Oscar De La Hoya boxed professionally from 1992 to 2008. In that time, Mr. De La Hoya won 11 titles in six weight classes, was recognized as Ring Magazine’s 1995 fighter of the year and became one of boxing’s most lucrative pay-per-view draws. He is the founder, Chairman, and CEO of Golden Boy Promotions, one of boxing’s largest promotion companies. One might think at age 48 and more than 12 years removed from his last fight – which did not end well – he would be content in retirement. One, apparently, would think wrong. Below, I examine Mr. De La Hoya’s planned comeback from retirement and offer some additional thoughts on poorly advised sports comebacks.

Illustration of Tom Johnson vs Isaac Perkins in a 1789 boxing match in England, clipped from "Pulilistica: The History of British Boxing"
Sketch of 1789 fight between Tom Johnson and Isaac Perkins in Oxfordshire – clipped from “PUGILISTICA: THE HISTORY OF BRITISH BOXING

Oscar De La Hoya’s Possible Comeback From Retirement

On March 26, 2021, Mr. De La Hoya announced that he would end his long retirement for a fight on July 3, 2021. Mr. De La Hoya has floated the idea for several months. In a November interview, he stated that had wanted to see how the exhibition match between Mike Tyson and Roy Jones went before finalizing his decision, noting that both of those gentlemen were only slightly older than him. Apparently, Mr. De La Hoya was satisfied. However, lest one thinks that he too is looking for a mere exhibition fight, Mr. De La Hoya suggested current hard-punching middleweight titlist Gennady Golovokin as a potential opponent.

Given his size and punching power, Mr. Golovokin would have been a very difficult opponent for Mr. De La Hoya, who is not a natural middleweight, 15 years ago. I do not suppose that the match-up would be better now for him.

The Circumstances of Oscar De La Hoya’s Retirement

One might ask what the circumstances of Mr. De La Hoya’s 2008 retirement were. After all, not all retirements are created equal. Perhaps Mr. De La Hoya retired at his peak, rode off into the sunset with a great victory, and is refreshed and ready to pick up where he left off as he approaches age 50.

That is not quite the case. Let us review his last three fights.

Mayweather-De La Hoya

On May 5, 2007, Mr. De La Hoya engaged in a mega-fight against Floyd Mayweather, who was recognized as the best fighter in boxing, but was moving up in weight to challenge Mr. De La Hoya as a junior middleweight. Mr. Mayweather was the heavy favorite, and he did prevail, but Mr. De La Hoya still made it a competitive fight. Mayweather-De La Hoya stood as the highest grossing pay per view fight of all time until Mayweather-Pacquiao surpassed it in 2015.

(Boxing fans may be interested in my earlier article about Shane Mosely and Mr. Mayweather, two of Mr. De La Hoya’s most memorable opponents.)

Pacquiao-De La Hoya

On May 3, 2008, Mr. De La Hoya engaged in a tune-up fight against a game-but-overmatched Steve Forbes, hoping for a rematch with Mr. Mayweather. Those plans were dashed when Mr. Mayweather retired for the first of what would be several times. Instead, Mr. De La Hoya accepted a December 6, 2008 fight with Manny Pacquiao. Although Mr. Pacquiao was recognized by most authorities as the top fighter in boxing in the wake of Mr. Mayweather’s retirement, he was moving up two weight divisions, from 135 to 147 pounds, for the fight with Mr. De La Hoya. Furthermore, Mr. Pacquiao had only fought once at 135, having previously been at 130 for several years. Mr. De La Hoya was the betting favorite.

Mr. Pacquiao’s trainer, Freddie, was quite confident going into the fight. He stated confidently that Mr. De La Hoya, whom Roach had previously trained, could no longer “pull the trigger.” After Mr. Pacquaio battered a seemingly helpless Mr. De La Hoya for eight lopsided rounds, scoring a technical knockout. After the fight was over, Mr. De La Hoya walked over to Mr. Roach and told him that he had been correct.

At age 48, Mr. De La Hoya apparently believes that he has found that which he lost just over 12 years ago.

Before a Comeback From Retirement, Consider Why You Retired

People retire for different reasons. Mr. De La Hoya retired because he could not pull the trigger anymore. Floyd Mayweather “retired” in 2008 for reasons unknown. Whether to comeback from retirement is ultimately a personal decision. However, reality should inform that decision. When considering a comeback, the person pondering the decision should think back to why he or she retired in the first place. I dare say that the reason for the retirement is often relevant to whether a comeback is wise. Let it be said that this is especially relevant in combat sports in which serious injuries are possible.

Astute readers will likely note that I have some questions about whether Mr. De La Hoya’s comeback is a wise idea. When I read the news, I thought back to something that a wise man named Charles Barkley said in 2006 or 2007. The story, as best I remember it, goes as follows.

Wisdom from Charles Barkley

In either 2006 or 2007, there were rumors that the great Scottie Pippen, who had retired from basketball in 2005, was considering a return to the NBA with the Cleveland Cavaliers, which were then led by a young LeBron James. Mr. Pippen was nearly 40, and his last season with the Chicago Bulls had been something of an injury-ridden farewell. He was several years removed from having been an effective player.

Mr. Barkley, a basketball Hall of Fame-inductee like Mr. Pippen, had a bit of an acrimonious playing history with Mr. Pippen that we needn’t rehash in detail here. He weighed in against the rumored comeback idea with wise words that stuck with me. In a sort of open letter to Mr. Pippen on TNT’s Inside the NBA, Mr. Barkley stated, multiple times: “You retired ’cause you can’t play no more.” I think that was the exact quote, but if not, it is close enough.

Wise words from Mr. Barkley. If you retired because you were not good enough to compete anymore, it is unlikely that growing older resolved the underlying issue.

On the Reasons for Mr. De La Hoya’s Retirement and the Prospects For His Return

To be sure, I would not necessarily say that Mr. De La Hoya was bad in 2008 when he lost to Mr. Pacquiao. Mr. Pacquiao was sublime, and he would soon establish himself as the best fighter at 147 pounds against opponents much closer to their primes than Mr. De La Hoya had been. But Mr. De La Hoya saw something in himself in that fight in which he was not competitive which told him it was time to leave the fighting to others.

The number of boxers who lost their ability to pull the trigger in their mid 30s and found it again in their late 40s is small. By “small,” I mean that Mr. De La Hoya would be a club of one.

Final Thoughts

If Mr. De La Hoya does indeed go through with his comeback, I do hope it goes well. He was the most popular fighter in boxing for many years and surely still retains his legions of his fans. In his prime, Mr. De La Hoya had a well-earned reputation for taking on difficult fights that many other fighters of his caliber would have avoided. For there to be any hope that this goes well, he ought to pick his fights with far more discretion than he did at the peak of his powers. Perhaps there are some fellow greats who retired for similar reasons who might be interested in a fight?