IN keeping with the tradition of selling a product as something it’s not, the promised 41 potential fights for Dereck Chisora the title of this article promises will instead amount to something closer to four. (Sorry.) No doubt were he permitted to box another 41 times, and be compensated accordingly, Chisora would love to box another 41 times, yet the truth is that 41 is a number even Chisora is unlikely to reach before his tumultuous but entertaining professional career is over.

For the purpose of this piece, the number 41, rather than some arbitrary number plucked out of thin air, is in fact the number of fights Chisora would have to complete to match the current total of his former opponent Danny Williams, whom Chisora defeated in 2010. Now, admittedly, getting to 85 pro fights is probably not a target of Chisora’s at this point, and hopefully never becomes one, but nevertheless Williams, a man still fighting in 2022 at the age of 48, should still, in my opinion, be viewed as a target and measuring stick – of sorts – for someone like Chisora. He should be seen, by Chisora, as not someone to try to one day match, no, but as perhaps someone whose career trajectory they should look to avoid.

For, after all, while Williams enjoyed a purple patch in 2004, the year in which he shocked the world by beating Mike Tyson and also challenging Vitali Klitschko for the WBC heavyweight title, he has since unfortunately become a cautionary tale. He is considered now to be a somewhat tragic figure stuck in boxing – stuck, that is, doing this thing he never even enjoyed all that much in the first place. A good guy, it’s a path Williams has, alas, chosen for one reason and one reason only: to provide for his family.

Chisora, likewise, is a man who sees no reason to call it a day. He, of course, is not only in a much healthier position than Williams was at the age of 38, but has also given us no reason to believe he will still be boxing 10 years from now. The only concern with Chisora is that, unlike Williams, he is someone whose love for a pound note is matched – almost – by his love for a fight, which could, you never know, create an attachment tough to break in moments when common sense should ideally prevail.

Still, for now, Chisora, 33-12 (22), is okay. Though nowhere near his best, he is coming off a win at least – a split-decision against Kubrat Pulev on Saturday (July 9) – and, whether winning or losing, continues to operate at a decent level, displaying obvious signs of regression but not yet triggering any jarringly loud alarm bells. He has recently lasted the distance with Oleksandr Usyk and Joseph Parker (twice) and, on paper, seems to still have enough about him to carry on. It’s only his style, in fact, and both his willingness and need to take punches – or, as he calls it, “entertain” – that has the more compassionate among us worried about his future, more so than his form in the present. That will presumably never change. Moreover, given his style, age, and thirst for both money and relevance, the most likely scenario for Chisora is that he keeps going in the same direction until he can function no more – both in fighting terms and overall career terms.

If that’s to be the case, he will require opponents. Maybe a few of them. Maybe lots of them. Whatever his needs, though, here are four short-term possibilities: three British, one American, all potentially hazardous and career-ending.

1) Dillian Whyte

This is perhaps the only fight Chisora should be actively chasing, not just because the two have history, having fought twice already, but because, based on those two previous fights, Whyte is someone with whom he can be competitive. He didn’t win either of their previous fights, no, and he is probably no better now than he was then, yet at least Chisora, stylistically, knows he has been a handful for Whyte in the past and would therefore take confidence into any prospective third fight between the pair.

Furthermore, just as Chisora would be different third time around, so too would Whyte, someone who has since 2018 (the year of their last meeting) been badly knocked out by both Alexander Povetkin and Tyson Fury. He has wounds to lick and demons to exorcise right now and a third match with Chisora, when already 2-0 up in the series, could be just the ticket he needs to get back on track and jumpstart his career.

Dillian Whyte vs Alexander Povetkin
Whyte avenges his loss to Povetkin

2) Joe Joyce

This, a fight discussed for some time, would be an intriguing match for several reasons. The first reason has a lot to do with the dynamic between the pair, in terms of personalities, and how this would play out before the fight and also during the fight: Joyce, the monosyllabic destroyer with an interest only in juggernauting forward and through opponents, versus Chisora, the unpredictable wild man who needs an opponent with whom he can engage in order to feel something, anything.

Secondly, their two styles would presumably blend extremely well, given neither like to take a backwards step, nor, for that matter, protect themselves. It could, in fact, make for quite the brutal and gruelling contest, which, if you ask them, is exactly what the two of them want. Only, at this stage, what a fighter wants and what a fighter needs is a difference Chisora could discover the hard way should he cross paths with the relentless Joyce anytime soon.

Joe Joyce wades into Christian Hammer at Wembley (Photo by James Chance/Getty Images)

3) Daniel Dubois

It could be argued this would be the most winnable fight for Chisora on the list, based purely on Dubois’ lack of professional experience and inexperience with styles like Chisora’s. Then again, Dubois, also from London, is on a rich vein of form at the moment and has rebounded well since being broken up by Joe Joyce in 2020. He has since that night stopped Bogdan Dinu inside two rounds, Joe Cusumano inside one, and last time out finished the previously unbeaten Trevor Bryan inside four. That win in Miami landed Dubois the ridiculous WBA ‘regular’ heavyweight belt, yet, far better than that, it increased his relevance on the world stage and made him once again an alluring target for perennial contenders like Chisora, someone whose aggressive style could offer Dubois the chance to show he has heeded the lessons dealt out to him by Joyce two years ago.

Dubois knocks out Bryan, David Martin-Warr/DKP

4) Deontay Wilder

Last and definitely least, the prospect of Dereck Chisora fighting Deontay Wilder in his 39th year is one proposed only by Deontay Wilder, people who deep down hate Dereck Chisora, or Dereck Chisora still high on the adrenaline of a rare victory. This recommendation could – and has – come from any of those sources and we must now, for Chisora’s sake, safeguard against a farfetched sadistic fantasy becoming a reality in the not-too-distant future. To do this, we need to treat a potential Wilder vs. Chisora fight with all the disdain it deserves and offer nobody – not Chisora, Wilder, or any promoter – a sliver of encouragement to get the fight made.

For, it’s true, if there is one opponent Chisora really doesn’t need to be fighting at this point in his career it’s a man with the one-punch, truth-telling power of Deontay Wilder, he of 41 knockouts from 42 wins. Barring a miracle, that is a linkup that would end only one way and, worse, it would end for Chisora in a way both conclusive and undoubtedly painful. It would likely produce the kind of ending he has so far managed to avoid; a loss not confirmed by judges, not one he could argue, and not one from which there would appear a route back. In short: avoid at all costs.

Tyson Fury vs Deontay Wilder
Wilder trades with Fury (Frank Micelotta/Fox Sports/PictureGroup)