I would pick Lewis vs Moorer and Byrd from his era. Usyk could beat him definnetely.Wouldnt pick it but it could happen.
I’ve got to go with Lewis,he fought in a far better era and fought better opponents than Usyk has,as well as the fact Usyk has only fought 5 Heavyweights his whole career,and soon to be 1 Heavyweight kick boxer .
I got Usyk in a close fight. Lewis never fought a southpaw or even a world class pure boxer really. I think Usyk's speed, coordination and workrate would provide the same kinds of issues for Lewis as it did for the super heavies that Usyk has beaten in this era. Usyk could land 2 to 3 shots for every one shot Lewis lands, take him out of his usual game-plan and tire him out down the stretch. Lewis would still be the overall best heavy Usyk faced though, and would have attributes that allow him to do better than Joshua, Fury and Dubois. He's a physically strong guy like Them but is better at using that physicality against smaller men than Joshua and Dubois and unlike Fury packs devastating power at any range. Got the best and most technically sound jab aswell. Early on I see them having a battle of the lead hands that's near even. Usyk I think has an easier time landing good shots on Lewis than vice versa though. I think Fury is harder to catch clean than Lewis, while I don't think anybody Lewis fought was comparable to Usyk in defensive capability, maybe Holyfield but he was a good but past his best by then. Lewis' best chance would be to stop Usyk which I don't think is out of the question. If he could consistently corner Usyk and unload to the body he could wear him down, but I think Usyk's superior stamina would allow him to survive and continue on into the late rounds while Lewis would be more fatigued from his early rounds aggression. Later on I think Usyk's jab starts landing more and with more force, he occasionally lets off a fast two handed combination, and he might buzz Lewis a few times with his left. He maintains this success up till the end of the fight to win a close but clear 7-5 type decision.
Usyk wins. Lewis never fought a southpaw, and was there to be hit, didn’t have the best defense, was KTFO twice by lesser men. Usyk would pick him apart.