Evander Holyfield (left) probably should've retired more than a decade ago. Photo / Mary Ann Owen-FightWireImages.com

Who ever thought we’d see a day when Roy Jones’ record would include seven defeats? Or, perhaps more accurately, and certainly more depressingly, seven defeats and counting?

The news last week that Jones’ fight with Danny Santiago was postponed because of a hand injury does nothing but delay the inevitable. Jones will fight again. And the smart money says he will lose again – probably not against Santiago, but against someone eventually. Jones once was nearly unbeatable. Now he’s beatable even to a fringe contender like Danny Green.

Whether you loved or hated Jones in his prime, you have to feel sad for him now, as he nears his 42nd birthday and still insists on making his living as a professional boxer. For fight fans, this brand of emotional distress is nothing new. With rare exceptions, our pugilistic heroes always hang on longer than we’d like them to.

Maybe once or twice in a generation, a superstar fighter makes a Costanza-like exit: Rocky Marciano. Marvin Hagler. Lennox Lewis. Ricardo Lopez, if you could call him a superstar.

The vast majority hang on far too long. But who says we have to settle for the unhappy endings they give us? Why can’t we re-write the endings so that the fight game’s finest retire at the absolute perfect moment?

What follows is a look at what would have been the perfect note on which to go out for the five biggest stars of Jones’ era: Jones himself, Oscar De La Hoya, Mike Tyson, Evander Holyfield and Julio Cesar Chavez. (Note: George Foreman probably belongs on that list in terms of star power, but you could make a strong case that his second retirement actually was well timed, so I’ve chosen to exclude him from this discussion.)

ROY JONES

This one is easy: Jones’ perfect time to retire was after he beat John Ruiz to claim a heavyweight belt. It would have seemed ludicrous at the time for Jones to quit after one fight at heavyweight and with several options for eight-figure paydays out there. But in hindsight, we know he never fought again at heavyweight anyway, missed out on those eight-figure fights (against the likes of Tyson, Lewis or Holyfield) and hit the wall with maximum force when he tried to cut back down from an all-muscle 193 pounds to 175.

If Jones had quit in ’03 after dominating Ruiz, he would have been 48-1 and would have had a decent case that he belonged in boxing’s all-time pound-for-pound Top Five, near names like Robinson and Armstrong. Sure, detractors would have held his opposition against him, but the case could have at least been made on Jones’ behalf. Not anymore. When the greatest fighters of all-time saw their physical abilities decline, they found other ways to win at least some of their major fights. Who’s the best opponent Jones defeated after his controversial decision victory over Antonio Tarver in ’03? A washed-up, blown-up and rusty Felix Trinidad? The decaying remains of Jeff Lacy? Anthony Hanshaw?

Had Jones quit on top at age 34 after the Ruiz fight, sure, there would have been unanswered questions, but is that such a bad thing? Maybe if Marciano hadn’t retired when he did, he would have lost four of his next six fights and ended up rated on par with Max Baer or Floyd Patterson or Ken Norton, somewhere on the borderline of the all-time heavyweight Top 25. Unanswered questions are sometimes preferable to the answers we end up getting.

OSCAR DE LA HOYA

There are two very different questions to consider here: When would retirement have best served De La Hoya? And when would De La Hoya’s retirement have best served the sport of boxing?

I wrote a column the day after De La Hoya knocked out Ricardo Mayorga, taking the unpopular stance that “The Golden Boy” should retire immediately because he was never going to get another opportunity so perfect, against another opponent who could make him look so sensational, to go out on top. I took heat from some other writers for suggesting that De La Hoya walk away at age 33. But we now know that moment was indeed his last opportunity to go out with people buzzing primarily about his talent.

However, De La Hoya did benefit financially by fighting on, and the sport benefited enormously because he passed the torch of superstardom, to varying to degrees, to Floyd Mayweather and Manny Pacquiao. But this article is about the fighters themselves and what’s best for them. And when all factors are considered, I think De La Hoya retired just one fight too late.

The money he made against Mayweather was well worth any punishment he took, and his reputation wasn’t damaged at all by a razor-close loss to the then pound-for-pound king. If he’d come out after that and announced that his next fight, in the Los Angeles area against Steve Forbes, was a hometown farewell fight, it would have provided the perfect ending. We all know it would have been tough to quit at that point, without Pacquiao having dished out that beating most fighters need in order to be convinced the hourglass is bottom-heavy, but in retrospect, that’s when Oscar should have gotten out.

