Thirty five years ago (on January 22, 1988), Mike Tyson defended his undisputed heavyweight championship with a fourth-round stoppage of Larry Holmes at the Convention Center in Atlantic City, New Jersey. The 38-year-old former champ challenged the undefeated peak-form Tyson after nearly two years out of the ring and clearly wasn’t ready for the “Baddest Man On The Planet.” However, Holmes would make an extended comeback in his 40s.

This story by award-winning author Don Stradley chronicles the final world title campaigns by the all-time great. The article was originally published in the Larry Holmes special (the May 2022 issue), which is available for purchase at the Ring Shop.

A LOSS TO MIKE TYSON SEEMED LIKE THE END OF THE STORY, BUT HOLMES WOULD RETURN AFTER A THREE-YEAR BREAK TO BEGIN THE FINAL CHAPTER OF HIS CAREER

When he fell for the third time that night in Atlantic City, Larry Holmes was done. 

Mike Tyson had scored a fourth-round stoppage. If the sight of Holmes on the canvas wasn’t a clear enough message for the audience, there was referee Joe Cortez swooping in to wave the contest off. The ending had been dramatic, the gallant Holmes trying to withstand a younger man’s speed and power, trying to summon the old magic one last time.

Holmes wound up on his back, yelling at his corner men to come help him up. 

A 38-year-old, ring-rusty Holmes was outgunned by the savagery of Mike Tyson in their 1988 clash. (Photo by Focus on Sport/Getty Images)

Later on, Holmes mentioned the loss in a memoir co-written with journalist Phil Berger. He admitted he had taken the contest on short notice and was in no way ready to face a youthful beast such as Tyson. Holmes actually considered canceling the bout: 

“As I neared the ring, I had this weird thought: Why not be the first fighter to refuse to go into the ring? All those people watching on HBO, I’ll amaze all of them. I’ll tell the announcer, ‘I swear I’ll fight Tyson next month, right after I have a tune-up. Just not tonight.’” 

(Photo by Andrew D. Bernstein/Getty Images)

Of course, Holmes put aside his unease and gave Tyson a few good rounds. At times he even appeared to be controlling the pace and tone of the fight. But once the bombs started landing in the vicinity of his head and chin, the reality of the situation was visible to all.

 In the past, Holmes had been able to shake off the effects of punches. Not now, though. It was 1988 and he was pushing 40. He’d come back for the money being offered, a cool $3 million or so. He had plans to buy up some real estate, and there was no quicker way to make a big wad of money than by fighting Tyson. But Tyson did what young champions are supposed to do. He took the fight to the older man and overwhelmed him.

There wasn’t a writer at ringside not reaching back for references and comparisons. They couldn’t wait to link this bout to Holmes’ own treatment of Muhammad Ali back in 1980, or Rocky Marciano’s dismantling of Joe Louis a few decades before that. A younger, faster lion always displaces the old lion. That’s the law of the jungle, and the law of boxing. 

“I hated the way I lost against Spinks,” Holmes had said earlier in the week. “Win 48 and then lose two like that. That’s why I came back. One way or the other, this time I will retire at peace with myself, and with honor.”

But despite the apparent finality of his loss to Tyson, Holmes wasn’t really done. Tyson had merely retired the first version of Holmes. In three years, a different Holmes would emerge, a grizzled character with enough savvy to beat most of the competition being offered. Holmes’ eventual return to boxing didn’t make as many headlines as the comeback of George Foreman at roughly the same time period, but it was remarkable in its own way. In fact, it was one of the longest and most fascinating comebacks in the history of the business.

Feb. 7, 1992, Atlantic City
Ray Mercer

Fans feared for Holmes’ safety when he signed to fight Mercer. Though Mercer wasn’t precisely in Tyson’s league, he was a young powerhouse on his way to a title shot against reigning champion Evander Holyfield. Holmes was being used as a kind of marketing tool, a way for Mercer to add a famous name to his resume.

By the time it was over, Holmes had earned a unanimous 12-round decision by scores of 117-112, 117-111 and 115-113. This was not just a great moment in Holmes’ later years but one of his best performances, period.

The Convention Center crowd had jeered Holmes as he entered the ring, for he seemed just another greedy old boxer going for the quick money grab. Indeed, he seemed clumsy in the first round, knocked unsteady by one of Mercer’s punches. 

Holmes’ ring craft and cunning bewildered hot-favorite Ray Mercer.

