In the last 25 years, there have been exactly two non heavyweight fighters who were heavyweights at the box office, Sugar Ray Leonard and Oscar De La Hoya. The career's of Leonard and De La Hoya have many similarities. They were both Olympic Gold Medalist and media darlings. They both had crossover appeal, which enabled them to become a huge draw. And both Ray and Oscar have won title's in multiple weight classes. Another thing they share is that their career paths were mapped out, and ran like a fortune 500 company. In most of their big fights, they usually had the leverage. And it was assumed that they always got the benefit of the doubt from the fight judges.

Much has been said recently that the upcoming Hopkins-De La Hoya Middleweight Championship bout has many parallels to the Hagler-Leonard title fight back in April of 1987. That is definitely a fair comparison. In the Hagler-Leonard fight, Leonard was coming off a 35 month layoff. Hagler was the defending Middleweight Champ, who had just made his 12th successful title defense in the last six and a half years. Leonard fought as a Welterweight in his last fight, and was moving up to Middleweight.

Sugar Ray was one month shy of turning 31. He had already established himself as an all-time great fighter. A fight between Hagler and Leonard had been discussed off and on since 1982 when Leonard retired the first time due to a detached retina. When Leonard decided to challenge Hagler, he was in a no lose situation. He was coming off a long layoff, he wasn't taking any tune up fights, and he was moving up in weight. And on top of all that, Hagler was at the very least considered no worse than the third best pound-for-pound fighter in the world. Another thing Leonard was aware of was that Hagler had a very tough fight in his last outing against John “The Beast” Mugabi. Just maybe Ray sensed that if there ever was a right time to challenge Hagler, it was then. As long as Leonard didn't get killed or embarrass himself against Hagler, he had nothing to lose. However, if he won, it would be considered a monumental feat.

When Hagler and Leonard finally met, Leonard went on to win a very close controversial decision. The victory over Hagler is the signature win of Leonard's career, and it can never be taken away from him. Regardless of who you thought won, the fight was extremely close and Leonard is immortalized because of it.

I see De La Hoya in almost the same situation as Leonard was. As long as De La Hoya doesn't get destroyed by Hopkins, he can't lose. Much has been made of Oscar accepting a fight with Hopkins. Why I don't know, De La Hoya has always fought the best fighters. However, when you really think about it, what other option did De La Hoya have? And who else could he fight and make 30 million dollars, who he at least has a chance to upset.

No doubt De La Hoya's career is winding down. He has made more money than he'll ever spend. Finishing his career versus Hopkins makes all the sense in the world. Who was out there for him to fight? A third fight with Mosley certainly wasn't going to put 30 million in his pocket. Plus, Shane is a tough match up for him. Winky Wright isn't a big draw, and beating him wouldn't pave his way to immortality. Mayorga just lost to Spinks. Vernon Forrest is no draw or big accomplishment. And Trinidad is no where close to being ready for De La Hoya after his two year hiatus. No doubt Hopkins was the only fight that could pay him huge money, and provide him a chance to enhance his legacy.

Here's the plan. De La Hoya fights Felix Strum for the WBO Middleweight title. He'll most likely beat Strum which will give him his sixth title. Hopefully the rugged Robert Allen will give Hopkins a tough fight, and add some unwanted miles to Bernard's 39 year old body. Basically, De La Hoya had no choice but to accept a fight with Hopkins, because there wasn't any other mega fight out there for him.

Granted, De La Hoya has been more than willing to fight all the World's top fighters, but at this stage of his career, a fight with Hopkins makes the most sense for more than a few reasons. First of all, Hopkins is 39 years old and will only be months shy of turning 40. As much as I have raved over Hopkins being able to retain so much of his ability so late in his career, he could become an old man overnight without any warning. I'm not saying this is why De La Hoya agreed to the fight, or that Hopkins will erode significantly in the next 10 months, but the possibility cannot be discounted.

From a style standpoint, De La Hoya has a better chance to survive and go the distance than Felix Trinidad did. Tito's style was all wrong for Bernard. By taking the fight to Hopkins, Trinidad was set up to be takin apart. That doesn't apply to De La Hoya. What will work in Oscar's favor is, Hopkins is not a catch and kill fighter. He applies measured pressure. This will make it a little easier for De La Hoya to box, instead of having to fight. At least in the early going. Another thing is De La Hoya will be moving and up on his toes regardless of how Bernard fights. By De La Hoya moving, it will take longer for Hopkins to break him down.

This leads me to think that although De La Hoya won't win, he won't get demolished either. This is the best fight De La Hoya could've accepted at this stage of his career. I really don't think we'll see him fight again after Hopkins, regardless of the outcome. He has a chance to possibly cement his legacy versus an all-time great who just may not be at the top of his game. All these factors make this the ideal fight for De La Hoya. As long as Hopkins doesn't destroy him, it's a win-win for De La Hoya.

Writers Note

In recent columns I've compared the career's of Sugar Ray Leonard and Oscar De La Hoya. I want to make two things clear. When I rate Leonard and De La Hoya, I rate them as Welterweight's. I believe that's the weight where they were the most legit and natural. I know De La Hoya won titles at 130, 135, and 140. However, I believe when he fought at 130 & 135 he beat his opponents on the scales. The weigh ins for many of those title bouts were two and three days before the fights. Which means he was at 130 or 135 for all of two seconds, which gave him a tremendous advantage. When the fights took place, De La Hoya weighed up to 10 or 12 pounds more than his opponents. No way De La Hoya and Jorge Paez are the same size! I believe this was all pre-planned to help enhance De La Hoya's legacy. In reality, he was much bigger than Chavez also. Chavez was a natural jr. lightweight. And this is not being disrespectful of De La Hoya one bit. I give him his props and recognize his ring accomplishments. Oh, Leonard wasn't above doing the same thing. He won the light heavyweight title by forcing the champ Donny Lalonde to suck down to 168. Which no doubt weakened him and helped Leonard.

Lastly, I want to make it perfectly clear. In my opinion, Sugar Ray Leonard would've beat De La Hoya seven days a week, 52 weeks a year. Too me, Leonard is a level above De La Hoya as a fighter. I have no doubt that Ray at his best would have defeated every fighter De La Hoya ever fought. I can't say the same about De La Hoya. I have serious doubts if he would have got by Duran of 1980. And I'd bet my life that Hearns of 1981, and Hagler of 1987 both would have stopped him. In my opinion, Leonard was the second best Welterweight of all time. Ranking only behind Sugar Ray Robinson. As outstanding as De La Hoya has been, I'm not sure he cracks the top ten Welterweights in history. Possibly, but definitely not a given.