With the amount of time that we, as boxing fans or boxing writers, spend sitting around pondering dream fights, staring up and down divisional rankings trying to come up with pairings to toss out there on Twitter to spark conversation or, during a slow week, to use as fodder to manufacture a column (cough, cough), you’d think every conceivable matchup would have occurred to us.

But somehow, until I read Lucas Ketelle’s piece this Monday spun off an interview with Nonito Donaire, the idea of Donaire squaring off against Roman “Chocolatito” Gonzalez never crossed my mind.

I think I know why, though the reasons changed over time.

For most of their careers, they were at least a couple of weight classes apart. At the time Donaire left the flyweight division, where he’d won his first major title, in 2009, Gonzalez was still a strawweight, making defenses of the first title belt he’d won. By the time Chocolatito had ascended two more divisions to win a title at flyweight in 2014, Donaire was a featherweight. It wasn’t until 2018, when “The Filipino Flash” dropped back down to bantamweight, that these two extraordinary fighters were ever within one weight class of each other.

And for the last six years, that’s where they’ve been: one weight class apart. Just three little pounds. The equivalent of a couple of Zhang Zhilei’s toes.

But Gonzalez vs. Donaire still never entered my brain, maybe because they were both doing a fine job keeping busy with suitable opponents in their respective divisions. Donaire pushed Naoya Inoue harder than anyone else had en route to losing the 2019 Fight of the Year, then got back to winning belts and knocking out undefeated kids a decade or more younger than him. Gonzalez renewed acquaintances with Juan Francisco Estrada across 24 spectacular rounds and also bagged a belt and knocked out a fighter who’d previously had a zero on his record.

And maybe I didn’t entertain thoughts of Flash vs. Choco over the past year simply because I didn’t want to think about Donaire vs. anybody after his last fight.

Donaire lost a close decision last July on the Terence Crawford-Errol Spence undercard to Alexandro Santiago, a fighter a prime Flash would have flattened. At age 40, it looked like the end of a glorious road. There was no reason to picture what Donaire vs. Gonzalez would look like, because there was no reason to picture what Donaire vs. anyone would look like.

But then came those quotes he gave Ketelle:

“This is a fun fight. This is what I’m all about. We’re about the same age or maybe I’m a little bit older, but ultimately, we’ve done our job and showcased our ability throughout the years. I think it’s something that neither of us have any advantage on. I think this is something that can be a really terrific fight.

“I’m a big believer in my capabilities, and he is too. That’s why I’m saying this is a fight that needs to happen, and it will be an exciting one at that.”

Saying it “needs to happen” may be a reach, but otherwise, no lies detected.

It’s an extremely rare situation, to have two fighters at these ages — Donaire is 41, Gonzalez is 37 — who still are (or at least may plausibly still be) world-class, who are both easy first-ballot Hall of Famers, possibly in a position to square off. And the vagaries of alphabet hardware aside (there are “interims” and “supers” and “diamonds” and other such nonsense dotting their BoxRecs), these are both fighters with claims to titles in at least four divisions.

There is very little precedent for anything like this.

We can’t say for sure that Gonzalez and Donaire are at the tail end of their careers — it’s conceivable that one of them could still be going five years from now — but let’s operate under the assumption they’re each in their respective final chapters.

So if we’re looking for past fights between two Hall of Famers who were both in their waning moments but were still title threats (questionable in Donaire’s case, but ride along with me), it’s not a long list.

Lennox Lewis vs. Mike Tyson qualifies in that it turned out to be Lewis’ second-to-last fight and Tyson’s fourth-to-last (for now), though they were a bit younger (36 and 35) than Donaire and Gonzalez and, especially for Lennox, then the heavyweight champion of the world, we didn’t know the end was near.

When 36-year-old Joe Calzaghe beat 39-year-old Roy Jones and promptly retired, this would have seemed a perfect parallel … until Roy fought on for another decade.

Jones had a lot of these, actually. His win over Felix Trinidad to set up the Calzaghe fight was “Tito’s” last bout, at age 35, but again, Jones was nowhere near the end as it turned out. And neither Jones nor Bernard Hopkins was close to retirement after all when they staged their sad 2010 rematch.

The Tyson-Jones fight doesn’t count because it was technically an exhibition, though a reported 1.6 million pay-per-view buys suggest that didn’t hurt it commercially.

Kell Brook’s KO of Amir Khan in 2022 seems a fine example, as neither has fought since, but there’s one big problem: neither of those men is going to sniff induction in Canastota.

The third fight between Jeff Fenech and Azumah Nelson, in 2008, when they were 44 and 49, respectively, nearly fits the description, except neither had boxed in about a decade and certainly were not perceived as legit contenders the way Gonzalez and, to a lesser extent, Donaire are.

George Foreman vs. Larry Holmes would have offered something of a parallel had it come off as scheduled on Jan. 23, 1999, at the Astrodome in Houston, but Foreman called off the fight because the promised finances weren’t there.

And is it fair to compare this to 38-year-old Floyd Mayweather winning the richest fight in history against 36-year-old Manny Pacquiao? They were both still part of the conversation for pound-for-pound supremacy coming into that fight, so it hardly felt like either career was winding down — even though, if you don’t count exhibitions, Mayweather’s was.

There’s no perfect comp, but one thing is clear: It’s not a glorious history of great thrills and enhanced legacies when fading but viable legends meet. Of all the fights mentioned in the last eight paragraphs, there isn’t a single one worth watching twice.

And yet, I’m not dissuaded. I’m fully on board with the idea of Donaire vs. Gonzalez. It feels like the time is right for this fight that I didn’t even know I wanted before Donaire started talking about it this week.

As I’ve said and written countless times, if older boxers insist on continuing to compete, it’s best if they fight fellow older boxers. Gonzalez recently sparred with Jesse “Bam” Rodriguez, and reports were that it was a beautiful boxing ballet. But I’m not terribly interested in seeing it happen for real. Rodriguez just plowed through Estrada, and I suspect it wouldn’t go much better for Chocolatito than it did for his chief rival.

Great old boxers fighting great young boxers is usually a sad scene. When a great old boxer picks on someone his own age, it’s less worrisome.

Donaire vs. Gonzalez pairs two men who typically make for spectacular action and it does not come with a clear-cut favorite or underdog. Strange as it may seem to string these words together, Donaire-Gonzalez would be an outstanding piece of matchmaking.

In a week that saw the announcement of one of the all-time foregone conclusion fights in Saul “Canelo” Alvarez vs. Edgar Berlanga, and that saw the floating of one of the most nauseating potential alphabet atrocities in history in Jake Paul vs. Julio Cesar Chavez for some sort of cruiserweight belt, 41-year-old Donaire calling out 37-year-old Gonzalez is a welcome change of pace.

This fight exists directly at the intersection of the now and the nostalgic. We can live in the present and live in the past simultaneously. We can hope to see one last glimpse of greatness out of these Hall of Fame-bound fighters, and be glad that neither is going to take a beating from some punk half their age.

Your subconscious tells you two veterans like Gonzalez and Donaire have probably been circling each other for years, but it turns out they’ve only been circling each other for days. And neither has too many days to waste. So don’t even think about using the word “marinate.” Just toss this one right on the grill, and sit back and watch the smoke.

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, Ringside Seat, 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, and Ring Theory and currently co-hosts The Interim Champion Boxing Podcast with Raskin & Mulvaney. 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 or LinkedIn, or via email at [email protected].



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