There was once a time when Josh Kelly and Conor Benn were on a collision course, with a fight between the pair seemingly inevitable. Back then they were unbeaten welterweights and were both so different in terms of fighting styles and personalities it appeared a natural fight to make; a big one, at least domestically. 

Then, however, Kelly suffered his first pro loss against David Avanesyan in 2021 and the dynamic changed somewhat. Whereas before most were of the opinion that Kelly, the superior technician and more decorated amateur, would have his way with Benn and the fight would be a mismatch, now the gap between them had all of a sudden closed. The appeal of it had also dwindled on account of Kelly’s first defeat. 

Rather than think of Benn, the Sunderland man now had other things on his mind. Now he had some rebuilding to do and a comeback to plan. In the meantime, Benn, still unbeaten, continued to win, invariably by knockout, and continued to grow his profile. Soon, in fact, there was a sense that Benn had overtaken Kelly, if only commercially. This thought was then solidified when Chris Eubank Jnr, a middleweight, expressed an interest in fighting Benn in 2022, after which everything changed – for a variety of reasons. 

Three years later, Benn and Eubank Jnr have now fought – a fight Eubank Jnr won via decision last month – and Kelly has lifted the British super-welterweight belt, which he no sooner relinquished. In his past fight Kelly defeated Ishmael Davis at a weight of 159 pounds – essentially middleweight – and on June 6 he will fight again at that weight, this time against Flavius Biea, an unheralded Romanian whose record is 24-1 (12). 

It is, on paper, another routine assignment for Kelly – one he should win – and it pales in comparison to the fight Benn, his one-time rival, had at Tottenham Hotspur Stadium recently. That is more a reflection of their respective profiles than anything to do with talent, of course, yet it is no less noteworthy given how their rivalry started and how sure Kelly is of his superiority. 

“I’d probably knock Conor Benn out, if not totally outbox him, and I believe I’d totally stand Eubank on his head,” Kelly, 16-1-1 (8), told Sky Sports this week. “I don’t think Eubank would go anywhere near me. I think I’ve got more of a chance getting the Conor Benn fight. If he can’t make 147 [pounds] anymore, or struggles to get down there, I’m the biggest guy at 154.” Asked then if he would meet Benn at either 154 or 157 pounds, Kelly showed no hesitation: “In a heartbeat,” he said. “It wouldn’t even be a question. It would just be like, ‘Yes, sign, done.’”

Now 31, Kelly still has time on his side, but has been a pro for over eight years and has learned during those eight years that it takes more than just talent to reach the very top. He has, along the way, suffered a setback or two – including that Avanesyan defeat and a draw against Ray Robinson in 2019 – but has always responded well to adversity and shown a steeliness which belies his flash style and propensity to showboat. 

And yet, if there is one thing Kelly hasn’t cracked so far it is landing a big fight, with many of his fights those of the low-key variety and only his British title triumph against Troy Williamson, arguably his best performance, feeling remotely big at the time. It is in this area, and only this area, Kelly feels inferior to Conor Benn.

“Conor’s a very clever fighter in terms of marketing,” he said. “I should take a leaf out of his book. I should start shouting everybody out. I should just say, ‘I’m only fighting the ones who are going to make me the most money’.”

Though he made this claim half-jokingly and with a smirk, there is an element of truth to Kelly’s words, and in his voice a hint of resignation, too. After all, the fight between Conor Benn and Chris Eubank Jnr was never highly anticipated and popular on the basis of artistic merit or the skills of the two fighters involved. Instead, the reason it attracted 60,000 fans to a North London football stadium was because it was big and brash and because it was dirty and ugly in the best way possible. In which case, maybe the problem with Josh Kelly, a fighter known as “Pretty Boy”, is that he has tried to do things quietly and cleanly for too long. He should perhaps remind himself that this is boxing. There is no sport uglier.