Yet after all the call-outs, all the failed negotiations and the endless finger pointing – not to mention that controversial $50million (£39m) email offer – there has never been a better time for this faceless rivalry to be settled.
Both Joshua and Wilder are still reeling from consecutive defeats against one of the division’s new rulers. AJ is unified champion no more after twice failing to solve the Oleksandr Usyk puzzle, while his American counterpart lost the WBC title and then failed to reclaim it in brutal losses against Tyson Fury.
Now, after returning to winning ways over the past eight months, the crestfallen pair are finally poised to meet in an unprecedented double-header in Saudi Arabia this December.
Saudi chiefs are lining up Joshua vs Wilder to take place on the very same card and night as an undisputed showdown between Usyk and Fury. The plan is then for the winners from each bout to lock horns in a glamorous finale – presenting Joshua and Wilder with a lucrative opportunity to propel themselves back to the top.
Anthony Joshua (left) and Deontay Wilder (right) have been on a collision course for six years
Eddie Hearn claims a deal for Wilder vs Joshua in Saudi Arabia is now close to completion
The fight could take place in an unprecedented double header card also featuring Tyson Fury (left) vs Oleksandr Usyk (right) for the undisputed heavyweight title
As little as 10 months ago it seemed AJ had a long and arduous road to redemption ahead of him after another defeat at the hands of the masterful Usyk. While producing a much-improved display in the rematch, he had ultimately been outclassed once again over 12 rounds. And with his tormentor free to move on, another title bid appeared further away than ever. Some even questioned whether it was time to bow out.
Just one win later, and an unconvincing win at that over rank underdog Jermaine Franklin, the Brit now finds himself on the cusp of a money-spinning encounter with Wilder in the Middle East.
It is a match-up that defies championships, such is the stature of the fighters involved, the lengthy rivalry they have shared and the interest it would therefore generate. According to Eddie Hearn, a deal is ‘close’ and could be announced as soon as next week.
All four heavyweights involved in Saudi’s revolutionary mini-tournament are expected to sweep up colossal paydays which will dwarf the highest earnings of their careers.
So why, then, is Joshua willing to risk it all in a needless rematch with Dillian Whyte beforehand?
Eager to box three times this year, gel further with new coach Derrick James and ensure he is well prepared for the clear threat a bout with Wilder poses, AJ is keen to take on arch-nemesis Whyte for a second time in London this summer.
This week Hearn sent a fresh contract to Whyte for a proposed August 12 date at the O2 Arena, albeit with terms the Brixton man is not entirely pleased with. The general consensus is that an agreement will soon be reached, pitting Joshua and Whyte against each other once more, almost seven years since their last meeting.
Joshua looked to have a long road back to the top ahead of him, but after one win he now stands on the cusp of a money-spinning encounter which could propel him back into the mix
Beating Wilder would potentially set up a huge showdown with Fury or Usyk for all four belts
Joshua will head into the rematch as favourite despite his recent fall from grace, though this perhaps says more about Whyte’s even steeper decline, with his best win of the last four years coming against a 41-year-old, Covid-worn Alexander Povetkin.
There is a sense that is AJ taking a risk against Dillian Whyte (pictured)
Last time out Whyte’s hand was raised against Franklin, yet most were of the opinion it shouldn’t have been. Joshua’s win over the American was less disputable but it was far from convincing.
The former Olympic champion was gun-shy on his big debut under James, too cautious about what was coming back from Franklin than going for the jugular himself. At the peak of his powers, before Andy Ruiz Jnr brought him crashing down to earth, a prime AJ would never have gone the distance with a fighter of Franklin’s ilk.
Thus, a second battle with Whyte is by no means a foregone conclusion – simply because of how shaky and beatable both men have looked of late.
Franklin may have got the better of him in most people’s minds, but for Whyte little will get the juices flowing more than another crack at his old amateur foe.
The score is locked at one apiece after Joshua avenged his defeat in the non-paid ranks with a vicious knockout as professionals in December 2015. Whyte will be as desperate as ever to settle the score once and for all.
The history between them means Whyte remains one of the most dangerous opponents for Joshua outside the current champions, regardless of how poor he looked in his long-awaited title shot against Fury last year. If that version of Whyte turns up at the O2, it would be tough to make a case for him.
Whyte will be an underdog heading into their rematch because of how poor he looked last time out against Jermaine Franklin (right)
Joshua’s win over Franklin was less disputable but it was far from a convincing performance
Whyte will also be desperate to avenge his defeat against Joshua back in December 2015
However, with the dangling carrot of a Wilder blockbuster already being served up, Joshua is taking an unnecessary risk by reigniting his bitter feud with Whyte this summer.
Potentially hundreds of millions of pounds, a mouthwatering challenge he has been sizing up for six years and, more still, his boxing career will be in the balance when he undergoes this warm-up in London, giving Whyte even more incentive to inflict what would probably go down as a marginal upset.
Many will opt for familiar logic when backing this chosen path for Joshua: if he isn’t good enough to beat Whyte, then what business does he have facing Wilder anyway?
Such thinking may well prove bang on the money, regardless of what route he goes down. Though it can be argued that a more risk-averse opponent and routine victory would both restore confidence and allow Joshua to work on more specific elements of his game with James in his corner.
In Whyte, a straight-up shootout with a man looking to take his head off awaits. Game plans and blueprints often go out the window on these occasions. Yet with that being said, perhaps this is exactly the kind of preparation needed for someone as vicious and gung-ho as Wilder, who will not be promising a tit-for-tat chess match.
This grudge match seems like a risk AJ doesn’t need to take with Wilder waiting in the wings
Defeat would bring his Saudi plans crashing down and all but end his heavyweight career
Toppling Whyte again, even if on the scorecards, would mark significant progress for Joshua at a time he requires an upward trajectory more than ever. And given how comfortably Fury dispatched of the Body Snatcher at Wembley, if James can get AJ firing again a knockout would have to be fancied.
That outcome has to be the prime objective for AJ heading into one of the most dangerous challenges of his professional career to date. But should this risky warm-up backfire, defeat will likely spell the end of his boxing journey.
Whyte’s claim that negotiations are being held up by Joshua’s insistence on a one-way rematch clause is puzzling given he surely will not need one. Lose here and dates of destiny with Wilder and Fury are essentially gone forever.
AJ’s heavyweight hopes will hanging by the very last thread against Whyte in August.