BIZARRE things can happen when a boxer enters the twilight of a career. Their bodies soften. Their talents fade. They attempt to time-travel, and in an ironic way they succeed, for they find themselves stuck in the past. They once felt immortal, and in a grotesque way they now are, for they are repeatedly reanimated, not by mad scientists but by money-hungry promoters. Exotic realms are charted as they roam this limbo; places they never dreamed of visiting when Las Vegas and London would welcome them. Carnivals pay them to degrade themselves in gimmick matches. Siren songs lure them with promises of money and a return to lost glories, and then they are devoured by younger impostors.

These are not the tales of the boxers – almost all boxers – who fight on for too long. These are the tales of the boxers who fight on for years and years after they were last even remotely viable as contenders. These are tales of oddities, of embarrassments, of unusual locations – with no happy endings in sight.


A legendary warrior who has already featured in several tales of the unexpected is called up one last time to perform in front of an audience of ghouls – with the once-most powerful man on the planet at the top table.

Even in his prime, Holyfield had experienced plenty of fantastical and supernatural twists and turns. He repelled time-travelling challengers from another generation, he watched a man fly into a ring as he fought, he employed a faith healer after supposedly suffering a heart attack in the middle of a boxing match, and he survived an attack by a cannibal.

But as he approaches the Twilight Zone, the ‘Real Deal’ starts to look less convincing. Defeats and hiatuses are blamed on injuries, but he refuses to concede the injuries may themselves be a result of ageing. He promises “the best is yet to come” as he launches a comeback in 2006, aged 43.

He beats some hand-picked foes, including a WWE wrestler with some phantom punches, and regains enough momentum to secure two more title shots, travelling to Russia and Switzerland where, in the shadow of the Alps, at 46, only Three Blind Mice prevent him from beating a 7ft Beast From the East. Undeterred, Holyfield performs a sleight of hand to earn the distinction of becoming the sport’s first “five-time” heavyweight champion. He shoots down a White Buffalo on its last legs and picks up the WBF title. In reality the belt means nothing, but fans and media parrot the line. He then ends his career – officially, anyway – with a win in Denmark against an inappropriately named boxer called Super Brian in a fight featuring combatants with a combined aged of 94.

But in case Holyfield isn’t yet old enough, and his story not strange enough, it concludes more than a decade later in truly farcical circumstances. In 2021, at 58, he steps in at less than a week’s notice to replace Oscar De La Hoya (yes, really) in an exhibition match against MMA star Vitor Belfort.

In the ghastly main event of what is an odious freakshow from start to finish, Holyfield is wiped out in one horrible round. There are stranger things still, as the whole thing is presided over – and commentated on – by that renowned sports pundit Donald Trump. Who better than this uber patriot when the event is staged on September 11? The Don’s involvement is one of the main marketing points of the farce, but in being paid $2.5million just to do what he usually does for free – bloviate to an audience – he is a significant contributor its financial failure.


Fans and pundits alike wonder if they’ve just witnessed the greatest boxer to ever exist, as a former middleweight wins the WBA heavyweight championship. They call him ‘Superman’, and it doesn’t sound like a comic book story.

But a jealous entity called Father Time starts slipping this Superman increasingly potent doses of Kryptonite. After his 2003 heavyweight nadir, Jones physically shrinks and visibly struggles. Then, in a plot twist almost too far-fetched to believe, he loses.

More incredibly still, he loses again. And again. He rallies the ghosts of the past and stages one last charge at a championship, but is burned by a Welsh dragon. By 2009, Superman’s mortality is confirmed once and for all when he travels Down Under and is mown down by a Green Machine in two minutes.

Now in his 40s, he fights on – 18 more times. Even at this advanced age, he becomes the greatest UBO Intercontinental champion of all time. Jones goes on the road, unknowingly carrying that Kryptonite with him. He boxes in Poland, Latvia and repeatedly in Russia, where in 2015 he befriends Vladimir Putin and is given a passport.

