The career parallels of Oscar De La Hoya and Sugar Ray Leonard are very similar. Forget the star treatment, image, and perceived cockiness. The fact is both De La Hoya and Leonard could flat-out fight. They also were tough and usually strived to fight the best of the best of their generation. Sure, they had some cup-cakes, what fighter hasn't, but a majority of their fights once they were ranked were versus the upper-tier fighters of their era.

Oscar and Ray also collected many titles and endorsements along the way. The biggest difference I see, other than the fact that I think Leonard was the better and more complete fighter, is Leonard has more signature wins. To this day I'm not sure what fight is Oscar's signature victory. Unlike Ray, who has three or four.

Another thing De La Hoya and Leonard share is that they both moved up in weight from where they won their first title and won titles in several weight divisions. This is something that they are both known for. However, the biggest bond between De La Hoya and Leonard is about four months from being realized.

Provided De La Hoya gets by his next opponent, Felix Strum, this Saturday night, he is scheduled to fight Undisputed Middleweight Champ Bernard Hopkins on September 18th. Hopkins has ruled the Middleweight division for the past eleven years, and is also unbeaten in those eleven years. On top of that, he's made a record 17 title defenses, and it should be 18 by the time he fights De La Hoya. This is assuming that Hopkins beats Robert Allen on the De La Hoya-Strum co-main event.
Sugar Ray Leonard also tangled with a great Middleweight back in April of 1987. Marvin Hagler was his name. And he was also unbeaten in 11 years and made 12 consecutive defenses of the Middleweight title that he owned for seven years. In fact, Hagler was even more feared than Hopkins is today. Hopkins is respected as much as Hagler was, but he wasn't perceived to be as unbeatable.

Like Leonard, De La Hoya will be a big underdog versus Hopkins. Hopkins is a complete fighter who can adapt to all styles in the ring. And like Hagler, he is super-tough mentally with tremendous stamina guided by an all-time great chin. On top of that, Hopkins looks at De La Hoya the way Hagler looked at Leonard. Hagler longed to fight Leonard because he was overshadowed by him during his career. Due to Leonard having more crossover appeal and star power, he made much more money and was treated as boxing's true Superstar. This is something Hagler resented, and only added more fuel to the burning desire he had to face Leonard.

The exact same things apply to Hopkins regarding De La Hoya. Like Leonard did Hagler, De La Hoya has overshadowed Hopkins since he turned pro. De La Hoya has always received the huge pay days and Rock Star treatment, just as Leonard did. Hopkins views De La Hoya as his ticket to finally getting the Millions he so deserves. Bernard gained much respect when he took Felix Trinidad apart, but the star treatment and Millions didn't follow. Like Hagler, Hopkins is a fighter to the core. Like Leonard, De La Hoya is a star and a fighter.

When Ray Leonard challenged Marvin Hagler, he was mocked and ridiculed for even thinking he could beat a legendary Champion like Hagler, especially after never fighting above 154 pounds. On top of that, Leonard had only fought once in the past five years, almost to the day. However, what many overlooked was the fact that Leonard studied Hagler and waited for the slightest signs of slippage to appear. In Hagler's last fight prior to fighting Leonard he fought John “The Beast” Mugabi. Mugabi gave Hagler one tough fight and afterward Hagler started talking retirement. It was at that point where Leonard sensed Hagler was vulnerable and made him an offer he couldn't refuse. No doubt Hagler could not walk away from a fight with Leonard, even if he knew he wasn't at his peak.

Sugar Ray Leonard was a master at breaking down the style of his opponents. The only time he really erred was in the first Duran fight where he went toe-to-toe with Roberto. However, that was more ego than anything else. Something you knew wasn't going to happen with Hagler. Leonard was just too smart and shrewd for that.
Another thing Leonard had going for him was that he had the skills to fight Hagler, and the boxing insight on how to execute his fight plan. Many fighters and observers thought the way to fight Hagler was to back him up. The problem with that was Hagler was a counter-puncher. He feasted on fighters who took the fight to him. The only fighter who went the limit with Hagler in a title fight prior to Leonard, was Roberto Duran in November of 1983. Duran pulled this off by moving away from Hagler and drawing him in. Duran knew he wasn't strong enough to pressure Hagler, so he opted for a style that he thought gave him the best chance.

During their fight, Duran found Hagler easy to reach with lead right hands and counters after Hagler committed to throwing. Leonard was ringside for this fight and saw how Duran who was shorter and slower than him, with no lateral movement made Hagler miss and beat him to the punch in many exchanges. Leonard knew if he moved to the left and forced Hagler to be the Joe Frazier in the fight, he had a good shot to decision him.

Leonard actually dictated the pace versus Hagler, forcing him to use a large portion of the rounds trying to track him down and corner him. In the meantime, Leonard was launching three and four punch flurries at Hagler, breaking up his rhythm and momentum. Another thing Leonard exposed was that Hagler didn't cut off the ring very well. He followed Leonard and never really won any of the exchanges until Ray slowed down. This cost him a very close split decision defeat.

The fight was very close and fans of both fighters thought without question that their man won. For the Record, I gave Leonard the first three rounds and gave Hagler five of the next nine for a total of 7-5 Leonard. I'm a fan of both fighters, but thought Leonard pulled it out. Although I have no problem with anyone who felt Hagler won it. It was very close either way.

The bottom line is Leonard knew how to fight Hagler, which enabled him to pull off a victory that can never be taken away from him. He just knew how to fight Hagler and knew that he had the skills to capitalize on Hagler's vulnerability of pressing the fight.
Recently I saw Oscar De La Hoya interviewed on Comcastsportsnet. He was asked what he saw in Hopkins that makes him think he can beat him. De La Hoya responded saying I definitely see something, but I'm not going to tell you or anyone else. What I can't figure out is what it is that he sees. I was one of the few who thought Leonard would decision Hagler. I know everybody says that now, but I really did and won a good piece of change getting 4-1 odds.

That being said, I think De La Hoya has a task equal to Leonard's in front of him. I just can't see how Oscar can pull this off unless Hopkins becomes an empty package in the next few months due to his advanced age of 39. From a style vantage point, I can see De La Hoya surviving versus Hopkins and going the distance. Mainly because he'll be moving away from Hopkins like Joppy did. Unlike Trinidad who took the fight to Hopkins which enabled Hopkins to set him up and break him down.

Unlike the Hagler-Leonard fight, I like the favorite Hopkins in this one. I just think he's too versatile to lose to De La Hoya. Plus he's bigger and stronger and I can't envision De La Hoya hurting Hopkins. Wonder what it is that De La Hoya sees? Whatever it is, I've certainly missed it.