Evander Holyfield and the 10 Saddest Old Fighters in Boxing History

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Ernest Hemingway warned against anyone becoming close to a boxer. 

After spending close to three years tracking legendary Cuban boxer Guillermo Rigondeaux from Havana to Miami, then Los to Angeles and dipping down to Tijuana when I joined his entourage, a title shot in Dallas then to Dublin, Ireland for his last fight, let me assure you—Hemingway knew what he was talking about.

Inside a boxing ring is where most boxers feel the safest in the world. When they lose the ability to defend themselves inside that squared circle, very often they go on to lose everything outside it. 

Few stories end well in boxing. If you follow a career long enough and your heart stays with the horse you rode in on, the cheque for that meal is on the way, and it's guaranteed to be more than you ever thought. 

It's rare that anything this brutal sport adds to your life it doesn't also take away from it. All the same ingredients that make you fall in love with a boxer and his story threaten to punish you in the end.

But there it is. What's the alternative? 

It's part of the journey we sign on for. We're at risk in boxing in a way we aren't in other sports.

You don't play boxing. And when you find a real connection with a fighter, whatever it is we're all struggling for somehow gets reflected in what our heroes in the ring struggle for.

Their fight becomes yours too. 

For a fight fan, nothing is more gratifying than following a boxer on his rise; all that potential leading him into the imagination like a trail of gasoline responding to a match.

Where was Tyson headed after Spinks? What was Bowe capable of after Holyfield?

Could anyone hope to compete with Roy Jones Jr. from any era when he was in his prime?

Our grandparents might've had Joe Louis or Marciano, our dad had Ali—suddenly we might have someone of our own to brag about.

Then, somewhere along the line, it all changes.

In the Cinderella story that boxing can often be, it's always one punch to midnight for a life that might never be the same... 

10. Tommy Morrison

Tommy Morrison and that juiced-up left hook of his tore through the heavyweight decision. Yet another great white hope was on the scene. Tommy had even been personally selected by Sylvester Stallone to star in Rocky V to basically chart Tyson's rise and fall in a morality play that included Don King and a lot of ripped off Cus D'Amato words of wisdom. 

When Tommy encountered Ray Mercer and met with one of the most vicious series of blows ever delivered in a boxing match, you couldn't help but know that for Morrison everything had changed forever. 

Nobody had any idea how bad things could get for Morrison. Michael Bentt and Lennox Lewis nearly tore Morrison's head off.

Then, when word got out that Morrison had contracted HIV and retired from boxing, it was quickly followed by Morrison denying he had it and announcing his return to boxing.

The deterioration of his career and life only gained momentum. Even to look at current photographs of this man today is a frightening experience in gleaning what he's been through. 

Have a peek at the segment he ran for a new boxing video game recently. Gruesome. 

9. Shannon Briggs

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At one time Shannon Briggs was touted as Brownsville's newest offering for heavyweight champion. 

He'd survived the same streets that gave us Riddick Bowe and Mike Tyson. He had Tyson's former trainer in Teddy Atlas steering the ship. He had all the tools and style ready to make him a major player in boxing. 

Then, on an HBO showcase fight against Darrol Wilson, Brigg's asthma left him tanked and by the third round he was on the canvass with the fight called off. His career was derailed. Or so we thought...

Briggs came back and won his next five fights, including (in my opinion) a gift decision over linear-champion George Foreman.

Now he had Lennox Lewis on his hands. He was a big underdog but he had a chance to dethrone one of the most dominant heavyweights ever.

Then, somehow, he just about did. He hurt Lewis early in the fight and nearly, if he would've landed a solid punch more, finished him.

But it didn't unfold that way and Lewis regrouped.

By the fifth round Shannon Briggs was winning more fans than he had in his entire career just by miraculously getting up off the canvass over and over again. He showed enormous heart and Lewis brutally punished him for it.

Over the last 13 years, Briggs never stopped fighting. His weight ballooned. He was savagely dispatched by Vitali Klitschko and extensively hospitalized.    

