The complex mind of Derek Chisora

The story and journey of the perennial heavyweight contender Dereck Chisora is as complex as the man himself.

Sometimes jovial, sometimes not, Chisora was a man many loved to hate but who, through his honest courage and belligerent violence in the ring, can fill an arena with thousands of fans, united as they sing “Woooooah, Der-ek Chi-sooooo-ra” on loop.

But, on the eve of his 49th fight, he is readying himself for a time of silence – the lonely spell after boxing that troubles so many who are addicted to spilling blood, scoring thunderous knockouts, and receiving the adulation of an expectant and, later, satisfied crowd.

Little more than a week before what is billed as the penultimate ring-walk of his topsy-turvy career, the Zimbabwe-born Chisora meets a gaggle of UK reporters at a Russian-owned spa – or bath-house – not far from Buckingham Palace in central London.

The mood is informal. Chisora implores his hosts to bring out vodka and caviar for his guests, and as he urges a roomful of them to eat, drink and be merry, he sits down with BoxingScene to talk about his career almost being over and what feels like a victory lap before he reaches the chequered flag.

“It’s the final countdown…” he sings quietly, before discussing how it feels as the closing months and weeks on his 18-year career expire. “Yeah, very emotional. It’s emotional, emotional, emotional. It’s exciting and sad.”

Then, he hesitates for thought and carries on: “I mean like… It’s not exciting when you retire, man. You know? This is one of those things, like… you know, it’s coming to an end, something I love. You know, if you look at a journey, like… you’re boxing as an amateur, but you’re boxing for a trophy and fish and chips afterwards. Do you understand? That’s gorgeous… Then after that, you turn over as a pro and then there’s so much politics in this whole game, which is annoying.”

Such politics have caused many a fighter and fight fan to view the sport through a more cynical rather than romantic lens.

But Derek has learned to even love facets of the business that others begin to despise. He insists he’s never fallen out of love with an industry that is every bit as hostile and treacherous outside the ropes as it is within them.

“You see,” he smiles and pauses. “I love the politics of it. I love the arguments with it. I love the promoters threatening to sue you. They’re going to sue you. I love the craziness of it. I love it… That’s boxing for you.”

The snakes and ladders. 

“Yeah, that is it. ‘Oh, I’m going to sue you. I’m going to get you for this. I’m going to do this. I’m going to do this.’ But really and truly, it’s all bollocks.” 

Not everyone has the bulletproof exterior to treat it like a game. It gets very real when legal letters start to fly.

And one wonders if Chisora always had a role in mind that he wanted to play. As a young prospect, he notched several important wins but then became a renowned bad boy of British boxing. He kissed Carl Baker at one weigh in. He slapped Vitali Klitschko at another. He brawled uncontrollably with David Haye at a press conference in Germany. There were other infractions, but now it doesn’t matter. He’s adored, and he is so appreciated because, for all of those indiscretions, Chisora is a warrior. He will put his back to the ropes, invite an opponent into his private phone booth, and trade until someone is flat on their back. And the British public loves it.

His damaging war with Joe Joyce in July 2024 was nominated as one of the BWAA’s Fights of the Year.

It was as brutal as watching two men clobbering one another with bats, particularly if you stopped enjoying the guilty pleasure long enough to realize that Joyce is 39 and Chisora 41.

It was the sort of contest that divided fight fans, with some able to watch only through their fingers while others leapt for joy and high-fived one another, united by the thrilling carnage.

That some feel Chisora has more than paid his dues and that he has nothing left to prove or give is of no consequence to the Londoner.

Chisora was once seen as a villain, but that is a role he has never accepted.

“I’ve never been a villain before,” he said. “Only you guys have put this in your stuff. ‘Say he’s a villain or he’s banned from boxing.’ I’ve never been that. I’ve always been an African kid who’s come to a European country who’s trying to make a good living for himself. But at the same time, I had mistakes going on in my life. And then you guys took my mistakes and made me as a villain. Like I’m a very bad person, but really and truly I’m not. I’m a lovable guy.”

