Some of you younger readers may not be aware of this, but famous podcaster Conan O’Brien used to host a late-night television show. And on that show, he had a recurring bit called “In the Year 2000,” in which he and sidekick Andy Richter made satirical predictions about what the future might have in store.
For the record, at no point did O’Brien correctly predict that, in the year 2000, Mike Tyson would threaten to eat Lennox Lewis’ unborn children. Sometimes, truth is stranger than what comedy writers can conceive.
Anyway, back in the ’90s on Late Night, the joke was that 2000 wasn’t really that far away but they were acting like it was unfathomably distant. Now, in 2025, the year 2000 actually is quite distant (in the other direction).
Twenty-five years is a long time in boxing. Long enough for every division to turn over several times (yet somehow not quite long enough to get rid of Manny Pacquiao).
A quarter-century is the kind of distance that lends itself nicely to comparisons. How much changed in boxing from 2000 to 2025? Is the sport healthier now or was it healthier then? Those are compelling topics … that I will not explore in this column.
Instead, I will simply explore: How do the best fighters of today compare to the best fighters of 2000?
The nearest ratings period for The Ring (the magazine that employed me at the time) to exactly 25 years ago ended on November 7, 2000, as recorded in the issue cover-dated March 2001. So I’m using the No. 1 fighter in each division (at a time slightly pre-dating the reintroduction of The Ring championships).
For today’s fighters, I’m using the Transnational Boxing Rankings Board’s ratings rather than The Ring’s, because … well, I have my reasons. In divisions where TBRB has a lineal champion, he gets the call, and in divisions without a champ, it’s TBRB’s No. 1-ranked fighter.
A caveat before we begin: More is known about the fighters from 2000. We saw how their careers played out, we know who made the Hall of Fame and who didn’t. And there is a tendency to remember athletes of the past at their very best.
Then again, many of today’s champions are undefeated. We have never witnessed what it takes to beat them. For nearly all of the 25-years-ago boxers, “Ls” were eventually taken and therefore we can picture exactly what that looks like.
Hopefully these potential biases will cancel each other out as I pick 17 winners pairing the best of the modern moment against the best of Conan O’Brien’s distant future.
Heavyweight: Oleksandr Usyk vs. Lennox Lewis
As great as Usyk is, as much as he keeps proving it, and as many “super heavyweights” as he outboxes, Lewis remains one of the first heavyweight champs of the past that experts point to when seeking to name someone the Ukrainian wouldn’t have beaten. Lennox wasn’t perfect, but he is the ultimate example of size, skill and power all coming together. If Anthony Joshua could twice fall just short against Usyk, then Lewis, a superior version of Joshua, should narrowly get the job done.
Pick: Lewis
Cruiserweight: Jai Opetaia vs. Juan Carlos Gomez
Germany-based Cuban Gomez was a fine cruiser titlist, but he never really faced noteworthy competition until years later at heavyweight. He took a title from Marcelo Dominguez, turned back former beltholder Imamu Mayfield. Meh. Aussie Opetaia’s two wins over Mairis Briedis probably give him a better resume already. But it’s not about resume. It’s about ability. And I’ll take Opetaia there, too, in this battle of heavy-handed southpaws. His hand speed and explosiveness would prove a bit too much for Gomez.
Pick: Opetaia
Light heavyweight: Dmitry Bivol vs. Roy Jones Jnr
Bivol is a heck of a fighter. He can use his jab and his discipline to make this a relatively challenging night’s work for a prime Roy Jones. But it’s a prime Roy Jones. Let’s not overthink it. There’s a good chance he carries Bivol in the back half of the fight rather than trying to finish him off, but he still wins with room to spare.
Pick: Jones
Super middleweight: Terence Crawford vs. Sven Ottke
In hindsight, it seems silly that The Ring editors had Ottke ranked ahead of Joe Calzaghe — but the Calzaghe of the moment was coming off wins over Omar Sheika, David Starie and Rick Thornberry, so it was actually quite justifiable. Regardless, the rankings are the rankings. And “Bud” Crawford is Bud Crawford. Not sure I’d pick him to overcome Calzaghe at 168. But even if we assume Germany’s worst judges get the assignment, I’m picking him to top Ottke.
Pick: Crawford
Middleweight: Janibek Alimkhanuly vs. Bernard Hopkins
This is where we see that my word counts are going to be wildly inconsistent from one matchup to the next. Sorry, Alimkhanuly superfans, but B-Hop does whatever he wants against him.
Pick: Hopkins
Junior middleweight: Sebastian Fundora vs. Felix Trinidad
It’s tempting to declare this another easy pick, an all-time great in “Tito” Trinidad against an opponent in Fundora who’s proven far less. But nobody is easy to pick over the unicorn Fundora — who keeps looking more fearsome with every fight. Still, figure on Trinidad’s left hook taking Fundora out eventually. I’m favoring the Puerto Rican icon, but there’s nothing easy about it.
Pick: Trinidad
Welterweight: Brian Norman Jnr vs. Shane Mosley
Maybe this is one of those matchups we’ll reassess a couple of years from now, if Norman beats Devin Haney handily next month and unifies some more belts. Perhaps Norman will prove to be a special fighter. But we know for a fact that the welterweight “Sugar Shane” of the year 2000 was about as special as they come. Norman has never seen anything like Mosley, and that will still be true after Norman has faced Haney.
