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Lovely guy…. psychopath’: Unmasking reluctant UFC superstar Jack Della Maddalena

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Lovely guy…. psychopath’: Unmasking reluctant UFC superstar Jack Della Maddalena
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OK, so nobody wants this yarn written less than Jack Della Maddalena.

But that’s fine.

“Because sometimes,” his older brother Josh will insist, “a story needs telling”.

Like, say, how baby bro came into this world amid all the chaos that is having your nose and lip attached. Or within hours, being rushed to a blood transfusion, then surgeries, plural.

“So born hard,” Josh says, “and always fighting”.

But always talking?

Um, not so much.

UFC 322: Della Maddalena vs Makhachev | SUN 16 NOV 2PM AEDT | Australia’s own Jack Della Maddalena puts his welterweight title on the line against Pound for Pound great and former lightweight champ Islam Makhachev in a blockbuster night of fights, live from New York City. | Order Now with Main Event on Kayo Sports.

“Oh, if Jack could fight without ever saying a word,” his longtime manager Tim Simpson says, “he would.”

Which is why even after winning his way to the UFC welterweight title in May, announcing his name, shocking the world, shaking the sport, this newest of Octagon stars almost immediately disappeared to … wait for it … climb a mountain.

Specifically, the Stirling Range.

Which just to get there, requires driving five hours from Perth.

“But even after winning in Montreal,” Josh recalls of his brother upsetting Belal Muhammad at UFC 315, “we had to force Jack out that night to celebrate.”

And once home in Perth?

“Yeah, he took us off to climb that peak.”

Della, see, isn’t about UFC afterparties.

Or Instagram.

Hell, even his YouTube channel has sat dormant now for five months and counting.

“Because Jack’s only goal is to become the world’s greatest fighter,” coach Ben Vickers says, “and while keeping the lowest profile”.

JDM reflects on Title triumph over Belal | 05:35

Which is why in those first few weeks owning the UFC welterweight strap, the champ’s young son Franco, aged three, dragged it about the house like Linus does his safety blanket.

Same as Maddalena’s second, ceremonial belt now hangs, almost hidden, among an array of straps, domestic titles, even medals on a wall inside his gym, Scrappy MMA.

“Which means I’ve had to install CCTV,” Vickers grins.

But as for any other changes?

“None,” Simpson says. “Of all the people I’ve ever met, Jack has the least desire for celebrity.”

Anything else?

“Well, I’m convinced he’s a psychopath,” the agent jokes. “I mean, you’ve met Jack enough times, you know him.

“Lovely guy.

“But to be that kind, that gentle outside of competition, only to then go destroy people the way he does … there has to be something there.”

Which again, is why some stories need telling, right?

And why now this week, we’re here in New York.

Where already for several nights inside a quiet New Jersey gym, surrounded only by his small team, and smaller expectation, the work goes on for this gutsy ranga lifted straight from Kingswood Country.

Truly, make a casting call for classic Aussie tough, and you won’t find better.

Take, say, that snoz bending like the will of men who face him.

Or his muscled frame forged from having spent almost every waking hour in competition with a brother who, two years older, and always several kegs heavier, still remains chief sparring partner and corner.

“And being a redhead,” Simpson grins, “he’s obviously programmed for violence”.

Which isn’t without irony, either.

Especially for a kid christened not Jack, but Giacomo.

Or as journalists here Stateside have lovingly dubbed him: Jackie Three Names.

A moniker which is itself apt for a fella now looking to make a name through violence in New York.

Or specifically, Madison Square Garden.

And against no less than Dagestani bogeyman, Islam Makhachev.

Still only six months on from winning UFC gold as a betting underdog, Jackie Three Names is now readying for arguably the Octagon’s toughest first up defence.

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Jack Della Maddalena of Australia reacts after his victory against Belal Muhammad.Source: Getty Images

With Makhachev, his rival Sunday, already wound tight by bookmakers convinced nobody beats this bearded wrasslin’ phenom from the Caucasus Mountains.

In Dagestan, young men are shaped at altitude, and in ancient villages where you lift rocks, herd sheep and, in the case of UFC great Khabib Nurmagomedov, are wrasslin’ bears by age nine.

The same Khabib, too, who will also be cornering against Della, Sunday.

Which is why inside his New York gym, the underdog quietly works.

Understanding it’s only through large chunks of hard silence that a fella who once dreamt of representing the Wallabies, and as an Aquinas College rugby prodigy, instead rises up to become UFC champ.

