Derek “War” Chisora is set to lace up the gloves one last time this December in Manchester for his 50th professional bout — a milestone that caps off a career filled with wars, controversies, and unforgettable moments. Known for his iron chin, relentless pressure, and larger-than-life personality, Chisora has fought nearly everyone worth mentioning in the heavyweight division. He has plenty of losses but he always has been giving everything in the ring and must be the most popular ”gatekeeper” of the last 20 years. This man has given so much to boxing and he deserves an epic farewell.
But the question fans can’t stop debating is: Who should he face in his farewell fight?
Let’s break down and discuss 5 possible opponents.
1. A Rematch With Dillian Whyte
One of the most obvious choices is Dillian “The Body Snatcher” Whyte.
The two men produced two brutal classics, including a 2018 Fight of the Year contender that ended with Whyte knocking Chisora out cold in round 11.
- Why It Makes Sense: The rivalry is real, and fans know it guarantees fireworks. Both men are on the back nine of their careers, so neither has title pressure anymore. Derek has 2 losses against Whyte and I see a big chance Derek would beat Whyte in a 3rd and final bout as Whyte is on decline.
- The Counterpoint: Some argue it feels recycled — a fight we’ve seen twice before. If this is truly Chisora’s last hurrah, maybe it should be something bigger.
2. A Passing-the-Torch Fight Against Moses Itauma
On the opposite end, some fans want to see Chisora’s swan song used as a showcase for the next generation. Moses Itauma, the young heavyweight prodigy from Britain, is tipped as a future world champion.
- Why It Makes Sense: Itauma would gain priceless experience against a durable veteran, and Chisora could give fans a glimpse of the division’s future.
- The Counterpoint: Many feel it’s unfair to pit a 40-year-old warhorse against a 20-year-old phenom in a fight that would inevitably highlight Chisora’s decline rather than his glory. Especially after seeing Itaumas absolute destruction of Dillian Whyte, I wouldn’t like to see this fight. Chisora deserves a great farewell and going up against a very dangerous youngster with no world title is high risk – low reward. It’s also a big risk for his health after a long career with many hard fights. Itauma is very fast and powerful, but Chisora has a tendency to eat 2 shots for the opportunity to give one. Very entertaining but very dangerous, especially against someone like Itauma.
3. A second fight With Oleksandr Usyk
Chisora fought Usyk in 2020, pushing the Ukrainian harder than most people expected before losing on points. A rematch may sound odd (since Usyk is now at the very top of the sport), but there is a possibility that Usyk will give Chirsora a chance.
- Why It Makes Sense: Usyk is the current undisputed heavyweight champion, and facing him again would allow Chisora to end his career against the very best. Chisora has had a couple of great wins at the end of his career. Usyk seems to have a lot of respect for Chisora but I don’t believe Usyk sees Derek as a serious treat. Usyk has grown in to the heavyweight devision and made a lot of progress since 2020. Chisora on the other hand has nothing to lose, he can finish with one last wat about the undisputed heavyweight title. This would be a great last fight for Derek win or loss.
- The Counterpoint: Usyk is in his prime and chasing legacy-defining fights. In one way this fight docent really make sense. Its hard to argue for Derek being in the discussion for an undisputed heavyweight fight. But to be fair Chisora gave Usyk a hard fight in 2020 and if it’s positioned as more of a celebratory send-off it makes more sense. And we know for sure that Derek would give his absolute everything and that it would be an entertaining fight.
4. A Domestic Blockbuster With Anthony Joshua
Anthony Joshua is still one of the biggest names in world boxing, and a fight with Chisora would sell out instantly. While Joshua is chasing a world title return, a domestic showdown with “Del Boy” would be a massive event. To popular British fighters, lots of money in the pot.
- Why It Makes Sense: Two British heavyweights, both former title challengers, colliding in front of a packed Manchester crowd would be a fitting farewell. Great fight for both of them. If Joshua wants to get back and position himself as a serious contender, a fight against Chisora would be a great first step. For Chisora its also a great fight. It wouldn’t be any shame losing to Joshua but I still see a serious possibility that Chisora could come out victorious. Joshua has shown signs on a weak chin and he doesn’t like it when it gets really rough in there. Chisora can both pack a punch and he is very hard to be in the ring with. He will come at you and it will hurt A LOT even if you win against him.
5. A Fan-Friendly Brawl With Deontay Wilder
If the goal is pure chaos, then facing Wilder — a man with maybe the most dangerous right hand in boxing history — could deliver the ultimate high-risk, high-reward fight.
- Why It Makes Sense: Wilder’s power vs. Chisora’s aggressive pressure is the kind of clash fans love. I think this would be a great fight for Derek. Wilder can punch very hard but he doesn’t like being pressured since ha can’t fight in the inside. If Wilder doesn’t manage to land big when Chisora comes in, this could be a nightmare for wilder.
- The Counterpoint: Wilder is still chasing world-level fights, and may not want to risk it against Chisora. It’s stylistically a bad fight for Wilder. Wilder has pretty poor movement and no inside game what so ever. If Derek can manage to get on the inside and stay there with Wilder pressed against the ropes, Wilder can’t win. I see a big risk that it’s just what’s going to happen, and I think wilder and his team knows that as well.
The Verdict: What Does Chisora Deserve?
The debate boils down to what kind of farewell fans (and Chisora himself) want:
- A rivalry revival (Whyte)
- A passing of the torch (Itauma)
- A world-class sendoff (Usyk)
- A domestic blockbuster (Joshua)
- Or an all-out war (Wilder)
Whatever the choice, one thing is certain: Derek Chisora has given everything to boxing. His final fight should honor his warrior spirit — and give fans one last unforgettable night.