One fought in the 1976 Olympics with his girlfriend's picture taped to his boxing shoe, the other dedicated his 1992 Olympic performance to the memory of his recently deceased mother. Both were chronicled by the media and the TV networks. They both won Gold Medals and flashed Pepsodent smiles. Both won several professional world titles and called the shots as to the path their careers would take. Some felt they were both condescending and, interestingly, both were promoted by Bob Arum. The parallels between Sugar Ray Leonard and Oscar De La Hoya are certainly eerie. Here's another. Leonard and De La Hoya both followed two of the most popular and controversial heavyweight champions in boxing history. Leonard followed Muhammad Ali and De La Hoya followed Mike Tyson. Both Ray and Oscar were heavyweights at the box office as well. These two superstars had crossover appeal and drew more than just boxing fans to their fights. When they fought, the opponent didn't matter. Fans came out to see them.
When analyzing their boxing styles there are some differences. As far as left jabs go, De La Hoya gets the nod. However they used their jabs differently, Leonard's was faster and sharper, but he used it more to set up his right hand and to hook off of. De La Hoya's jab was actually a major part of his offense and is his overall best punch. Leonard certainly had the better right hand and the better uppercut. When it comes to who had the better left hook, it's a toss up. De La Hoya had the better hook to the body, but Leonard had the better hook to the head, and Ray was definitely a better finisher than Oscar. Sugar Ray was the much faster fighter of both hand and foot, and was the more fluid technician. Oscar is more robotic and herky jerky. One style trait Ray and Oscar shared was the ability to adapt to all different styles and change their strategy during the course of the fight as they saw fit.
Sugar Ray was the better puncher, he stopped bigger and better fighters in Benitez, Duran, Hearns, and Lalonde. De La Hoya never has KO'd any fighter as devastatingly as Leonard did Davey "Boy" Green, and Andy "Hawk" Price, who defeated both current champions at the time, Carlos Palomino and Pipino Cuevas. The best fighters De LaHoya stopped are Chavez and Vargas. As to who has shown better stamina, again this favors Leonard. Ray demonstrated that by stopping Benitez in round 15 and Hearns in round 14, endurance was never a problem. Oscar's latest stoppage came against Fernando Vargas in the 11th round. De La Hoya never had to fight more than 12 rounds, unlike Leonard who fought wars with Duran for 15 rounds and Hearns for 14. Maybe De La Hoya's endurance was close to being on par with Leonard's but, it definitely cannot be regarded as better.
Leonard definitely fought the better punchers, and was only stopped by Hector Camacho in his last fight when he was 41 years old and hadn't fought in over six years. De La Hoya has never been stopped, but he has only faced two legitimate punchers in Quartey and Trinidad, who don't quite measure up to Hearns, Hagler and Norris. Quartey had him down but, Trinidad never really caught Oscar with his Sunday best. The jury is still somewhat out on De La Hoya's chin, but from what we've seen, it's certainly hasn't been a liability. Regarding Leonard, there can be no denying that he fought punchers who tested his chin. Other than Hearns, no one came close to hurting him until he fought Terry Norris when he was 3 months shy of his 36th birthday. What is certain is that Leonard had a great chin, and has to get the verdict over De La Hoya regarding who took a better punch.
One of the comparisons usually made when comparing great fighters is who fought and defeated the better fighters during their career. Oscar De La Hoya is one of the few current fighters who has actually fought the best available of his generation. However, Sugar Ray Leonard also fought the best of his era. The big advantage Leonard had is that there were more great fighters in the late 70's throughout the 1980's compared to the 1990's through 2003. Leonard's wins over Benitez, Duran, Hearns, and Hagler far outweigh De La Hoya's wins over Chavez, Whitaker, Quartey, and Vargas. Both have defeated other outstanding fighters, however I just listed the best of the best who they hold wins over.
Who would have won
For anyone who watched the career of both fighters, it's just about impossible not to realize that Leonard would've had to have been favored to beat De La Hoya. The problem for Oscar is that there is nothing he could confront Leonard with that he hasn't shown that he couldn't overcome. As good as De La Hoya's jab is, Leonard confronted and overcame a faster, longer, and harder one when he fought Hearns, and Oscar doesn't have the right hand behind his that Hearns carried. It's impossible to envision De La Hoya out boxing Leonard, he just doesn't have the speed or skill, and Leonard wasn't out-boxed by Benitez who was more slick and elusive than De La Hoya. There is no way Oscar could hit Ray as hard as either Hagler, Hearns, or Norris, and they weren't able to stop him. De La Hoya isn't nearly as tenacious as Duran or Hagler, and Ray wasn't overcome by their tenacity.
Looking at it from De La Hoya's perspective, he hasn't fought anyone close to Leonard. He's never fought anyone with the combined speed and power and boxing ability of Sugar Ray. Yes, Trinidad hit harder but, wasn't nearly as fast or complete as Leonard. Whitaker was a cutey, but he didn't have the speed or power to make De La Hoya pay for missing punches like Leonard would, and Whitaker was smaller than Ray who was a true welterweight. De La Hoya faced Quartey's jab which was harder than Leonard's but not nearly as fast, and Quartey had no right hand behind his jab like Leonard did. There is absolutely no way that even the most ardent De La Hoya fan can say Oscar ever fought anyone close to being the overall fighter as Sugar Ray Leonard, not one!
I just don't see any way that Leonard isn't an overwhelming favorite over De La Hoya if they fought at 147 or 154. Leonard has the advantage just about everywhere one fighter could have over another. There can be no debate that Leonard was the faster fighter, a superior boxer, and overall better puncher. It also can't be disputed that Leonard fought and defeated better fighters during his career than De La Hoya has. Even if De La Hoya fought and defeated Bernard Hopkins, (and that's a monumental reach) Leonard would still have the better resume. I just cannot see any way that Leonard would lose to De La Hoya had they fought on their best night.
On September 16th 1981, Sugar Ray Leonard and Thomas Hearns met in what was the most anticipated welterweight championship fight in history. On September 18th 1999, Oscar De La Hoya and Felix Trinidad met in what was the most anticipated welterweight championship fight since Leonard-Hearns. It would be very hard to argue that Leonard, Hearns, De La Hoya, and Trinidad aren't four of the best welterweights since 1980. Earlier I matched the two best punchers from these two fights in Hearns and Trinidad, and concluded that Hearns was the better fighter and should be ranked above Trinidad, in my opinion. When evaluating Hearns and Trinidad, I found that the more I dug into their careers, the wider the gap grew between them favoring Hearns. In this article I evaluated Leonard and De La Hoya, the two superstars from those two super-fights and have concluded Leonard was the better fighter. This went somewhat like the Hearns-Trinidad comparison.
The more I looked into their careers, the more the gap grew favoring Leonard. I feel overwhelmingly that Leonard is superior to De La Hoya, even more than I feel Hearns is superior to Trinidad. In a Hearns-Trinidad match-up, it's not out of the question that Trinidad may have been able to beat Hearns. I would definitely pick Hearns to win but it's not a mortal lock. However, regarding Leonard and De La Hoya, in my opinion it is a mortal lock that Leonard would beat De La Hoya every time. I just can't envision any scenario where De La Hoya wins, even once. In rating the four fighters 1-through -4, I would say Leonard is clearly 1, Hearns is definitely 2, and the jury is still out on 3 & 4 between De La Hoya and Trinidad. I will say that I have no doubt that the fighters of the 80's below heavyweight are better than the fighters of the 90's through 2003 below heavyweight!