I'm going to have to take Charles on his much better and deeper resume at heavyweight. It would be a tussle, tho.
Charles was great. [url]https://www.azquotes.com/picture-quotes/quote-roland-la-starza-was-tough-but-ezzard-charles-was-the-toughest-man-i-ever-fought-i-learned-rocky-marciano-65-61-73.jpg[/url]
Don't be so fast to underrate Gibbons .. He was much better defensively than Charles and likely had a better chin. Of course Charles was an exceptional light heavyweight but he may not have been a tougher match up for Dempsey. That said these are terrific match ups with properly sized guys .. I've often wondered where the cut off should be based on just how much bigger these fighters have become and at this point I'd say realistically 210 and under are heavyweights and above super heavyweights .. guys like Ali, Foreman, Holmes had the frames to easily be over 225 with todays training and be in top shape ..
Brilliant as Charles was, I don't think that he was really elusive enough to beat Dempsey. Also it is by no meas a given that Charles would beat Gibbons or Sharkey.
Gibbons has ZERO resume at heavyweight. The fact that he represents one of Dempsey's better pelts is both damming and revealing. Charles by latter round KO.
Again, Dempsey has very little pedigree. The fighters he beat don't amount to much at all. Meanwhile Charles has a stellar resume at heavyweight. He is the proven goods in this discussion.