For two fighters from two different eras, Sugar Ray Leonard and Oscar De La Hoya sure have drawn a lot of comparisons with each other.  And for good reason.  In a sport as violent as boxing, making a prizefighter into a truly marketable figure can be a tough sell.  On occasion, though, a boxer is able to overcome the negative stereotypes surrounding the sport by virtue of charisma, shrewd business sense, and wise handlers guiding their every step.

Leonard and De La Hoya were two such fighters.  Both fighters' careers followed remarkably similar paths early on, which led to the same destination:  superstardom beyond the ring ropes.

But this scenario begs the question, which fighter casts the bigger shadow?  It's a difficult question to be sure, particularly since De La Hoya's career is still ongoing.  Still, it's a worthy debate.  If the boxing world as we know it came crashing down tomorrow, whose legacy would better stand the test of time?

The Case for Leonard:

From the moment of his emergence on the international stage at the 1976 Olympic Games in Montreal, Ray Leonard radiated with star quality.  It was easy to see then that he was the complete package.  With his girlfriend's picture taped to his shoe as he boxed in the Olympic final against favored Cuban Andres Aldama, Leonard set himself apart as one of the captivating human interest stories of the Games.  His improbable victory to claim the gold medal made his star shine that much more.

After retiring following his Olympic glory (the first of several retirements as it would turn out), Leonard's professional career exhibited all the promise indicated in his amateur days.  With legendary trainer Angelo Dundee at the helm, Leonard progressed through the ranks at an accelerated pace to defeat Wilfred Benitez for his first world title less than three years after his pro debut.

Leonard's career continued on like a Hollywood screenplay.  After losing a tough decision to fellow great Roberto Duran, Leonard returned five months later to frustrate Duran into quitting.

Less than a year later, Leonard found himself across the ring from the seemingly invincible Thomas Hearns.  In the unexpected and unfamiliar position of being thoroughly outboxed, Leonard rallied to stop an exhausted Hearns in the fourteenth round of a fight for the ages.

Nagging injuries due to complications from a detached retina stalled Leonard's career until he came out of retirement in 1987 to fight middleweight champion Marvin Hagler.  Leonard's flashy combinations were enough to gain him a highly controversial split decision over a disgusted Hagler.

In the end, Leonard's career was defined by wins over the best fighters of his era.  Of course these wins helped his bank account, as he became the first boxer to accumulate $100 million in earnings, along with countless endorsement deals.

Another impressive statistic is how brief Ray Leonard's prime really was.  Of his 40 career fights, 33 of them took place in the first five years of his professional career, with the remaining seven scattered over the next fifteen years.  That relatively brief time in the sun was still enough to make Leonard one of the game's immortals and a permanent household name.

The Case Against Leonard:

Upon closer examination, Leonard's sterling career shines brightest only in the correct lighting.  His accomplished record of 36-3-1 (25) seems a little dingier when we go beyond the numbers.

In what was perhaps his greatest victory against Thomas Hearns, Leonard didn't offer the courtesy that he received against Roberto Duran by giving Hearns an immediate rematch.    This could be blamed in part on the detached retina that surfaced shortly after the win over Hearns, but it also seems that it came out of sheer reluctance on Leonard's part to step back in the ring against a man who had put him through hell.

The rematch had to wait eight long years, when both men were past their primes.  Even then, Leonard was dropped twice and was lucky to escape with a draw.

Against Marvin Hagler, Leonard won the fight more so with gamesmanship than grit.  His round-stealing flurries won many rounds which could have gone to Hagler for his steady aggression.  The mere discussion of this fight will cause more arguments than any big fight of the last thirty years.  The win over Hagler was far from clear-cut, and along with the draw against Hearns, could conceivably be seen as a blemish on Leonard's record.

Beyond the two fights Leonard could have lost, it's worth discussing two that he actually did lose.  His ill-advised comeback in 1991 against a prime Terry Norris saw Leonard take perhaps the worst beating of his career as he was dominated by a fresher, stronger fighter.

The Norris debacle should have been a signal to Leonard that his time was up, but the loss was certainly forgivable, especially considering Norris' long tenure atop the division following the fight.  However, Leonard's 1997 comeback against Hector Camacho, Sr. was simply foolhardy.  Then forty (going on forty-one), Leonard was embarrassed and stopped by the smaller, light-hitting, Camacho, who was also past his prime.

That his last two fights were two convincing losses as a result of two risky comebacks can only be seen as blemishes to Leonard's legacy.  And considering his close calls against both Hearns and Hagler, Leonard's apparent supremacy during his era doesn't quite hold up as strongly as it might seem.

