I don’t have to tell you what was the “golden age” of heavyweight boxing. I don’t have to tell you because (a) Kieran Mulvaney already told you yesterday, and (b) if you’re any kind of a boxing fan at all, you just know. When else could heavyweight boxing have peaked but the 1970s, when Muhammad Ali, George Foreman, Joe Frazier, Ken Norton, Larry Holmes and a bunch of additional badasses who could have been champs in almost any other era roamed the earth.
But what’s the next-best heavyweight era? Well, the Big Mulvowski told you that too, but that was just, like, his opinion, man. The fact is that there’s a lot of room for debate once we get past the universally agreed upon truth that the ’70s was when they were kings.
Among the handful of eras in the mix for the runner-up spot are the 1990s, headlined by Evander Holyfield, Lennox Lewis, and Mike Tyson; and the current crew (who don’t fit quite as neatly into a particular decade), ruled by Oleksandr Usyk, Tyson Fury and Anthony Joshua.
And as 2024 gives way to 2025, we’re in an interesting place with these modern heavyweights – a place somewhat similar to where we were exactly 25 years ago, when 1999 became 2000 and all of our computers continued functioning despite great fears to the contrary.
A quarter-century ago, the three top heavyweights of the era, Holyfield, Lewis and Tyson, were mixing and matching with each other as they rolled into their late 30s, all in the later stages of their careers, having outlasted fellow early-’90s stars Riddick Bowe and second-career Foreman, and preparing to hand the reins to the Klitschko brothers.
At this moment, the three top heavyweights of the present era – Usyk, Fury, and Joshua – are mixing and matching with each other as they roll into their late 30s (yes, even AJ recently turned 35), all in the later stages of their careers, having outlasted the likes of Deontay Wilder and late-career Wladimir Klitschko, and preparing to hand the reins to … well, we don’t know who yet, but possibly Daniel Dubois, Martin Bakole or Moses Itauma.
Basically, both the start of 2025 and the start of 2000 represent the first hints of the last gasps of a silver age of heavyweights.
And that similarity is reason enough to compare, contrast, match ’em up, and try to render a judgment on whether heavyweight boxing was better 25 years ago than it is today.
Let’s start with the rankings. Here’s the current top 10, according to the :
Champion: Oleksandr Usyk
1. Daniel Dubois
2. Joseph Parker
3. Tyson Fury
4. Zhilei Zhang
5. Agit Kabayel
6. Martin Bakole
7. Anthony Joshua
8. Filip Hrgovic
9. Derek Chisora
10. Efe Ajagba
And here were the top 10 according to The Ring magazine in the issue cover-dated April 2000, representing the period ended Dec. 28, 1999 – but with one adjustment made. The Ring wasn’t singling out a “champion,” but there was indeed a lineal champ at the time, so I’ve slid everyone up one spot and then borrowed from sister magazine KO, which ranked 12 fighters per division, to fill the hole at No. 10:
Champion: Lennox Lewis
1. Evander Holyfield
2. Michael Grant
3. Ike Ibeabuchi
4. David Tua
5. Mike Tyson
6. Vitali Klitschko
7. Andrew Golota
8. Derrick Jefferson
9. Oleg Maskaev
10. Chris Byrd
It’s not easy to map the two lists onto each other and draw 1:1 comparisons up and down the line, though there are a few comps worth cherry-picking.
“Usyk = Holyfield” is the most obvious. They’re the two greatest cruiserweights of all time in whichever order you prefer, both of whom became great heavyweight champions. The ages even line up perfectly – Usyk is 37, Holyfield was 37 when we rang in Y2K. But they don’t quite align in terms of the stages of their careers. Usyk is, by all appearances, peaking right now. Holyfield, who’d had far more pro fights and, importantly, far more grueling pro fights, was in decline after going 0-1-1 over 24 rounds against Lewis in ’99.
Another equation to consider: “Lewis = Fury + Joshua ÷ 2.” In other words, Lewis, at age 34, possessed certain stylistic elements of each of his fellow British behemoths. Although maybe it should just be “Lewis = Fury + Joshua,” because Lennox was undoubtedly superior to either Fury or Joshua.
From there, the direct parallels get even flimsier.
You could call Wilder – who’s not even in the top 10 anymore – his era’s Tyson based on punching power, but you’d need to affix a whole lot of asterisks and caveats to represent the vast gulf between Tyson’s accomplishments and Wilder’s.
You could do a Parker = Tua thing based strictly on the New Zealand connection. You could even try for a Tua = Wilder comp built around power and one-dimensionality.
A Dubois-Grant comparison might have made sense with ’99 Grant vs. 2020 Dubois or 2002 Grant vs. 2022 Dubois, but at present, Dubois seems likely to make the comp look laughable.
