Holmes was very hard to beat at his best. I wouldn’t pick many against him to be honest. And even then not with any real faith. But as good as he was and as hard as he was to beat, he struggled with a lot of fighters not half as good as Charles. Guys who when Larry fought them, were not much better than Coley Wallace who Charles absolutely dismantled. I have never seen Charles against Joe Baksi, another commanding win Charles had over a big 1980s sized guy who was at least as good as Berbick, Bey, Snipes etc. Then there was Elmer Ray who was just as good. So you never know. Charles was absolutely a better heavyweight than Michael Spinks. it seems a light, fast, tough guy who really could box gave Larry more problems than the big dudes.
I think Holmes would wind up beating Charles up on something of a backfoot, I think he would end up stepping out and banking rounds. Nobody would like it, i think this would not be a good fight but one Holmes would absolutely control for the second half. First half of the fight would be interesting though.