The Case for De La Hoya:

Oscar De La Hoya's time in the public eye began in a manner extremely similar to Leonard's.  At the 1992 Barcelona Olympics, De La Hoya did the unexpected in claiming the only boxing gold medal for the United States, this after coming to terms with the loss of his beloved mother Cecelia to cancer.  It didn't take a genius to see the star potential in De La Hoya, with his matinée idol looks and well-spoken charm.

Like Leonard, De La Hoya's professional career began with much celebration and fanfare.  De La Hoya was already headlining nationally televised fight cards by his third pro fight.  In his twelfth fight, and after less than sixteen months as a professional, he found himself in his first title fight.

This was just a warm-up for The Golden Boy, as big names soon began to pile up on his record.  Before long, he owned wins over Rafael Ruelas, Genaro Hernandez, Miguel Angel Gonzales, Julio Cesar Chavez, Pernell Whitaker, Hector Camacho (ironically following his stoppage of Leonard), and Ike Quartey.  Keep in mind that this was all by the time he turned twenty-six.

By this time, the Oscar De La Hoya express had long left the station.  He was so popular in the fight mecca of Las Vegas that it became his home away from home.  Oscar's broad appeal made fight fans outside of boxing's typical target market.  While it may have once seemed impossible, De La Hoya's star seemed to have superseded Leonard's.

The fact that De La Hoya suffered a handful of defeats in recent years has done absolutely nothing to adversely affect his earning power.  His most recent effort, a dominant if uninspiring performance against Steve Forbes, was enough to sell out a 27,000 seat outdoor soccer venue.  Some say that a fighter's punch is the last thing to leave him.  That's not true.  A famous name will last even longer.

The Case Against De La Hoya:

While Leonard's career was defined by victories, controversial or not, over the era's best fighters, De La Hoya's career may end up being defined by losses to this generation's best.  His slightly less-than-glittering 39-5 (30) record is indicative of such.

Sure, his loss to Felix Trinidad was questionable at best and a travesty at worst, but De La Hoya can only point the finger at himself for the defeat.  After fighting arguably the best eight rounds of his career, De La Hoya traded glory for track spikes as he raced around the ring for the final four rounds.  Trinidad may have been the recipient of charity, but it was De La Hoya who was in the giving mood.

His second defeat was a legitimate one at the hands of Shane Mosley.  In that encounter, De La Hoya was simply outhustled and outfought.  The loss in the rematch to Mosley, however, falls in the same category as the Trinidad fight:  questionable.  Again, though, the loss in the Mosley rematch came as the result of another late-round fade by Oscar.

His next loss came in a bad decision to fight long-standing middleweight kingpin Bernard Hopkins.  Though he hung with Hopkins early, flash and class weren't enough to beat the naturally bigger man.

His most recent loss against Floyd Mayweather was a respectable performance, though Oscar once again did just enough to lose a close fight.  Once again, a noticeable slowdown late in the fight seemed to be the difference.

On the surface, though he has five losses, three of them are open to discussion.  But even if we are charitable to Oscar in his losses, some of his victories are also open to the same scrutiny as his losses.

His win over Pernell Whitaker, though wide on the judges' scorecards, was hardly a wipeout if objectively witnessed as it took place.  The disturbingly wide margins had many people wondering if homecooking was to blame, especially since more than a few observers scored it a draw or even a close nod for Whitaker.

Oscar's split decision over Ike Quartey seemed well-earned after the phenomenal twelfth round he put forth, dropping and nearly stopping the undefeated Ghanaian.  What people don't remember, however, are the long stretches in the middle rounds when Quartey seemed to be dominating De La Hoya, including a sixth round when the fighters exchanged knockdowns, but Quartey seemed to do the greater damage.

Then there was the Felix Sturm incident, when a spongy, out of shape De La Hoya fought like hell to earn a hotly disputed decision over the unbeaten, but unknown Sturm.

Suddenly it seems like Oscar should be happy with the five losses on his record.

The upside for Oscar is that a win in September against pound-for-pound king Floyd Mayweather could give his legacy one last boost before he calls it a day.  However, it's difficult to imagine that one win against a great fighter in his prime could undo losses in five other significant fights.

It's a tough debate.  Here we have two great fighters who have transcended the sport to become crossover superstars.  That's a rare feat for any athlete, much less a professional fighter.  One man is already enshrined in the Hall of Fame, and the other surely has his place awaiting him.

But the question remains, TSS Universe, which fighter casts the bigger shadow?  Who will be remembered for generations down the line as the better man?  Weigh in with what you think, is it Sugar Ray or The Golden Boy?