“He scared the heck out of me,” Holmes told the United Press. “He caught me off-balance, he hit me and he hurt me. But the oldness in me said, ‘No, you ain’t gonna fall.’” 

The 42-year-old needed a few rounds to find his rhythm and start boxing. The old jab was still there, and if the old right hand was no longer a lightning bolt, it was still good enough to score points. By the middle rounds, Holmes was consistently beating Mercer to the punch. As Holmes ruined Mercer’s plans, the customers began cheering for him; they knew they were seeing something special. 

At times Holmes even taunted Mercer, luring him in only to potshot him with a quick right. When he needed a breather he’d lay on the ropes, timing Mercer with sharp counters. By the fight’s end, Mercer was bleeding from the nose, reconciled to defeat. Holmes had thoroughly outclassed him.

The surprising outcome can’t really be appreciated today, but at the time, Mercer was a terror. In beating him, Holmes rejuvenated his career. Later on, it was revealed that Holmes had suffered a detached retina before the bout and was fighting with the handicap of partial vision. But nothing deterred him, not his eye and not Mercer.  

“It’s like a new day,” Holmes said at the post-fight press conference. He assured reporters that he was about to go to his hotel room and “cry like hell.”

via coachstrout’s classic fights on YouTube:

June 19, 1992, Las Vegas
Evander Holyfield

The title shot that would’ve been Mercer’s was granted to Holmes. The fight attracted a lot of cynicism, what with the aging Holmes competing for the title again, but he entered the contest as a sentimental favorite and was wily enough to go the 12-round distance without getting hurt. Unfortunately, Holyfield beat him by scores of 116-112 (twice) and 117-111. 

The fight wasn’t especially action-packed, but connoisseurs of boxing might’ve appreciated Holmes’ exhibition of sheer guile. The New York Times described Holmes as something like a “junkball pitcher, using his art to keep Holyfield constantly off-balance and unable to dig his heels in and turn the match into the brawl he wanted.”

Holmes may have been an old junkballer, but he could still let the fastball rip. He landed some punches squarely on Holyfield’s jaw, snapped his head back a few times with uppercuts and occasionally connected with a vintage Larry Holmes left-right combination. At one point, he even took a moment to mock Holyfield’s trainer, Lou Duva. He appeared to fade in the later part of the bout, though fans chanted “Larry! Larry!” He didn’t win the championship, but Holmes certainly won the crowd. If nothing else, Holmes was the first opponent to ever cut Holyfield. 

At 42, Holmes was at that time the second-oldest fighter to challenge for a title, only four months younger than Archie Moore had been when he’d challenged heavyweight champion Floyd Patterson in 1956. But what Holmes had in experience and cunning, he lacked in mobility. Hence, he was forced to do a lot of mauling and wrestling, which had never been his forte. A younger Holmes with more spring in his legs would’ve given Holyfield a much different fight.

Holmes complimented Holyfield as “a great champion and a tough fighter” and took home $7 million for his trouble. Asked if he would’ve done anything differently, Holmes was succinct.

“I would’ve fought him in 1980.”

April 8, 1995, Las Vegas
Oliver McCall

The problem with the second part of Holmes’ career was that he was still capable of beating a lot of opponents but struggled against the top-level fighters. In 1995, at age 45, he lost a close but unanimous decision to WBC titleholder Oliver McCall by scores of 114-113, 115-114 and 115-112. 

“Larry Holmes came to fight; he fought his heart out,” McCall said afterward. 

For the first six rounds, Holmes appeared to be on his way to scoring an upset. He did so well that promoter Don King was heard bellowing to McCall after the sixth, “You’d better not blow this fight, brother!”  

Read “Best I Faced: Oliver McCall” by Anson Wainwright

McCall, a strong but erratic character, needed a big finish to salvage the bout and retain the title. 

Sporting a gash on his cheek, a tired Holmes announced his retirement after the bout. “This is a good fight for me to go out on,” he said.

He was back five months later to win a 10-round unanimous decision over Ed Donaldson at Casino Magic in St. Louis. He’d nearly knocked Donaldson out in the ninth, proving he still had something left.

Jan. 24, 1997, Copenhagen
Brian Nielsen

Victories over Donaldson, Curtis Shepard, Quinn Navarre and Anthony Willis landed the 47-year-old Holmes in Denmark to face that country’s most popular fighter, Brian Nielsen. Fighting outside of America for one of the rare times in his career, Holmes did well. The United Press reported that he put on “a faultless display of relaxed boxing” and had Nielsen “in a bruised and weary state when the final bell sounded.” Yet when the scorecards were turned in, he had lost by a split decision. 