Initially, Maddalena had only ever wanted to make enough from this fightin’ nonsense to stay maybe a few years in the lifestyle with wife Michelle, and their two young children.

“But I guess,” he will say eventually, “I’m in too deep now.”

Isn’t he what?

Yet still, Della has little interest in everything coming should he shock the world again.

“Because I don’t want celebrity,” the fighter continues. “And I don’t want to be a household name.

“Others might.

“But it’s not who I am.

“I understand fighting, it brings notoriety. But that isn’t why I do it …”

No, Della fights because apart from being born doing exactly that, he also considers it the purest competition of any kind.

Better, it continually asks him to take risks.

And Della has long enjoyed mixing his competitive streak, and several bucketloads of natural talent, with a willingness to roll the dice.

Take, for example, he and his brother’s first ever trip to the snow, and first day on skis, when young Giacomo attempted, and landed, a backflip.

“While I’m stood there,” Josh says, “still learning to snow plough”.

“I’ll Surprise Him”: JDM to upset Islam? | 05:45

Same as Simpson will tell you how only weeks before beating Muhammad, and as a heavy underdog, UFC execs reached out with a lucrative contract renewal.

But Della, he said no. Told them he’d re-sign as champion.

“So went and bet on himself,” Simpson says.

“Had Jack renegotiated his contract before that fight, he would’ve done well. But not as well as he’s done upgrading since.

“Just like we believe in Jack, he believes in himself.”

Which again, is due almost exclusively to the work.

“Because my whole life,” Maddalena explains in a long interview of short answers, “I’ve never taken a risk without calculating it.

“It may look different from the outside, but I’ve always understood everything.”

Which means plenty inside steel cages.

“Fighting is all about decisions,” he says later. “It’s why they can’t be made on emotion. And why an emotional fighter never gets as far as the cerebral one.”

Pushed on what bore this wonderful mix of education and Evel Knievel, the champ shrugs about it being all he’s ever known.

“I’ve always enjoyed risky behaviour,” he says. “Anything to get the heartrate up.

“Maybe I was born for this, I dunno.

“But big moments don’t worry me.”

A truth proved by the fact that, despite dropping his first two professional fights, JDM has since gone nine years and 18 fights without loss.

Twice in the past two years, the Aussie has gone to split decision. And won. Same as he not only upset Brazilian Gilbert Burns with an arm broken in the first round, but has also silently carried injury into other fights.

“Because once Jack signs a contract,” Vickers says, “he doesn’t believe in pulling out.”

Which is why he hasn’t.

“Except for once,” coach continues, “way back in the amateurs”.

And why?

“Knee surgery”.

Indeed, just as Makhachev carries the bloodlines of Dagestani warriors, so Maddalena is built on the toughness of an Italian grandfather, Carlo, who arrived Down Under after WWII with little money and less English.

But what young Carlo did have?

An incredible knack for understanding machinery.

That, and ambition.

UFC 322: Della Maddalena vs Makhachev | SUN 16 NOV 2PM AEDT | Australia’s own Jack Della Maddalena puts his welterweight title on the line against Pound for Pound great and former lightweight champ Islam Makhachev in a blockbuster night of fights, live from New York City. | Order Now with Main Event on Kayo Sports.

Jack Della Maddalena of Australia fights Gilbert Burns.Source: Getty Images

Which is why after only a few months fixing typewriters and such, our teenage immigrant then asked his boss about opening a store himself.

“But Carlo,” came the shocked reply, “you can’t even speak f***ing English”.

So instead, and undeterred, our man went and found a map showing every office supply store in Australia.

And noticing Darwin didn’t have one … well, that’s where he went.

With that same business he initially opened up north having now morphed into CDM Australia — a global communication technology company of some 200 staff.

“My grandfather’s life, it was all hard work,” Maddalena says, before also stressing the same of his own father Tony, the owner of a successful debt finance company.

“Dad’s always taken things seriously and expected the same from us boys. If Josh or I had a bad showing at rugby, if we missed tackles, weren’t physical enough in a game, he’d let us know.”

Josh agrees, explaining how the brothers’ upbringing was all about winning – “we competed over everything we did” – and when morphed with talent and fearlessness now provides the “perfect storm” responsible for one of the UFC’s most exciting fighters.

And for proof, consider that in his past seven fights Della has won six UFC bonuses.

Or almost $460,000.

A bounty built not only on his famed boxing-heavy style, or incredible cardio, but sneaky strong grappling and what Carlos Ulberg, himself on the cusp of a UFC title shot, calls “hands of stone”.

