Somehow in hindsight it's very easy to gloss over the flaws of guys like Mercer, Morrison, Ruddock, etc. I'm not disrespecting your view in any way shape or form, those guys were very solid fighters, but I'm just saying it's not like they didn't have their off nights just like today's crop of heavyweight contenders. Looking back on guys like Morrison it's easy to recall his big wins and how exciting of a fighter he was, but it's harder to recall the real troubles he had with mediocre fighters that nobody thinks are good, like Michael Bentt or Joe Hipp.
I think if we are to compare these guys we should probably compare certain fights to emphasize points for and against those contenders, eg I think Lamon Brewster could beat Tommy Morrison just based on Mercer-Morrison or Morrison-Bentt and Klitschko-Brewster I, but on the other hand I also think Morrison could outbox Lamon given Morrison-Foreman and Brewster-Lyakhovich. If you look at a whole career in an unbiased fashion you will have ups and downs and on some nights Ray Mercer should have been THE Heavyweight Champion of the world and on other nights he would be lucky to be considered a contender. The guys today can only fight who is in the division at the time, they shouldn't be judged against anyone else until their career is over or like Wlad they are a champion...then you can compare a little more fairly.
But it's ok to form some theories as to how ____ would do in today's division. I find myself wondering how Joe Mesi would handle a lot of these guys. I think that guy, although no great shakes as a pure boxer, was a very entertaining fighter and he was a very good puncher. I think he would have fallen short of a title but he would have given his all for it, it wouldn't have been some wasted opportunity. I think he would pair up well with a lot of the smaller heavyweights but perhaps Eddie Chambers gives him trouble. The bigger guys would crush him, he was too easy to hit. Mesi vs Povetkin or Boytsov would have been classic brawls (not comparing them to any of the all-time greats but the styles these guys have/had would have been great to see)!
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