Even if you think they have a 5% chance, who would be the top 5 hardest matchups for Usyk pre-1930? Here are my candidates, though admittedly mostly theorietical due to lack of footage; 1. Dempsey (genuinely interesting fight for like 4 rounds, Dempsey’s fast and would be a stylistically unique fight for Usyk. So explosive and aggressive, good body puncher, great infighter and who knows how those blows would tell under 5-6 ounce gloves like in Jack’s era. Usyk’s the comfortable favourite but it’d be intriguing for the early half) 2. Sullivan (probably the most meme’d pick on here but hear me out; Sullivan’s speed, explosiveness and early round workrate was compared to Dempsey’s, the quality of his right cross was compared to the likes of Benny Leonard and Joe Gans which is a great punch to have against a southpaw) 3. Wills (roughly the same size as Usyk with a longer reach. We don’t have footage of prime Wills but he was described as well rounded, strong, and quick which he also is in the training footage we have of him) 4. Goddard (who was described like a freight train in terms of aggression and power, reading about him kind of reminds me of Chisora. Maybe if he was a bit bigger it’d be more competitive) 5. Jeffries (he was clueless when his opponents moved but he also had some pretty accurate body punching so if his chin holds up who knows) Who would your picks be?
That’s an interesting question. I don’t claim to be an expert on every 1920s boxer, but looking at the archetype of that era, the technical gap is the biggest hurdle. Honestly, I don't see anyone from that period beating Usyk at range. His footwork, distance control, and lead-hand manipulation are products of a modern style that no one from that era would have any real knowledge of. No heavyweight from the pre-1930s era would have an answer for the angles Usyk creates if they just fought him at range hence why I don't think someone like Tunney would ever beat Usyk. The only fighters who stand a chance are those who can wither his volume, get inside, and bully him. While Usyk is great at clinching and pushing off to reset the distance, he isn’t a great inside fighter. To beat him, you’d need someone who can physically muscle him around. The struggle with that is that while Usyk is a small heavyweight today, he would be a massive heavyweight by 1920s standards. Most legends from that era, like Jack Dempsey, often weighed under 195 lbs so Usyk would actually be the one with the physical advantage against most people. So, if you can find me a fighter from that era who: Matches Usyk's physicality Has the chin to walk through his distance fighting Can force a 'phone booth' fight to nullify his feet. then you might have a matchup. But without that physical parity, Usyk’s modern technical toolkit is just too advanced for that era to overcome.
Dempsey would be very challenging for Usyk. A quick fisted and relentlessly aggressive opponent that had the foot speed to keep Usyk in front of him, and was adept at fighting from different angles. Also Dempsey's endurance was superior, with Usyk usually slowing down around 6-7 rds. It would be very challenging for him to keep pace with Dempsey after about ten rounds. Especially for 15 rds....
Depends on the ruleset and equipment as well, especially for guys as early as Sullivan. Usyk would have a lot more trouble with pre Walker Law stipulations and referees. Fighting a guy in early Queensbury would be a bit different to nowadays, and LPR would be totally different. With current rules and equipment he beats them all clearly imo.