Maybe Hrgovic is a very poor man’s Vitali Klitschko. Perhaps you could squint real hard and say Bakole reminds you of Ibeabuchi. Or if you want to go just outside the top 10 of both lists, you could write a thousand words on who wins between Andy Ruiz and John Ruiz. (Please just understand that nobody would read it.)
A perhaps more productive thought experiment is to take the 11 matchups, from champ to No. 10, and try to pick winners. Here are the pairings:
-Usyk-Lewis
-Dubois-Holyfield
-Parker-Grant
-Fury-Ibeabuchi
-Zhang-Tua
-Kabayel-Tyson
-Bakole-Vitali
-Joshua-Golota
-Hrgovic-Jefferson
-Chisora-Maskaev
-Ajagba-Byrd
It’s an excellent sign for the viability of this article that, of the 11 fights, I only find two of them easy to pick.
I make Joshua – even coming off a loss to Dubois, with his chin as questionable as ever – a solid favorite over Golota, who always found a way to lose against his best opponents. (Among the better-case scenarios for Golota is that an AJ fight would look like his November ’99 loss to Grant, in which the Pole started well but eventually caved.)
And I’d say Byrd is about a -800 favorite over Ajagba – who is precisely the sort of strong, predictable heavyweight a prime Byrd used to box circles around.
So that’s one win for the 2025 gang and one win in the 2000 column. The rest are tossups.
Consider the headliner, Usyk-Lewis. All I can say with confidence is that it would be damned close. After all, in 1999, Lewis narrowly got the better of his two fights with Holyfield – inside the building for both, I scored the first for Lewis and the second a draw, while the judges flip-flopped those results – and Holyfield was basically Usyk with a few more miles on his tires.
And in 2024, Usyk won two close decisions over Fury, which leaves it open to debate how he would do against a mountainous heavyweight who was about 5-10 per cent better across the board than Fury.
Dubois, age 27, vs. Holyfield, age 37, is fascinating. If it was the Holyfield of two years earlier who was beating up Tyson, I’d favor him without pause. If it was the Holyfield of two years later who was struggling with Ruiz, I’d comfortably favor Dubois. But this matchup is close to a coin flip.
Parker-Grant may seem easy based on what we know about Grant now, but he was at the time undefeated and had not yet had his chin and confidence shattered by Lewis.
Fury-Ibeabuchi may also seem easy if we picture the ideal version of Ibeabuchi, but there’s just so much we never learned about him, and a fighter’s greatness is always enhanced if we never witnessed his fall.
The height difference between the mountainous Zhang and 5ft 10ins Tua would be ridiculous, and Tua was always 50/50 to either chop those guys down or trudge after them round after round, barely throwing punches.
The Tyson of ’99/’00 still had every ounce of his punching power (and not much else) and used it to eradicate every C-list heavyweight placed in front of him in-between the Bite Fight and his loss to Lennox. The question is whether Kabayel, fresh off KOs of Frank Sanchez and Arslanbek Makhmudov, warrants a better letter grade than the likes of Frans Botha, Julius Francis, Lou Savarese, or Golota.
The elder Klitschko was something of an unknown quantity still at the turn of the century, just as Bakole is now. We can pick Vitali based on what he became, but we’d do so having no idea what Bakole may become.
Hrgovic, Jefferson, Chisora and Maskaev are a mass of mediocrity. Hrgovic has a lot left to prove, Chisora has proven far too much, Jefferson was all upside at the time but would soon locate his downside, and Maskaev was the sort of heavyweight who could tally either a “KO” or a “KO’d by” against almost anyone – though late ’99 and early 2000 certainly found him at the heart of his brief prime.
If forced to pick winners in every matchup, I’m landing on a score of 7-4 for the old-timers – but we’re all susceptible to favoring the eras when we came of age, and it’s entirely possible I’m showing some bias for the first group of heavyweights I covered professionally.
Still, I guess I’ll say that, by a slim margin, the heavyweight division was stronger 25 years ago than it is today.
This is a tough draw for the modern crew, though. Against the heavyweight divisions of 10, 15 or 20 years ago, it’s Team Present Day in a walk.
Eric Raskin is a veteran boxing journalist with more than 25 years of experience covering the sport for such outlets as BoxingScene, ESPN, Grantland, Playboy, and The Ring (where he served as managing editor for seven years). He also co-hosted The HBO Boxing Podcast, Showtime Boxing with Raskin & Mulvaney, The Interim Champion Boxing Podcast with Raskin & Mulvaney, and Ring Theory. He has won three first-place writing awards from the BWAA, for his work with The Ring, Grantland, and HBO. Outside boxing, he is the senior editor of and the author of 2014’s . He can be reached on , , or , or via email at RaskinBoxing@yahoo.com.