Oscar De La Hoya: 5 All-Time Greats He Could Have Beaten in His Prime

The Golden Boy had it all.

The million dollar smile, movie star looks, Grammy award-winning voice, charming personality, heartwarming background story and Olympic Gold medal all combined to make Oscar De La Hoya the biggest draw and brightest star (south of the heavyweight division) in the history of boxing.

The legacy of De La Hoya the celebrity is safely secured.

The same can not be said for the legacy of De La Hoya the fighter. 

A career based in "what ifs" is marred by the final three round against Felix Trinidad, two possibly steroid-induced losses to Shane Mosley and all-too-late battles against Floyd Mayweather, Jr. and Manny Pacquiao.

Throughout his career De La Hoya was always considered a pound-for-pound contender, although he never actually beat an in-his-prime opponent, and for a fighter who is assured to be a first ballot Hall of Famer, his career-defining victories came against aging stars Julio Cesar Chavez, Pernell Whitaker and a volatile, yet not so great Fernando Vargas. 

However, De La Hoya wasn't all glitz and glam. His lead left hook was devastating and his combination of speed and power matches up with any all-time great.  

In a career filled with "what ifs" Oscar De La Hoya's talent and ability will always be up for debate. Was he truly great enough to rank with "Sugar" Ray Leonard and "Sugar" Ray Robinson, or was he a very talented fighter with a nice smile who wasn't as good as we wanted him to be?

With that in mind, here's five all-time greats "The Golden Boy" could have beaten.    

5. Miguel Cotto

The status of Miguel Cotto as an all-time great is surely debatable, but for a four- to five-year stretch he was considered one of the pound-for-pound best fighters in the world. If he had faced a prime Oscar De La Hoya at 147 it would have been a difficult night for the Cotto. 

In almost every facet of the game De La Hoya outshines Cotto. Using his speed, reach, height and considerable power, De La Hoya presumably would outclass Cotto over the series of 12 rounds. As we've seen in the past, Cotto doesn't deal well with speed.

Barring a few exchanges, as De La Hoya was prone to enter, it would be a relatively easy night for the "Golden Boy."   

4. Alexis Arguello

A fight with one of the best 130-135 pounders, Alexis Arguello would present an opportunity for De La Hoya to use his speed and movement and secure a decision victory.

Arguello's body and style of accurate power punching, yet laboring movement, has always reminded me of Felix Trinidad and that wouldn't spell good news for the Nicaraguan star.

If you have a functioning set of eyes, you may remember that for nine rounds De La Hoya outboxed, outsmarted and outmaneuvered the Arguello carbon copy, seemingly on his way to a dominate victory. And yes, we all know De La Hoya threw away the last three rounds, but that's for another day. 

For a man who has a history of struggling with faster and quicker opponents (like Aaron Pryor) a matchup with the "Golden Boy" would be a long night for Arguello.

As long as Jerry Roth and Bob Logist aren't judging the fight.   

3. Floyd Mayweather, Jr.

Could Oscar De La Hoya, in his prime, have defeated Floyd Mayweather, Jr.? 

He definitely could. 

While I'm not confident enough to claim De La Hoya would have beaten Mayweather in both their primes, De La Hoya had the boxing abilities to compete with Mayweather. Given a few opportunities to exchange and steal rounds, he could have very well have beaten the "Pretty Boy" on occasions. 

The one thing that De La Hoya lacked in their 2007 fight was the speed and reflexes to deal with Mayweather. At no time in his career did De La Hoya possess reflexes or speed to match Mayweather, but a 1997-2000 "Golden Boy" would have had the speed to give Mayweather a much more difficult fight than in their actual fight.

While I'm sure who would have won, it would have made for an amazing show and fight. 

2. Julio Cesar Chavez

He did it twice, and I strongly belief that if they fought 10 times De La Hoya would win a majority of those bouts. 

While their paths never crossed perfectly, with their two fights coming near the twilight of Chavez's career, De La Hoya attempted to cast himself out of the shadows of the Mexican great with bouts in 1996 and 1998. 

Both ended in brutal displays of De La Hoya's dominance.

While many will point to those as meaningless outcomes—coming far too late in Chavez's career for any real impact—I say that styles and size make fights.

At any weight class De La Hoya would be too big, too fast and too strong for Chavez. 

At both 140 and 147 De La Hoya was too much for the smaller Chavez to handle, and in most cases Chavez struggled at those weights (although the results didn't always bear that out—Medlrick Taylor, Pernell Whitaker).

The same would hold true at lighter weights, where De La Hoya's boxing ability and movement would thwart the offensive attack of Chavez in a similar form of the Whitaker fight.   

1. Roberto Duran

I may take a bunch of heat for this one, but at lightweight I could see Oscar De La Hoya beating what many consider the greatest lightweight of all time, Roberto Duran. 

I'm not crazy and I'm not a "De La Hoya fan who knows nothing about boxing." In order to understand my reasoning we'll take a look at Duran's resume, his strengths and weaknesses, as well as his three fights with "Sugar" Ray Leonard.

In what I've always found quite surprising—for a fighter generally regarded as one of the greatest lightweights of all time—is the lack of great quality opponents Duran defeated in his career. Besides the obvious Leonard victory, which I'll touch on later, Duran's greatest victories came against Ken Buchanan, Pipino Cuevas and Iran Barkley (wake me up if you fell asleep). Comparing that to the long line of opponents Duran lost to, albeit at higher weight classes, and Duran doesn't seem as infallible as many make him out to be.

Next, Duran's inability to deal with elite taller fighters with an extended reach advantage would present problems against 5'10" De La Hoya. Blessed with one of the better jabs in the sport, De La Hoya could keep Duran at bay and out of range.

Finally, the best place to look in defending De La Hoya's chances against Duran would come in the form of the three Leonard-Duran fights.

Using his superior boxing ability, speed and movement, Leonard was able to dominate Duran leading to the famous "No Mas" in their second fighting.

While, De La Hoya is no "Sugar" Ray Leonard, the boxing, speed and movement advantages all remain the same for him. If De La Hoya is able to refrain from the brawling tatics, in which Leonard was all too willing to oblige Duran in their opening meeting, he could very well win.