya revealed that his world champion and Gold medalist Olympian status couldn’t help him get any special treatment from Mayweather Senior. The legendary boxing trainer made sure that De La Hoya never went out of line under his stewardship.

Putting on the airs of a world champion boxer wouldn’t float with Floyd Mayweather Sr. And, De La Hoya learned it the hard way. One of the reasons why 50-0 boxer Floyd Mayweather turned out to be an elite champion is because he was very disciplined, which Oscar believes he learned from his father.

Talking to Sharpe about the Mayweather family mindset, De La Hoya explained, “His father had something very unique, he was a sergeant. I think Floyd has that same attribute where it’s like he takes no [ __ ] from nobody you know.” Thereafter, De La Hoya remembered the incident that made him admire Mayweather Senior.

“I remember one time his [Floyd Mayweather’s] father dumped a water bucket on me at 5:00 a.m. in the morning to wake me up to go run,” Oscar reminisced, pointing out that for Floyd Mayweather senior the usual routine of a boxer doesn’t change depending on star power. “Nobody has ever done that, not to The Golden Boy, come on… and he did it and I respected him from that day on.” the boxer-turned-promoter respectfully remarked about Mayweather Sr.

What’s more? De La Hoya still believes that if the legendary trainer was in his corner during his fight against Floyd Mayweather, he would have defeated him.

De La Hoya seemed fairly sure about the fact that he could have not only defeated but “knocked out” Floyd Mayweather if he was trained by Floyd Sr. "If I was one year younger and had Sr. in my corner, I would knock him out. Really," the Olympian told Shannon Sharpe confidently. Furthermore, Oscar stated that later in his professional career he figured out how to bypass Floyd’s Philly shell. He claimed that the “key to the style” is the jab.

However, he revealed to Sharpe that by the time there were talks about a rematch with Floyd, his jabs “failed”  him.”I knew it in my heart, in my head. I knew it was over,” the Olympic Gold medalist former boxer revealed.