MIKE TYSON

There’s plenty to chew on here. If Tyson had quit all the way back in 1988, right after destroying Michael Spinks, some would have considered him the greatest heavyweight who ever lived. If he’d retired after the Bruce Seldon fight in ’96 –
fueled by some sort of “I can’t fight in a world without Tupac” sentiment – he’d have been spared most of his lowest moments in the ring. If he’d faded into Bolivian after falling to Lewis in ’02, it would have been a sad but fitting ending and he wouldn’t have had to lose to any ham-and-eggers. And if he’d hung around for exactly one more fight after that, he could have gone out on a high note, with a one-punch KO of Clifford Etienne.

While the first couple of scenarios are perfect from a legacy standpoint, they’re just too absurdly unrealistic. We can all agree Tyson should have quit sometime before losing to Danny Williams and Kevin McBride. But what would have been preferable: ending with the Lewis loss or the Etienne win?

It’s a tough call, but on the off chance he might never have gotten a tattoo on his face, I’ll go with the Lewis loss. From the defeat itself to his seemingly-at-peace postfight interviews and the image of him cradling his baby in the dressing room afterward, it would have been a sweetly poetic ending to a turbulent ride.

EVANDER HOLYFIELD

I got Holyfield on the phone last week and asked him when the perfect time to retire would have been, and he said, “In 2018, after I defeat Wladimir Klitschko to re-unify the heavyweight championship of the world.”

(Note to all those without senses of humor: This is not a real quote. I did not really interview Holyfield last week. Please do not post this quote on your Twitter feeds as some sort of exclusive scoop.)

It’s hard to believe it, but Holyfield is still fighting more than a decade after the perfect time for his retirement. That time was at the end of 1999, after he lost his rematch to Lewis. It was a fight that could have gone either way (I scored it a draw from ringside), which was good news for Holyfield’s reputation since it furthered the belief that he would have beaten Lewis in his prime, having nearly done so on what we assumed were his last legs.

Holyfield did score one impressive win after that, upsetting Hasim Rahman in Atlantic City, N.J., but we can live with that stricken from his record because it was more than compensated for by his six post-Lewis defeats and, most importantly, his trilogy with John Ruiz. For the record, the horror of that trilogy is frequently overstated by those with short memories. The first and second fights were decent and packed some drama; only the third was truly awful. But the three fights launched Ruiz into the heavyweight elite, so in order to erase from existence Ruiz vs. Kirk Johnson and Ruiz vs. Fres Oquendo, Holyfield retiring in ’99 becomes a must for fight fans.

JULIO CESAR CHAVEZ

The great Chavez getting abused by the ordinary Willy Wise remains one of the saddest sights of the last couple of decades in boxing. And the WBC leaving Chavez ranked No. 1 after that so he could get clubbed into submission by a prime Kostya Tszyu remains one of the strongest arguments for the abolition of Jose Sulaiman’s band of merry scumbags.

Even though Chavez was on the decline from his 1993 “draw” against Pernell Whitaker on, he remained a championship-caliber fighter for a few more years and it wouldn’t have been reasonable to expect him to retire after his first official defeat (against Frankie Randall) or his second (against De La Hoya).

The right time probably would have been after defeat No. 3, also against De La Hoya. Chavez got more business done than he did in the first fight with Oscar, made what amounted to a gutsy last stand at age 36, then undid some of the gutsiness by surrendering on his stool after the eighth round. Maybe that wouldn’t have been the perfect image to leave on. But it was the perfect sign that the fight had been beaten out of Chavez and, in hindsight, the perfect way to spare Chavez the humiliating experiences that followed.

RASKIN’S RANTS

ÔÇó A penny’s worth of free public relations advice for boxers: If you’ve ever made a million dollars in a single night, don’t complain about being in a “slave contract.”

ÔÇó A penny’s worth of free public relations advice for ex-boxers-turned-promoters: Just don’t talk to the press. Ever.

ÔÇó Hey, I didn’t fall asleep during ShoBox last Friday night! No, not because the fights were over so quickly; because I fell asleep more than two hours before the show started. A penny’s worth of free advice to rapidly aging semi-narcoleptic boxing writers with little kids who get up at 5 o’clock every morning: Don’t even bother trying.

ÔÇó I did catch ShoBox on my DVR Saturday morning, and that definitely goes down as one of the best cards in the history of the show. I don’t know where a guy with four knockouts in 19 prior fights gets off throwing an uppercut like the one Tim Coleman used to wreck Patrick Lopez, but I’m glad he threw it.

ÔÇó Boxing may be dead this October, but Ring Theory isn’t. Check out a new episode later this week. Who knows, Bill Dettloff and I might even come up with something to talk about.

Eric Raskin can be reached at [email protected]. You can read his articles each month in THE RING magazine and follow him on Twitter @EricRaskin