Fights that happened vs. when they should've happened

Thought it'd be fun (well, bittersweet) to put together a thread of big-name fights that happened past their sell-by date, and making a case for when those fights should've happened to have had more value legacy-wise, been better spectacles etc. I'm looking at the kind of fights that could've been legacy-defining classics at the right moment in time, but ended up being kind of meaningless or at least 'meh.'

I'll start:

Lewis vs. Tyson: fought in 2002, should've fought in 1996 (6 years earlier)
Lewis' victory over the shell of Tyson is probably one of the most meaningless 'name' victories in boxing history. Tyson's prime was really in the late 80s, and with Tyson's prison time there was never really an 'optimal' time for them to fight prime vs. prime.

That said, Tyson looked solid on his comeback run, picking up a title off Frank Bruno and coming off a bunch of KO victories in quick succession. It was his last solid 'run' in the division. Lewis himself was in his prime around this time, with victories over Mercer, Morrison, Bruno, and Tucker behind him. Certainly, Lewis would still have the advantage in terms of prime-ness, and you'd have to favour him, but at that point in Tyson's career it'd have been a much more meaningful fight legacy-wise rather than the sad affair vs. a totally finished Tyson whose subsequent fights showed he had nothing left.

Khan vs. Brook: fought in 2022, should've fought in 2011 (9 years earlier)
This is a tough one, because Khan's prime was around 2009-2011, when Brook was still fighting jobbers (which is strange, seeing as Brook's career started before Khan's). At this time, both men had 20-something fights, and Khan was still world champ before his career went on the slide following successive defeats to Garcia and Peterson. Khan still had his aura, while Brook had picked up decent wins off the likes of Galarza and Lovemore Ndou.

At the very latest, Khan could've got a shot at Brook's world title after Brook won it off Porter in 2014, with Khan coming off a nice series of wins over the likes of Collazo and Devon Alexander. Khan's chin was probably broken at that point (though arguably, it always was), but at least he was naturally fighting at welterweight around that time.

 

Tyson - Holyfield: Yep, that's a good one. Also kind of links to my own about Tyson-Lewis, because if Holyfield had fought Tyson pre-prison, there'd have been less call for them to fight post-prison, and at the time when Tyson fought Holyfield is when I would've had him fighting Lewis. It's a shame that Tyson's biggest fights happened when he was post-prime and shot vs prime and post-prime, respectively.

Ali - Holmes: I'd argue that Ali and Holmes should never have fought. Ali's prime was in 65-67, and he was already way past it and probably starting to get Parkinson's by the late 70s. I think it would've been marginally more competitive, but still a sad spectacle.

Bowe - Lewis: Yep, cheating haha, but that would've been great to see.

Fury - Usyk: Agreed, could've happened a bit sooner, but I don't think the 1.5 years would've changed the dynamic of the fight too dramatically. Fury/Usyk 1 is still a classic in my eyes, between the top 2 of the HW division, so I'm happy we got to see it (and the follow-up happened nice and soon after to wrap up all doubt, though it was less exciting). I don't feel like we were 'robbed' of anything there, so it wasn't too egregious.

 

Probably the absolute biggest loss to boxing that one. Two ATGs at the height of their powers, and it didn't happen due to weirdo boxing politics (I don't really know who to blame). Came 5 years too late. Granted, both were still very high-level boxers, but it was far from fight that we should've got in 2010, with Pacquiao having lost 2 of his previous 5 and clearly being on the slide.