“Why do they do this to me?” Holmes said. “I’m a nice guy.”

Nielsen was a ponderous, uninspired fighter, but he’d been a silver medalist at the 1992 Olympics and now possessed the lightly regarded IBO heavyweight title belt as well as backing from a major right-wing political organization. Despite his high profile, though, his fights were occasionally surrounded by an unbearable stench. Other American opponents who had traveled to Denmark complained of questionable scorecards, bribe offers, and even being drugged before facing Nielsen. The unpopular decision over Holmes added to Nielsen’s dubious mystique. 

Holmes was still serving the same purpose he had served for Tyson, Mercer, McCall and others; he was a name, and not expected to win. Yet he bloodied Nielsen’s nose and did enough to convince one judge (and many onlookers) that he deserved the victory. 

After the bout, Holmes claimed that someone had tried to poison him in a restaurant, and that teenage prostitutes had been sent to his hotel room. Though he threatened to have the bout investigated, he took the loss with more good cheer than usual. “I knew he’d never hurt me and I just wanted to feather my nest some more,” he said.

There were two themes during Holmes’ extended late career run. On one hand, he was blunt about his reasons for fighting: It was the best way he knew to make money, and he looked at it as a sort of well-paying pastime. “I like fighting for money,” he said. “Some people golf. This is my hobby.”

But there was an underlying reason for his continued comeback. He’d always felt underappreciated by fans and the media, and now, more often than not, he was hearing cheers. The pressure was off, too. He was no longer the man who had usurped the more popular Ali. Now Holmes was, in his own words, an overweight grandpa just trying to earn some cash. For the first time in his long career, he was having fun. 

via Boxing Legends on YouTube:

And a few opponents remained. 

First, he squeaked by Maurice Harris, winning a split decision in New York. Then he revisited a couple of his former rivals, “Bonecrusher” Smith and Mike Weaver, in Southern locales. Those two bouts weren’t pretty, but Holmes won both by knockout. 

Then it was time for Larry’s farewell. He had hoped for a big payday against Foreman but settled for the man known as “Butterbean.”

July 27, 2002, Norfolk, Va.
Eric “Butterbean” Esch

Some were disappointed that Holmes, at 52, finished out his career against the comical Eric Esch. Holmes did just enough to win a unanimous 10-round decision, but aside from a moment in the final round when he stumbled to the canvas, the bout was forgettable.

The infamous “Butterbean”

Esch, the 330-pound so-called “King of the Four-Rounders,” did little more than stand in front of Holmes and take punches to his bulbous head. The only drama was in wondering if Esch might get lucky and land one of his winging punches. Esch may have been a novelty act, but he was a strong man and could hurt you. Still, even at 52, Holmes was too smart to get caught by such a crude slugger as Esch. 

For some, it was nice to see Holmes one last time. For others, it was an embarrassing night for boxing. 

Was it a sideshow? Indeed it was, but for Holmes that was part of the point.

“I’ve made a lot of people a lot of money in my 33 years of boxing,” he said. “Don King, Bob Arum and other promoters benefited from me. But these guys didn’t have the guts to send me off properly in my last fight.”

With no one offering Holmes the red carpet treatment, he agreed to fight Esch for $250,000 in Norfolk, Virginia. Novice promoter Daryl DeCroix even arranged to get the fight on pay-per-view. 

Prior to the bout, which was attended by just short of 8,000 people, Holmes was his old irascible self, complaining that he was overlooked and disrespected by the boxing world. It was the same old song he’d been singing for years. 

After the bout, Holmes teased that he might come back for someone easier than Butterbean, but he was joking. He knew the end had finally arrived. There’d been some cheering for Holmes during the bout, but there was also booing. If he’d been dreaming of the day when he’d be fully appreciated, this wouldn’t be it. And though he won easily, smashing his old hands against Butterbean’s concrete skull for 10 rounds probably wasn’t much fun. 

via Roger Russell on YouTube:

But who would’ve imagined that after the loss to Tyson he would continue boxing for another 14 years? Holmes’ record during this second leg of his career was 21-3. For some fighters, that would be a career in itself. For Holmes, it was just a prolonged victory lap. 

It was no surprise that Holmes announced his retirement again. This time he meant it. Butterbean would be the last man he punched for money.

“The fat lady is singing,” Holmes said. “I’m out.”