Others go further still.

Take UFC cult favourite Tai Tuivasa, who hails his mate a “sick c*** who doesn’t say much … but a scary dude”.

Which is no small claim — scaring a fella who skolls beer from the shoes of strangers, and only after both have hocked a loogie in it.

‘For Volk’: JDM eyes finish in MSG | 01:53

Of course, style wise, Maddalena is similarly unconventional.

And as for him being underrated this Sunday? That’s also nothing new.

Just ask that high school classmate who, on sport day, Giacomo offered his sneakers to after the bloke had forgotten his.

A schoolboy who, then next morning, not only failed to return said kicks, but suggested something about how he likely never would.

So our chunky redhead, he beat the f*** out of him.

Same as while he doesn’t say much, Maddalena also owns one of the coldest UFC lines this year.

With his press conference sledge about fellow UFC fighter Ian Machado Garry – “I don’t think that’s Ian’s son” – as cutting, and complex, as it was brief.

“But there’s people who think my brother is just some autistic guy who likes scrapping,” Josh shrugs. “He’s not. He’s f***ing smart.”

Which is apparent in the way he wins.

And why even Australia’s top UFC exec Peter Kloczko is readying, with a victory Sunday, to immediately move his team towards making Della the megastar he has no interest in being.

“Because Jack isn’t only quintessentially Australian,” Kloczko says, “but capable of becoming the biggest star of Australian sports”.

What about the fact he doesn’t talk?

“Doesn’t matter,” Vickers says. “When you fight like Jack, you don’t need to shout on Instagram”.

Longtime Perth journalist Brett Bonetti agrees, reminding you how this is the rise of a fighter whose professional career was underway while the UFC, and cage fights generally, were still banned in WA.

“So when nobody wanted a bar of the sport,” Bonetti says proudly, “Jack was at the WA Italian Club, fighting out of a boxing ring”.

Which is a long way from not only Madison Square Garden, but that impending future overseen by Simpson, who also famously orchestrated Conor McGregor’s $45 million boxing crossover.

Jack Della Maddalena of Australia reacts after his submission victory over Randy Brown in 2023.Source: Getty Images

But as for Jackie Three Names getting a gig on Roadhouse II?

“I don’t see him taking movie roles, no,” Simpson grins. “And are we even going to see him at the ESPYS with Jon Jones? I don’t know.

“I don’t know if his personality allows that. Or even if he wants it.”

Still, some stories need telling, right?

Just ask UFC flyweight prospect Cody Haddon.

A fellow Perth boy who will never forget bumping into Jack only weeks after the welterweight’s breakout win on Dana White’s Contender Series.

“Because I’m trying to congratulate Jack,” Haddon recalls, “while he starts steering the conversation towards me.

“I can still remember him saying how the UFC is all just the same s****. Same cage. Saying how it wasn’t this big crazy thing everyone makes it out to be.

“I’m trying to congratulate him on signing with the UFC, and he’s saying how possible it is for me to make it.”

And guess what?

Make it, Haddon has.

With the hyped UFC flyweight, this Sunday, walking into MSG on Maddalena’s undercard.

Which only adds to the wonderful uniqueness of a man who, when not beating up the world’s toughest men, is at home with his family, at the beach with his family, or camping in a tent with his family.

So how the bloody hell does that guy beat a Dagestani bogeyman? A UFC lightweight king who, having vacated that throne, is now moving up to overthrow another.

Understanding that in Makhachev, you have a bearded warrior not only raised in toil, or at altitude, but who is now cornered by the mythical monster that is Nurmagomedov.

“But that whole Dagestani thing,” Della shrugs, “the idea of them being unbeatable, I think it plays on the minds of rivals.

‘You ain’t s**t’: UFC legend blasts fans | 00:37

“Breaks them even before the fight begins.”

Reminded there are also plenty tipping him to break, and the Aussie simply grins.

“I know,” he says. “They think Islam does it easy”.

So when you win?

“Well, that’s when they’ll all say ‘Oh, Islam was only a lightweight anyway’,” he says, smiling now. “They’ll say he was a lightweight who should never have moved up in the first place.

“And because I already know that’s what the narrative will be, I won’t be worried or upset when it is.

“I actually think it’s the best thing that can happen.”

Really?

“Yeah,” Maddalena grins. “That way I can just disappear again.”



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Why don’t all immigrants support progressive parties?

Why don’t all immigrants support progressive parties?

6 April 2026

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