I favor Charles' resume at heavy. He figured out sluggers and cuties, top flight athletes and active, well-practiced operators at the highest level. Meanwhile, Jack's resume seems largely to be constructed by opportunistic matchmaking. Late 40's Ezz takes him decision after surviving some shaky moments.
IMHO: A Prime Dempsey, from 1918-1921, would knock out Ezzard Charles in the middle rounds. Ezzard was skilled, and his style could trouble Dempsey for a while, so Ezzard could make a fight of it before the knockout. Dempsey would just keep coming and get to Charles, sooner or later. Mid rounds would be my guess but it could happen sooner.