So it was merely villainous behaviour, even if he wasn’t actually a villain? 

“Yeah, it was villainous behavior,” he mischievously admits. “But you have to understand, bro. I was a villain from day one. But I was a good villain. I was like Robin Hood. Steal from the rich and put in my pocket.”

With that, Chisora smiles again – and he is keen to make sure everyone is having a good time at the expense of the promoter Frank Warren, whose Queensberry Promotions stage his fight on Saturday at the Co-op Live Arena in Manchester against the Swedish southpaw Otto Wallin.

Chisora makes sure that those who are eating are enjoying their soup and dumplings. He even breaks from the interview, as a regular in this establishment, to order more.

“Nicole? Where’s my caviar? Where’s the caviar? I promised this guy we’re going to have caviar… But the dumplings are nice.”

He looks out to several reporters, all tucking in.

“Yeah, fellas. From Frank Warren. Frank Warren. Frank Warren, we thank you very much. Get it on my Instagram… Frank Warren, we thank you very much for caviar. You know, shout out to Queensberry. You know, Eddie Hearn don’t buy me caviar. So, Frank Warren, you’re the man. Caviar for the press. Look at the press here eating caviar. You know, Eddie just eating fish and chips. Giving you, ‘Oh, we do this, we do this’. But, bollocks. Frank, you’re the man. Viva Franco! Viva Frank! Have caviar, fellas. Enjoy.”

The eccentric Chisora has been known to enjoy the finer things in life. He’s been pictured with lavish cars and likes to eat and socialize at nice places.

But the 41 year old instead beams when he speaks of his daughters rather than possessions. Of course, as for his taste in food, he’s never far from a post-fight Five Guys, too.

There have been newspaper spreads of him with fast cars, although he now sees things differently.

“What’s a nice car?” he asks.

“Posh, sports, prestige cars; I’ve seen you with a Rolls Royce,” I reply. 

“The Rolls Royce – that’s a rental, bro, that’s a rental,” he smiles again. “To be honest with you, I can get anything I want, but I don’t want it. You know, in life, if you work for it, you get it.”

It was 18 years ago when Chisora made his debut before one of the most wild fights in a British ring when Graham Earl was heroically rescued by his corner against Michael Katsidis. Later, in his second professional contest, he boxed the journeyman Tony Booth in front of around 45,000 fans at Cardiff’s national stadium, warming up the crowd in the bout that floated before Joe Calzaghe’s rapid fists blitzed Peter Manfredo.

While Chisora has fought many of the leading modern-day heavyweights, he has not fought them all. Asked whether there was one who got away, he simply replies: “All will be revealed soon.”

In 2010, he was days away from fighting Wladimir Klitschko, and it’s known Chisora was put out by that one never happening.

“It was very close,” Chisora recalls. “Emanuel Steward [Klitschko’s trainer] said my foot movement was very great at that time. So he pulled him out.”

Klitschko, it was announced, had a torn abdomen. 

Asked if a lucrative all-London fight with Anthony Joshua was ever on his agenda, Chisora coyly replies: “I don’t know. Who knows? A couple of them have got away.”

Chisora is signed to Joshua’s management company, and their children go to the same school.

But, win or lose against Wallin, fight 50 will happen if Chisora has his way, so he is not saying never to anyone.

“No one has got away yet because there’s one more fight. So don’t… Might be after a flip of a coin…” 

With Chisora holding court and reporters waiting to hang on his every word, he says how his time at this bath-house is his version of golf – a game he apparently can’t stand. Instead, he discusses hot saunas and cold-water plunges. If he feels battered from training, he will book half a day in here and feel brand new. He dares the media pack to try the facilities, and many laugh it off, but it piques the interest of others. Is Chisora joking? Is he being serious? It’s often hard to tell.

