The Only chance Charles would have in a fight with Bowe is if Bowe is the lackadaisical and out of shape version of himself the last few yrs of his career. Other than that Bowe if in or close to prime would hurt Charles badly, possibly ruin the rest of his career. Of all the "super heavys" that have popped up during the long history of boxing,and especially the last 10-15 yrs Bowe showed (Me at least) the best skillset. Bowe had all the ingredients (Other than dedication) to have ruled the heavyweight division for years, and should have been in the conversation for top ten heavy in history, possibly top 5. He had all the tools, but his lack of dedication cost him dearly.
I put the Holyfield I Bowe up against most of the top ten ATGs...and winning over at least a few of them. I don't think Lewis, either Klitschko, Dempsey, Johnson, Tyson, Patterson, or Liston could have beat him. I always felt that if that Bowe had been around five years earlier Tyson would have lost his belt before Douglas.