Timeline of Floyd Mayweather's Feud with Oscar De La Hoya

Kevin McRaeFeatured ColumnistSeptember 10, 2013

Business partners? Check. Friends? Not so much.
Business partners? Check. Friends? Not so much.Ethan Miller/Getty Images

Pound-for-pound king Floyd Mayweather will meet Saul "Canelo" Alvarez for the junior middleweight championship on Sept. 14 in a bout many feel could challenge the holy grail of boxing revenue records—pay-per-view buys.

To do so, Mayweather vs. Canelo will need to surpass the approximately the 2.4 million buys that Floyd and longtime rival/business partner Oscar De La Hoya secured for their May 5, 2007 bout. That bout sparked a rivalry that lasts to this day.

If they do break the record, they'll do it without De La Hoya, who recently checked himself into a rehab facility and will miss the fight. "The Golden Boy" has had several notable struggles with drugs and alcohol during his career, and this is something Mayweather hasn't been shy about pointing out in the past.

Mayweather and De La Hoya made a ton of money from their fight, and the two have enjoyed an extremely lucrative business relationship ever since. But make no mistake about it, their relationship is often contentious, and the two will never be best friends. 

But boxing is a business, and these two men have done a ton of it together. Rivalry and bitterness can all be set aside in the name of the almighty dollar, but that doesn't mean it isn't an interesting story.

This is that story.



Tale of the Tape

There's no doubt that Oscar De La Hoya and Floyd Mayweather are the two biggest crossover stars in recent boxing history, and they have similar histories, but wildly different personalities. 

Both men represented the United States at the Summer Olympics—De La Hoya captured lightweight gold at the 1992 Barcelona games, while Mayweather was robbed of gold and had to settle for bronze at the 1996 Atlanta games. Both rank amongst the biggest stars in boxing history and both warrant consideration amongst the greatest fighters of all-time, but the contrast in personalities is stark.

De La Hoya made his career, both as a fighter and promoter, by being extremely clean and polished. He rarely engaged in smack talk or was disrespectful of an opponent. He appeared as comfortable in a suit as in boxing trunks, and he had the perfect image for a crossover star who understood how to market himself.

Mayweather, on the other hand, is unapologetic about who and what he is, both inside and outside the boxing ring. He's brash, some would say arrogant, and he's spent much of his career rubbing people the wrong way. But like De La Hoya, he has carefully crafted an image—the sport's top villain—that has allowed him to become not just the sport's top fighter but also its top draw.



2006: Prelude to a Superfight

When it was announced in November of 2006 that Oscar De La Hoya would defend his WBC junior middleweight championship the following May against Floyd Mayweather, you could take your pick of storylines.

De La Hoya, for years boxing's face and premier cash cow, was beginning to wind down his Hall of Fame career. He would be 34 years old on fight night, and he would be taking on a younger, undefeated fighter who was already being mentioned as a potential all-time great.

Mayweather had just captured the welterweight championship, and he would be forced to come to the fight at the highest weight of his career in order to challenge for the 154-pound title. He was the anti-Oscar—brash, outspoken and often times disrespectful—and would enter the ring looking to change the guard.

An added wrinkle in the lead up to the fight revolved around the sometimes soap opera like relationship between Mayweather and his father Floyd Sr. 

De La Hoya had been trained by the elder Mayweather starting in 2001, and there was some question whether or not he would be able and willing to train "The Golden Boy" to fight and ultimately beat his son.

Negotiations between De La Hoya and Floyd Sr. quickly fell apart, and ESPN's Dan Rafael later reported that it was over money and not family ties.

Freddie Roach would ultimately get the assignment when Mayweather Sr. turned down De La Hoya's financial terms.



2007: 24/7

WARNING: The above video contains EXPLICIT language.

The unprecedented hype for the De La Hoya vs. Mayweather clash on May 5, 2007 was buoyed by the debut of an original HBO series entitled De La Hoya-Mayweather 24/7.

At the time, it was a groundbreaking look into both fighters training camps, personalities and psyches heading into the biggest fight in the sport. It was so successful, that it has become a consistent feature of every major fight since, with HBO maintaining the 24/7 format and Showtime launching All Access.

The show once again emphasized the differences between the two fighters. 

De La Hoya was mostly reserved, but seemed to often get agitated by Mayweather's over the top antics.

These antics included bringing a chicken in a cage labeled "Golden Girl" to a press conference, stealing De La Hoya's gym bag and calling him virtually every unsavory name in the book and a few not in there.

The trash-talk took on an overly personal tone between the two, and once again emphasized that for whatever part of the show was meant to sell PPV's, there was genuine animosity between the men.

Watch for yourself.



May 5, 2007: The World Awaits

It was called "The World Awaits," and for one night in May of 2007, the focus of the entire sports world was directly on boxing.  It was "The Golden Boy" versus the "Pretty Boy" and it would be remembered as the night all sorts of boxing records were shattered.

Floyd Mayweather entered the arena first, and immediately showed his attempts at getting under De La Hoya's skin wouldn't end on fight night. 