But with Chisora’s attention being sought elsewhere, BoxingScene focuses on the task at hand and asks the heavyweight more pressing questions.

He has boxed 48 times as a pro. He’s competed in 334 rounds. He has been on the wrong end of a couple of ugly knockouts in a career in which he has been victorious 35 times – with 23 stoppages – and recorded 13 losses, four by knockout. He’s fought and raves about the ability and greatness of Oleksandr Usyk. He’s also fought Tyson Fury three times, Dillian Whyte, Joseph Parker and Kubrat Pulev twice, and, among many others, David Haye, David Price, and Agit Kabayel.

He’s gulped down gigantic bombs for years – including as far back as against Vitali Klitschko in 2012. Sure, his fists have wreaked their own havoc. Ask Carlos Takam, traumatised by one of the great overhand rights London has witnessed.

They sang “woooooahhh Der-ek Chi-sooooo-ra” long and loud that night. 

That, of course, is one of the many things “Del Boy” will miss.

Life after boxing is not something he wants to embrace.

“To be honest,” he adds, lost in thought and looking into the middle distance. “I’m dreading [life after boxing], because I don’t know what’s down there. I don’t know. I’ll miss all of this. The whole thing. Everything. I think I’ll miss the routine. I’ll miss the discipline; the runs; the sparring. And the biggest drug for me, yeah, is the fighting. It’s the fighting.”

The was with Joyce was a typical Chisora Pier 6 brawl. There were moments when a groggy Chisora, fighting through a haze of trauma, looked to be almost delirious – boxing through the realms of exhaustion where only the truest of boxing hearts can beat.

But even then, with fatigue attempting to suffocate him, Chisora knew what the plan was. It was to dig a deep hole early on and not allow Joyce to climb out.

Chisora knew it was going to hurt, but it’s a price he has always been willing to pay.

“Nothing matters because, you know, with Joyce, I knew he’s going to think in the later rounds I was going to run out of energy and then he’ll come stronger, but I just carried on,” he said. “We trained by winning the first seven rounds and then from then… It’s like a sprint. You know, when a guy was doing a 400 [metres], he just takes off the blocks and just carries on running? And everyone would just go with him. So what I did with my trainers was to say, ‘We’re going to have to win the first six rounds or seven rounds’. And from then I could not stop. I just carried on.”

And that is what he does. In the ring, out of the ring, he still carries on. But not for much longer.

There are concerns felt throughout much of the fight community for Chisora’s long-term health. His odometer has gone around the clock a few times and been reset.  

The man who many struggled to appreciate at the start, who many disliked in the middle, now worry for him.

“Don’t be concerned for me moving forward, fellas,” he says. “I can still write my name. But sometimes I forget where I live!”

He cracks into a loud laugh.

“I drive past my house about six times and my wife goes, ‘Where are you going?’ I’m like, ‘Oh, that’s where you live’ and I’m like, ‘I’m joking’.” 

Is it something he seriously considers – CTE and how life might look 20 years from now?

“Mate, can I be honest with you?” he confides. “I was born damaged, bro. I’m damaged already, bro. If I was not damaged, you think I’d be doing boxing?” 

BoxingScene exits the bath-house having secured the Chisora interview. Was Chisora being serious about stripping off in front of the press pack? Was it a ruse? Was he playing?

Later, Wally Downes of The Sun sends BoxingScene a picture of he and Del wrapped in only towels with steam billowing in the background. The Stomping Ground’s Charlie Parsons uploads a video of him taking a cold plunge with Chisora looking on.

That was typical Chisora. He was playing but he meant it. It was a joke but he was being serious. We might never get to the bottom of what makes Derek Chisora tick, but at least he’s okay with his life in boxing and his time under our, at times, forensic microscope.

“Am I satisfied?” he wonders aloud. “Yes. Nah, you’re never satisfied as a man. But if everything comes in tomorrow, I’m happy. Yeah, I’m happy. With myself, my kids are happy.

“Everybody’s healthy.”