Now 40, Shannon fights on toward his dream of reclaiming the world title. It's a hard dream to cheer him on for at this point.

8. Roy Jones Jr.

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Jones had so little personality, such a remarkably classless compulsion to humiliate his opponents throughout his career, that I promised myself from the beginning, no matter what, you are not going to feel sorry for this man when somebody catches up to him. 

He deserved what was coming to him. Of course he worked hard, but God gave him that tool kit to work with. And, for better or worse, boxing is a lot like relationships: you might have everything on paper, but it doesn't mean you necessarily have any chemistry. 

Jones never connected with an opponent in any meaningful way in any of his victories. He never found a serious fan base that remotely reflected his prominence atop the sport. He had the charisma of a stepping stool whenever he opened his mouth.  

But no fighter ever brought more ability into a ring than Roy Jones Jr. Forget Floyd or Tyson in terms of dominance. Roy Jones Jr. had gears all his own that we've never seen before or since.

Nobody was ever able to dominate at such a high level for so long.

Nobody's career pisses me off more. 

His combination of breathtaking speed, flawless timing and reflexes, power in both hands, blinding footwork, meticulous preparation––Roy had it all so long as nobody could come close to hitting him. He won a heavyweight title from John "The Quiet Man" (worst moniker of all time) Ruiz, the most boring fighter ever to lace up gloves.

Roy relished his fame and had created a legacy of humiliating each and every opponent wherever possible.

I was in awe but reaffirmed the pledge: never feel sorry for this man. 

Then somebody named Antonio Tarver came along and hit him. Roy finally had some chemistry for the first time with an opponent. He narrowly escaped the fight with a win. Plenty of excuses for the performance. 

They had a rematch and Roy Jones Jr. was on the other end of the greatest few seconds before a fight in history:

"You got any questions?" the referee asked asked both fighters.

"I got a question," Tarver glared at Roy. "You got any escuses tonight Roy?"

What was even more amazing on my end, I'd just watched a DVD Roy had put out with his strength and conditioning coach that was the most laughable fluff job I'd ever seen. Roy was an F-16. One person after another lined up to say how Roy had an off night but was the greatest thing since sliced bread and was going to annihilate Tarver. 

A straight-left hand from Tarver put out the lights on DVD sales and Roy Jones Jr.'s career.

But he kept fighting. And fighting. And getting knocked cold. Yet he couldn't stop. Knocked out again in Russia. There was again spookily unconscious while, at the same time, reaffirming his desire to continue.

Don't feel sorry this man.

But you had to.

And I did. 

I resent him even more now.

Is Jones Jr.'s career the ghost of Christmas future for Floyd Mayweather? We'll have to find out. 

7. Muhammad Ali

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I've listed 10 of the saddest cases in boxing, but what's the criterion? 

Is lost potential with a career cut short more tragic than watching a comatose Ali get pummeled by Holmes or Berbick?

Ali had the life he wanted.

Ali scared us in most of his big fights.  

How many times was Tyson ever an underdog? Once? Twice?

F. Scott Fitzgerald said there are no second acts in American lives.

Really? 

Every major fight of Ali's career amounted to an act. Both Listons, Patterson, Foreman, Norton, Spinks, Holmes, you name it. 

Put it this way: Ali fighting a nobody gave Stallone a script for an Oscar winning film with a second-rate former CFL running back playing Ali's role in the film (don't get me wrong, Apollo Crede is dope).

Ali is the greatest drug boxing ever produced. He's ruined athletes ever since. Now they all have to pretend they have anything close to Ali's personality and flare. Nobody will.

Ali said it best, "There are no jokes. The truth is the funniest joke of all."

Who's life or career can touch Ali's for drama? Even now... 

6. Oscar De La Hoya

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First the bitter loss to Trinidad after Oscar's no-hands-look-at-me-dad joyride on his bicycle in the last few rounds. 

The next loss comes when Mosley takes home a split-decision over him.

In the rematch Mosley defeats De La Hoya again. 