It wasn't enough that he would be donning Mexican flag themed trunks for the fight, but he also wore a sombrero in, perhaps equal parts acknowledgement of his popularity with Mexican fans and as mock homage to his foe's heritage. 


De La Hoya was much less flashy on his way to the ring, and he began the fight well. 

The early rounds were close and competitive. De La Hoya attacked early and often behind his jab, and while Mayweather landed the cleaner punches, the fight was even at the midway point.

But as the fight went on, Mayweather's sharper punches began to carry the day, and as De La Hoya inexplicably abandoned his jab, it was Floyd who landed with greater regularity. 

The decision remains somewhat controversial to this day. You'll find a diversity of opinions—everything from Oscar deserved at worst a draw to Floyd should've won by a more convincing margin—but ultimately it would be Floyd Mayweather who claimed a narrow split-decision by scores of 115-113, 115-113 and 113-115.

One interested, but possibly biased, observer felt the judges got it wrong. Floyd Mayweather Sr. had this to say:

I thought Oscar won the fight on points, threw more punches and was more aggressive. My son had good defense and caught a lot of punches but Oscar pressed enough to win the fight.

Take that for what you will, after all, Floyd was sitting in a $2,000 ringside seat given to him by De La Hoya.


2008: The World Awaits...Again?

The fight was close, and it broke virtually every boxing revenue record known to man. At the time it was the richest live-gate (since surpassed by Mayweather vs. Canelo) and the best selling PPV. It generated the most revenue in boxing history.

Given all that information, a rematch seemed all but a guarantee. And there was a point where it seemed that it was a done deal.

Early in 2008, it was reported by Dan Rafael of ESPN.com that Golden Boy Promotions CEO Richard Schaefer felt a deal for a rematch was close to being finalized. Mayweather had just impressively knocked out the previously undefeated Ricky Hatton, and De La Hoya was scheduled for a May tune-up fight against former champion Steve Forbes.

De La Hoya would go on to easily defeat Forbes, and the rematch was tentatively penciled in for September 20, 2008, but then Mayweather made a shocking announcement.

He was retiring from the sport, and unlike his previous decision to walk away after capturing the welterweight title from Carlos Baldomir in 2006, this one seemed legitimate. 

This involved walking away from untold millions of dollars. This time, he promised the decision was final, and he would never step inside a boxing ring to fight again. 

As for Oscar, he was only one fight from retirement himself. Instead of facing Mayweather, he would face Manny Pacquiao in December 2008, and he would lose the most one-sided fight of his professional career. 

He rightly called it quits shortly after.


2009: The Business of Boxing

Lest we ever forget, boxing is a business. It's about making money.

When Mayweather returned to the ring in 2009—after a 21-month layoff—he resumed his lucrative relationship with Golden Boy Promotions. 

While Floyd technically fights under the Mayweather Promotions banner, the cooperation between the two companies is such that they've become largely synonymous.

All his fights—since his clash with De La Hoya—have been co-promoted, and that includes his upcoming clash with Canelo Alvarez.

It just goes to show you, for all their disagreements and issues over the years, Oscar De La Hoya and Floyd Mayweather are boxing's ultimate dynamic duo.


September 2009-May 2010: 'He Maybe Had No Chance...He Was Done'

On his return, Floyd Mayweather selected Juan Manuel Marquez to be his opponent. 

There was some consternation amongst fans and media, many of whom expressed concerns that Marquez—who had only fought above 130-pounds twice—would be woefully undersized coming up to the 147-pound welterweight division. 

Those concerns proved to be well founded, and it didn't help matters that Mayweather failed to meet the contractual weight limit of 144-pounds for the fight. He was forced to pay Marquez a substantial penalty for coming in two pounds heavy.


Mayweather was visibly bigger, stronger and quicker. He absolutely dominated Marquez, knocking him down in the second round en route to a unanimous decision victory in which you could easily give him every single round.

Mayweather has never received full credit for this victory. It's been largely dismissed due to the weight issues, and that is something that Oscar De La Hoya emphasized during a 2011 interview with The Ring Magazine's Lem Satterfield:

Marquez, yes, you can make the case that he was a small welterweight, which he is. In a lot of people's minds, and, I guess, the reality was that he had maybe no chance.

De La Hoya had something similar to say about "Sugar" Shane Mosley, who would lose to Mayweather in similarly lopsided fashion in his next fight, though in fairness, nobody was saying this before the fight:

In my eyes and my heart, I wanted him to have a chance and I wanted him to have that opportunity. The same goes with a Shane Mosley. In everybody's eyes, realistically, in the eyes of the experts, he was done. He was not the Shane Mosley that I fought when we fought for the first time years earlier.



September 2011: Victor Ortiz and the Punch

By now—if you're a boxing fan—you know the story. 

In the fourth round of their hotly anticipated bout, a clearly frustrated Victor Ortiz bulled Floyd Mayweather into the corner and let his hands go. If were just his hands, there would've been no problem, but Ortiz also uncorked a huge and deliberate headbutt square to Mayweather's chin that forced a stop to the action.