Pick: Mosley
Junior welterweight: Teofimo Lopez vs. Kostya Tszyu
Which Lopez are we going to get? At his best, he beat Vasiliy Lomachenko. At his worst — even ignoring his loss to George Kambosos, for which he was physically compromised — he’s struggled mightily with cuties like Sandor Martin and Jamaine Ortiz. Tszyu was no cutie. But he was consistent and hard to discourage and he found weaknesses if the other guy had lapses. I’m thinking Tszyu eventually finds Lopez’s weaknesses.
Pick: Tszyu
Lightweight: Shakur Stevenson vs. Jose Luis Castillo
2000 was before Castillo had fought Floyd Mayweather and pushed him to his limits, but we are judging this matchup with the knowledge that he was capable of that. And you could rightfully say “Shakur is no Floyd” and make Castillo the pick. But the evidence of how Stevenson turned back William Zepeda and Oscar Valdez — neither as well-rounded as Castillo, but still, reasonable facsimiles — is tough to ignore. Truly elite skill, which Stevenson possesses, tends to win out, even if, in the case of both Mayweather-Castillo fights, it didn’t win out by much.
Pick: Stevenson
Junior lightweight: Emanuel Navarrete vs. Diego Corrales
Not only is Calzaghe left out of this exercise, but so is Mayweather! This was a couple of months before Mayweather and Corrales fought, and, crazy as it may now sound, sportsbooks favored Corrales going into that fight. Not that it matters much here; Mayweather would have had his way with Navarrete, and the prime, devastating, lean, mean “Chico” would have as well.
Pick: Corrales
Featherweight: Angelo Leo vs. Naseem Hamed
Sure, Hamed was going through the motions by this point, and yes, Leo has come into his own the last couple of years. But there’s still a gap between the worst of Naz and the best of “El Chinito.”
Pick: Hamed
Junior featherweight: Naoya Inoue vs. Marco Antonio Barrera
As great as the Hall of Famer Barrera was, he had his struggles with long and/or explosive opponents like Pacquiao and Junior Jones. “The Monster” would be all wrong for him (as he is for almost anyone). Chalk this one up to some we-haven’t-seen-Inoue-lose bias if you like, but I just don’t see Barrera giving better than he takes in this matchup.
Pick: Inoue
Bantamweight: Junto Nakatani vs. Paulie Ayala
Ayala was a sharp, capable southpaw who had one great night — upsetting previously undefeated Johnny Tapia by a point or two in the 1999 Fight of the Year — and otherwise won a whole bunch of decisions he didn’t deserve. He had a streak in 2000-2001, right in that 25-years-ago range, where he went 4-0 and could have gone 0-4. Point is, I think he’s a notch below Nakatani, who is currently peaking. Ayala had a tremendous chin, so maybe he halts Nakatani’s KO streak, but that’s all he’s halting.
Pick: Nakatani
Junior bantamweight: Jesse “Bam” Rodriguez vs. Mark Johnson
It took until the 14th of 17 matchups, but we’ve found my favorite of these fictional fights, and the one most likely to make me bust out a coin to decide. “Too Sharp” Johnson was a force of nature at flyweight and still nearly untouchable at junior bantam (bantam was a different story). But all the same praise could be heaped on Bam. Randomly enough, 2000 was when Johnson was very quietly in jail and briefly inactive. Is that reason enough to pick Rodriguez? Probably not, but I’ll take any random tip in either direction I can get for this impossible pick.
Pick: Rodriguez
Flyweight: Ricardo Sandoval vs. Eric Morel
I know this is wildly inconsistent of me, but Morel would later have some serious troubles with the law himself, and I’m not going to hold them against him. The 1996 U.S. Olympian is a largely forgotten fighter, but he was ridiculously skillful in his prime, and 2000 was that exact moment for him. Sandoval fought magnificently in upsetting Kenshiro Teraji in July, but I suspect he caught “The Amazing Boy” at just the right time, and that wouldn’t be the case with turn-of-the-century Morel.
Pick: Morel
Junior flyweight: Carlos Canizales vs. Ricardo Lopez
Again, let’s not run up the word count here. Venezuela’s Canizales has lost two of his last four fights. Both by majority decision to strong opposition, but still. Against “Finito” Lopez? Even a Finito Lopez who was two fights from retirement? This isn’t up for debate.
Pick: Lopez
Strawweight: Oscar Collazo vs. Zolani Petelo
Maybe it’s unfair to Petelo, but when I think of him, I think of Lopez picking him apart and breaking him down in the Mexican great’s final fight. Even if that is unfair to the South African southpaw, his five successful 105-lbs title defenses came against opponents with a combined record of 69-23-11. The popular Puerto Rican Collazo, though not yet fully tested and proven, has a lot more upside than Petelo ever did.
Pick: Collazo
Final score: 10-7, in favor of 2000
Eric Raskin is a veteran boxing journalist with nearly 30 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 CasinoReports and the author of 2014’s The Moneymaker Effect. He can be reached on X, BlueSky, or LinkedIn, or via email at RaskinBoxing@yahoo.com.