Next, Bernard Hopkins overwhelms him with one perfectly placed body shot. 

The biggest pay-per-view of all time and Oscar De La Hoya comes up short yet again against Floyd Mayweather Jr. 

Finally, the coda to Oscar's career comes when he quits on his stool against Manny Pacquiao after being dominated in every conceivable fashion save vocal ability.

Oscar's career is unique. Tremendous success as an amateur and a professional. Unprecedented marketability. He took all the big fights he could during his time. Over the course of his boxing career, Oscar might have one of the most impressive trophy cases ever assembled. He has all the spoils any boxer could ever want from a career. Yet...

Oscar's career is defined by the fights he came up short.

It began with Trinidad, a particularly nasty career defining fight, because Oscar gave it away. He was twice the fighter Trinidad was on that night and Oscar coasted.  

Now he's entering rehab. He's not even 40. There are demons from his career that aren't going anywhere. And having come so close on so many occasions, in many ways, makes those demons even more of a tragic burden to carry.  

5. Arturo Gatti

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I don't even want to go near his suicide/murder. It's too awful. We don't need to touch on any of that horrible mess to establish Gatti's saddest boxer credentials.  

Gatti's epic legacy was earned in a ring.

When you talk to fighters there's always a special place for Arturo Gatti.

I've met several fight fans, myself included, where the only fighter we've ever cried for was him.

That man's face in agony was the kind of thing Michelangelo would get pointers from.

It's a bad idea to watch anybody else on the same night you watch over one of Gatti's fights. Gatti's a simple guy, but he has a way of creating a symphony in the ring whereas most give you a few notes here and there.

I hated him for all the reasons I loved him. He was fighting as if he'd already died. Where did it come from? 

There was so much darkness waiting to claim him (was anybody surprised to hear he'd died young?), yet nobody could turn us all into flammable material easier, or burning hotter, than Arturo Gatti. 

He's the fighter more than any other that boxers envy as representing the best of the sport. But that same violent beauty cost him an extraordinary amount inside and outside the ring.  

4. Joe Louis

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One of the saddest things you could say about Joe Louis is that Rocky Marciano's last blow, sending him helplessly through the ropes, is the brightest ending we have of Joe Louis's life.  

Along with all those debts to the IRS, his life dragged on, weighed down even further by addiction and soul-shatteringly sad jobs like working as a greeter outside a casino in Vegas. To hear accounts of seeing him near the end of life, usually sporting a cowboy hat, is miserable.  

It was said of Joe Louis, when he fought Max Schmeling, that he was the first black man white America cared about. Finally they could see themselves reflected in what Louis stood for as an American champion taking on Hitler's champion.  

Joe Louis far outlived his legend. When he was flush, he shared everything he had. He achieved a degree of elegance in the ring few if anyone could match. He was a heavyweight champion to the world when it meant something extraordinary. 

But his debts caught up with him and the only way to have any hope bringing a pay cheque was to keep fighting well past his prime.

Then he entered the fray of wrestling...

Pretty soon a cigarette was dangling over his bottom lip and he was a has-been sitting in the front row at Vegas fights. There's video of him very shortly before he died, wheelchair bound and barely present, attending a fight. It's one of the saddest sights in the history of boxing given the heights he achieved not just for boxing, but for what the best of America stood for.  

3. Mike Tyson

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As with Louis, Tyson was a huge earner who blew through money until it forced him to continue far too long. Some estimates have him making and losing well over $400 million. He declared bankruptcy shortly after his career was ended by someone named Kevin McBride. 

Tyson reached his peak against Spinks and not only never improved beyond the age of 22, his skills and focus rapidly declined.

He got into bed with Don King. He went from being the world's most marketable athlete (Nintendo, Toyota, Kodak, Pepsi, NYPD ads) capable of being a billionaire by the end of his career to a convicted rapist at 25, followed by a series of sideshow outbursts and deplorable behavior in and out of the ring.

Nobody captivated the sport the same way Mike Tyson did. There might not have been a bigger celebrity in the world during Tyson's heyday. When he traveled to foreign countries kings and presidents sought to meet with him. 