Ortiz immediately went over and hugged a visibly agitated Mayweather in the corner, and he was escorted away so referee Joe Cortez could deduct a point for the foul. And that's where the real mess begins.

When Cortez brought the fighters back together—and called time-in—Ortiz once again went to hug Mayweather. Floyd, who clearly wasn't interested in the sudden love-fest, nailed Ortiz with a flush left hook, straight right combination that sent him to the mat and ended the night.

In the aftermath, both De La Hoya and Mayweather had some choice words about the outcome. Needless to say, they didn't agree. Oscar had this to say to Chris LaBate of BoxingScene.com:

If Mayweather has any honor, and I think he does, he will give Victor Ortiz a rematch. None of the champions I've faced would have taken advantage of the situation the way Floyd did. Everyone was cheated from a great fight. The fans were cheated...I think the referee needs to have control of the fight and I personally feel that he lost control in that fight. Call it legal or call it illegal, it was bad sportsmanship plain and simple and if Floyd has any sort of honor he will give Victor Ortiz a rematch.

You see, the thing about Mayweather is, he is a master of trash-talk, but even by those standards his response might have been below the belt:

Does Victoria Ortiz want another rematch because he thinks he can win or does he want another payday? Ortiz's idol is Oscar De La Hoya aka Golden Girl....fishnet....black pantyhose

If that were all, it'd be bad enough, but oh no, there was more:

I left the fight in the ring, but Oscar and Ortiz keep doing interviews crying like some Golden Girl b*tches. I will f*ck both of you up.

Oscar, knowing full well that his ability to fight Mayweather on these terms was limited, took to his Twitter account and instead tried to goad his foe in another way:

It's so sad Mayweather has to bash people and flaunt money he's not going to have when he retires. Give Ortiz a rematch. Try to beat him fair. And then, maybe I will give you another chance at me.

At this point, that'll never happen, but whenever the two share the same stage or arena or universe, you're never more than a few words from fireworks.

May 4, 2013: May Day

In the past, Oscar has been quick to pick against Mayweather heading into fights, only to explain away that pick after Floyd wins. 

Most recently he did it with Robert Guerrero. 

Heading into the fight, De La Hoya was quick to point out Mayweather's age and relative inactivity would allow Guerrero to outbox him and win a decision. Obviously that pick was about as wrong as you could possibly get, and De La Hoya was later critical of Guerrero for his game plan, and he was dismissive of Mayweather for the victory:

I was impressed with his footwork against Guerrero, but then again he fought Guerrero. But Guerrero fought the wrong fight with no game plan and that's the truth. Guerrero is one of the best fighters that I've seen in the last few years but he fought with the wrong game plan. And that's what I mean when I say 'he fought Guerrero' - a flat-footed Guerrero. Anybody could have outboxed Guerrero that night.

Call it sour grapes if you like, but it's become par for the course.



Present: The One

If Oscar has learned anything about picking against Floyd Mayweather, it doesn't show. If anything, he's going even more all-in with his bold predictions for this Saturday night's upcoming showdown between Mayweather and Canelo Alvarez. 

Canelo is Golden Boy's premier talent, and this time around at least, Oscar is finding a great deal of support in the media and amongst fans that his prediction of a Mayweather defeat will come true. 

In a recent interview with Kevin Iole of Yahoo Sports, "The Golden Boy" gave some insight into his feud with Mayweather, and maintained that, even six years later, he feels he deserved the decision in their fight.

The judges are not something he feels will matter come Saturday night, and he's predicting that not only will Canelo win, but he'll knock Mayweather out by the eighth round.

The animosity between the two men has built to a fevered pitch in recent weeks, and it appears on the verge of boiling over.

Mayweather apparently didn't take very kindly to hearing of De La Hoya's pick, and he responded to him in very personal terms in an interview with Lance Pugmire of the Los Angeles Times:

I feel like Oscar couldn’t beat the king so he wants to see someone else beat the king. It’s chess. … I can knock them all off the board. I’m amazing like that. Oscar’s just jealous of me. He don’t have money like me. He’s not flyer than me. Oscar ... likes to run around with this Golden Boy image, which we know  really is [false]. He’s always been jealous of me. I’m the total package.

The Golden Boy image to which Mayweather references is a shot at the public persona that Oscar De La Hoya maintains, which has, at times, been at odds with his battles against personal demons throughout his life.

De La Hoya has made no secret of his struggles with drugs and alcohol and that he will miss the fight in order to handle them.

Mayweather even went so far as to give all the credit for his success partnership in promoting fights to Golden Boy Promotions CEO Richard Schaefer whom he considered a "good guy" and not Oscar who he feels is not.

Schaefer, who is Swiss, says he often finds himself playing the neutral role between the two men, but he acknowledged that the rivalry is real, and it seems to be escalating. He told the Los Angeles Times:

I’m playing the Swiss role with this. Things are bad with them, and I hope they don’t boil over at Wednesday’s press conference...I just have to make sure it doesn’t get completely out of control. I think I’ll take a helmet with me to the press conference

With De La Hoya on the shelf now, due to his entering rehab, we now know what won't be a concern, but it will be interesting to see what Floyd Mayweather has to say about this development.