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The Mega-Fight Edition [Vol.VII]: Oscar De La Hoya's Double Take

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The year is 2014, and it’s easy to hate Oscar De La Hoya.

There are those who feel he turned his back on Saul Canelo Alvarez on the eve of his mega-bout with Floyd Mayweather.

As such, perhaps it’s easy to love that he’s in some sort of drug addicted fog, unable to shake demons that only he and the angels are aware of.

We don’t know.

The world caught images of him in lurid fishnet stockings and high heels in a way that had me thinking he was on some sort of acid or heavy hallucinogen, because I just can’t dream up a scenario in which a fighter fantasizes about being a hooker- or somebody’s bitch. That moment in time is full of ambiguity.

Maybe those pictures conveyed a message he didn’t intend. Never-the-less, I have enough images of him strung together with a mouthpiece in his mouth and a pair of gloves on. Snapshots of picturesque left-hooks delivered with devastating effect. He was a pretty boy full of bad intentions in the ring.

I also have enough images of two fighters he faced that really didn’t want to face him again.


It was Benjamin Franklin who told us to “either write something worth reading, or do something worth writing about”, and as such, it should be noted that De La Hoya has done both the world over.

The “Golden Boy”, the 1992 Olympic Gold Medalist and former multi-division world champion, turned himself into a writer by default given his long history of print worthy quotes and penchant for dramatic tone. His Golden Boy Enterprises owns THE RING, which is the most influential publication for boxing on the planet.

So you can even say he “owns” his own title belt.

He is the most successful fighter in the history of the sport and the most accomplished athlete of Mexican descent in the history of the world.

Oscar De La Hoya was a “great” fighter.

An out of shape De La Hoya really didn’t beat Felix Sturm, and an in shape De La Hoya really lost to Pernell Whitaker. He vanquished the great Chavez, beat Ike Quartey in an epic affair and challenged Shane Mosley in his prime. He challenged Hopkins only to fall short of that mountain and was avalanched by Pacquiao.

He also beat Felix Trinidad and scared the hell out of Floyd Mayweather.

But that was then- and this would be now- back then.


I’ll never forget watching their fight at a friend’s packed house party in Queens, NY. We all know how Oscar decided to not fight in the championship rounds of that fight and subsequently lost.

In retrospect, he deserved to lose for not closing the show in a fight of such magnitude.

As he walked back to the dressing room, he could be heard and seen in demonstrably angry fashion. “I f*cking gave him a Boxing lesson! This is bullsh*t! There’s no way I lost that f*cking fight!”

That it never happened again is a travesty.

Much has been said about why it never did come to fruition; among the reasons being that Oscar was afraid to face him again. That just doesn’t make any sense, for Oscar never ran from anyone in his career and has one of the most incredible resumes of any champion in boxing history.

Look at who Oscar fought from the year 2000 to 2004 and that argument becomes ridiculous.

This fight was a poster child for a major turning point in boxing, and firmly established that fights could either be made- or not made- based on numbers. De La Hoya refused to budge, but Tito would make give ground and budge constantly in a rematch.

Trinidad was absolutely lethal. He was fearless, and released the type of systematic ultra-aggression not really seen before from an offensive fighter. Armed with the knowledge of how De La Hoya finished his initial fight with him, Trinidad would stalk and strike from the start.

But De La Hoya was a very well rounded fighter under Floyd Mayweather Sr., and would have been better equipped to deal with Trinidad in many ways. It is a much more spectacular fight than its predecessor, and as was the case in his rematches with Chavez and Mosley (De La Hoya beat Mosley the 2nd time), Oscar would have fought a much better fight.

He faces danger and gets struck in ways like never before- maybe even hitting the canvas. Still, De La Hoya would follow enough of Floyd Sr.’s script to out-box Trinidad for a UD win.


This fight almost featured something that would have actually been a travesty had it happened. Floyd Mayweather Sr. was this close to training De La Hoya for their epic encounter in May 2007, and would have absolutely trained Oscar for the rematch that never was.

I cannot prove this, but I believe Mayweather “retired” in December 2007 following a tumultuous battle with Ricky Hatton to avoid that fight (along with a few others). De La Hoya was and always would be a very bad style match-up for Mayweather, and this would’ve been exacerbated if “The Golden Boy” was prepared for “Money” by his father.

Oscar De La Hoya would’ve beaten Floyd Mayweather in a rematch, and pretty soundly at that.

Freddie Roach did an admirable job with Oscar for Floyd, who hasn’t faced Freddie since (and doesn’t want it with Robert Garcia trained fighters either), but his dad understands him in ways no one does- including his Uncle Roger.

Oscar would be to Floyd what Marquez was to Pacquiao, and it goes to Floyd’s understanding of his limitations and Pacquiao’s determined resolve, when you offer a comparison.

There is no better example of styles making fights when you study the contrasts of these two rivalries, for Oscar is as taylor made for Pacquiao as Marquez is for Floyd.

Floyd knew this, which is why he avoided Oscar, and it’s the same reason he’s dead set on avoiding Pacquiao.

You cannot wait on Floyd at all, and he must not be given comfort in the ring. He must be made to fight for 3 minutes of every round. If you allow him room to operate or decide to be a counter puncher at all- you will lose.

Floyd Sr. would devise a plan that called for Oscar to fight Floyd “tall” and to come forward at all times behind a consistent jab, or get his ass cussed out in between rounds. My guess is he’d be called everything except a child of God after every round while really beating Floyd and winning most of the exchanges.

The real “blueprint” to beating Floyd was left by Jose Luis Castillo- who was never as talented as Oscar. Mayweather Sr. would create a much more refined version of that fighter in De La Hoya, who would win a very clear UD over Floyd.


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