Yet Tyson will always be remembered for the promise he squandered. Already his brilliance in the ring has been cast into doubt by the legacy he shaped after Spinks. 

Few credit Tyson with what must be his greatest achievement, marketing himself to the American public better than any entertainer despite the enormity of his decline. We could never take our eyes of him in the ring or in our imagination and he remained and remains relevant to our daily life an incredible 26 years after he turned professional as a boxer.

But we lost the career that might have been. What was the Tyson who fought Michael Spinks capable of against the best from his era? How would he have fared against Bowe, Lewis, Mercer, Holyfield, the Klitschkos, George Foreman, David Tua? We got very little of what was there to be had.

Tyson vs Lewis had the air of a public execution.

His audience was willing to pay huge money to get blood and of course label him as the one who should be locked up. For $25 million Tyson gave it to them. 

I asked Ronnie Shields once if he knew at the outset of training Tyson for that fight whether or not he was shot. His look said it all. "No doubt."

But there will still more bills to pay.

So Tyson was left with the stepping-stone fights toward huge money with nobodies like Danny Williams and McBride.

Both fights amount to as depressing an end to a career as you can find.   

2. George Chuvalo

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George Chuvalo fought for 20 years.

When the documentary Facing Ali was released recently, he was notably one of the boxers speaking English without subtitles assisting the viewer in understanding him. 

If you watched one of his fights and went out on a limb and said he was the toughest, most iron-chinned boxer who ever lived, few in the world of boxing would argue.

And that's just discussing his toughness in the ring. Over the course of a career that included Muhammad Ali (twice), Jimmy Ellis, George Foreman, Jerry Quarry, Joe Frazier, Oscar Bonavena, Ernie Terrell, and Floyd Patterson, nobody ever dropped him.

But of the 18 losses in George Chuvalo's career, none say anything about the real losses in his life that did the damage.

Chuvalo lost three sons to suicide. After his second son died, his wife committed suicide.

In retirement, George Chuvalo has spent many years touring schools with his new wife, speaking on the devastation of drug use to teens.

1. Evander Holyfield

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Evander Holyfield continues to fight at the age of 87. He has more children than most pharaohs were able to sire. Despite Evan Fields living at the same address as Evander and sharing the same phone number, please don't assume all the heavy duty shipments of HGH and steroids meant for delivery there have anything to do with Evander's career. Evander would never cheat (except on his wives, over and over and over again). Have trust that Evander's God will find that Evan Fields and redirect his life toward a path of the most mind-numbingly self-serving, vainglorious, slurring pronouncements ever delivered post-fight.

Evander Holyfield might be the biggest overachiever in the history of the sport. He took on far too many battles that, from the outset, seemed hopelessly reckless. He won his fair share too. But the punishment he sustained along the way was staggering. What those wars took out of him will continue to unfold.

In 2005 the New York State Athletic Commission banned Holyfield from boxing due to "diminishing skills" making the risks to his health far too great for him to continue to compete.

That was back when Holyfield was a spritely, roided-out 81 years of age. MC Hammer's long association with the boxer still managed to leave a spring to his step.

Now at 87, forced to dye even the hairs of his awful mustache, Holyfield continues to move forward with his career on God's behalf attempting to satisfy his ample child support demands.

Despite loathing everything to do with Holyfield (except his 1992 Sega videogame, where I knocked his ass out repeatedly), I felt the worst for him when James Toney destroyed him.

Toney beat him back in 2003. A body shot dropped the valiant 79 year old and his corner soon through in the towel in the ninth round.

Watching Holyfield step into the ring at 87, broke, a mountain of bills, ever-ready to slur his way toward Jesus, few have ever seemed more pathetic. And for all this man accomplished with his career, to be reduced to a cheap punchline is remarkably unfortunate. Even worse, that giant heart and stubborn determination that got him so far in life, were exactly the ingredients that brought him down. He never knew when to quit (or put on a condom).