The newly dual citizen returns to America, where his career takes a turn for the (even more) bizarre. First, he fights a fan – a man who’d never boxed but won a prize draw to box Jones. He then beats a bareknuckle brawler (wearing gloves). And, in a Covid-era empty arena at the age of 51, he obviously play-fights with Mike Tyson in an exhibition so lucrative that middle-aged icons are still staging them to this day.

Jones’s last official match comes at the age of 54 as he mimics Holyfield by losing to a mixed martial artist. The man who beats him, Anthony Pettis, is incredibly not the first boxing debutant to beat a former world champion (more on that in a later episode). But unlike Holyfield, his last appearance results in a ‘victory’, as he beats a celebrity bodybuilder in a so-called ‘metaverse’ exhibition match which renders the real action into CGI so bad it looks like a PlayStation 1 game. In that sense, Superman turns back time by erasing the wrinkles – but unfortunately not that stubborn Kryptonite.


Always possessed of a petulant streak, Holmes issues an ultimatum unlikely to galvanise anyone: at 46 years of age, he won’t box again unless it’s for a world title. And yet, his arm proves unsurprisingly easy to twist when his challenge is answered by a champion of sorts. Brian Nielsen, an unremarkable boxer with a big following in Denmark, offers Holmes a shot at his IBO belt. It’s nobody else’s idea of a “world championship”, but it’s enough to satisfy the easily tempted Holmes.

Nielsen beats Holmes and, not for the first time, Holmes cries robbery. He repeats his title-fight conditions for fighting on, but a problem for a man who probably wants his bluff called is that the loss to Nielsen punts him well out of any recognised set of world rankings.

As time passes and the heavyweight division’s true monarchs somehow resist the temptation to box Holmes, he edges closer to his dotage. He joins a community for the athletically elderly, populated by like-minded old pugs. In its grounds they find the equivalent of a pool filled with restorative waters – a chance to regain their collective youth, to perform again on pay-per-view and, yes, to fight for a championship.

Holmes gathers his friends – 46-year-old Bonecrusher Smith, Billy Costello (43), Tim Witherspoon (41), Greg Page (39) and Juan LaPorte (39). At 49, he is the oldest and most experienced of them all, and he assumes his position as leader of a cult he calls Legends of Boxing. He outlines his vision: “If they won’t let us old guys fight for world titles, we’ll just make our own.”

And so, cocooned in his delusion, with the support of his acolytes, Holmes launches the Legends of Boxing Championship, open to boxers aged 35 to 55. In June 1999, Holmes stops Smith for the inaugural heavyweight belt, with Page beating Witherspoon in an “eliminator” and Costello taking the middleweight honours with a win over LaPorte.

Holmes enters his 50s as a champion once more and even defends his new status, again beating a younger man in Mike Weaver, 49. On the undercard, the world’s shortest giant – a 5ft 11lbs, 350lbs carnival act called Butterbean – is held to a draw by a boxer who’s won barely half his fights. Shockingly, the Legends of Boxing series is a commercial flop, but Holmes can’t resist one last fight, against the aforementioned Butterbean. In July 2002, he concedes 16 years and 80lbs but wins – albeit after a last-round scare that is finally enough to convince Holmes, at 52, to quit. Not even science fiction or fabricated belts can conjure up another payday.


‘Neon Leon’ is restless. It’s 1991 and he hasn’t boxed for four years. There was a time when he was good enough – and young enough – to win an Olympic gold medal and later the heavyweight championship of the world, beating none other than Muhammad Ali.

Spinks has won only one of his previous 10 contests and is now in his late 30s, but he watches as an older, fatter, balder man rides a comeback all the way to a title shot – and millions of dollars. Dollars that Spinks desperately needs. “If Big George can do it, so can I,” he tells himself.

The comeback begins in standard fashion; the past-it big name beating a series of unknowns. But something strange starts to happen to Spinks: he develops a split personality. One half of him is the familiar face with the fading talents. The other half is unleashed whenever he crosses the Pacific, landing in the Orient with new powers in a new sport.

This two-headed Spinks is separated by geography but co-exists in time. In the backwater boxing rings of his United States homeland, he is struggling. He is held to split decisions by fighters with records reading 6-17-2 and 8-28. But he goes back and forth to Japan, where his alter-ego as a wrestler battles big names in big arenas – and even wins a world title.

On March 25, 1992 – just five days after winning a 10-round boxing match in Missouri – Spinks beats a certain Tarzan Goto for the Frontier Martial Arts Wrestling (FMW) heavyweight championship. He is now the first man since Primo Carnera to win major titles in both boxing and wrestling.

The wrestling reign lasts barely two months, and fits nicely between bouts three and four of his boxing comeback. He loses the FMW belt in a cage match and grapples for another year, but his boxing Hyde regains control from his wrestling Jekyll. Truth be told, more potent demons – those of a more intoxicating, addictive nature – prove more powerful than both.

Boxing serves as a quicker and easier way to pay for his vices. Pretensions of a comeback become a secondary motivation and are exposed in a defeat to a 13-8-2 fighter. There’s a further loss to a 2-34-1 journeyman and a 69-second knockout to a man who’s never even boxed before. Once upon a time, Spinks set the record for winning a world heavyweight title in the fewest fights (eight). Now, he suffers the ignominy of being the only former world champion to lose to a debutant (a status that remains until Roy Jones vs Pettis 29 years later).

Spinks ends his boxing career with the lowest winning percentage of any heavyweight champion, at 56.5% (26-17-3). It’s a sad summary for a man who once beat boxing’s Greatest Of All Time – but at least he can say he also beat Tarzan in Tokyo. Not even Ali could claim that.


“Roll up! Roll up! Come see the man who knocked out Mike Tyson!”

Dodgy promoters and ringmasters repeat the call as the travelling circus that is the late stage of Danny Williams’ career continues to tour, primarily around Eastern Europe, almost 20 years after the advertised selling point.

In 2004, likeable Londoner exorcises the ghost of Mike Tyson and believes it is a gift. For a while it is, as it gives him money, fame and opportunity. But it soon turns to a curse; one that pursues him relentlessly for decades as Williams traverses a fistic purgatory, dragging with him this millstone masquerading as a marketing tool.

As he ages, his form dips. The wins are harder to come by and the defeats grow more emphatic. In a time so long ago that Derek Chisora is still a prospect, ‘Del Boy’ thrashes Williams. It’s a spectacle so sad that the British Boxing Board of Control will never again license Williams.

But Williams fights on, leaving the land that has forsaken him. He is still, after all, “the man who knocked out Tyson”. Nobody will let him forget it. Again and again, he is paraded in front of ever-diminishing crowds.

Along the way, Williams travels to 16 countries, boxing more than 40 times, some of them not even official bouts. He makes it back to the UK in 2018 at the age of 45 thanks to BIBA, the alternative licensing body that sanctions his gimmick match with a former lightweight (he loses). On a happier day, he is crowned “world heavyweight champion” by an outfit called the GBC when he knocks out a man with 42 defeats from 45 contests. He also fights for the Latvian championship, despite being British and facing a Russian.

There are glimpses of his old form. Williams stops 24-0 Boban Filipovic. He gives Oleg Maskaev and Mahmoud Charr good fights. But these are outweighed by the embarrassments. He loses not only to the lightweight but also to journeymen, to debutants, to a 53-year-old, and to one obscure opponent in just 23 seconds.

This double-length episode ends on a cliffhanger. Williams has just lost again – for the 25th time since Chisora – in front of about a dozen people in an Estonian gymnasium. He’s now 50 years old, but this is as recently as August 2023. We know better than to expect we’ve seen the last of him. Will he or won’t he fight again? Stay tuned… this is, after all, “the man who knocked out Mike Tyson”.

*IN SEASON 2: Will the man who knocked out Mike Tyson box on? What will happen when Tyson himself re-enters the Twilight Zone and fights a YouTuber? Is Manny Pacquaio about to join the cast? And has Floyd Mayweather’s exhibition tour finally fizzled out? Stay tuned!