Based off their actual fight where a 10 year past his prime Holmes was able to win rounds against a prime Holyfield and be competitive in rounds he lost, I think Holmes may be the Ken Norton to Holyfield's Muhammad Ail. Give Holmes his old hand speed, legs, and stamina back, I see him winning 8-4 in a competitive fight. I just can't pick Holyfield given the evidence we have on film. Remember that even when it got up close and mean -- actually, especially when it was up close and mean -- Holmes was outfighting Holyfield and getting the better of the exchanges. Holmes was way better up close than he's given credit for. He wasn't a good grappler, but in the pocket, he was damn good, even as an old guy. edit: their actual fight was competitive enough that if they'd had an immediate rematch, Holmes might have had a shot of edging out a victory. His big problem was stamina there. If he slimmed back down to 220 or so, then went to live and train at high altitude (and really, really busted ass with cardio up there), maybe he could have eeked enough out of the tank to do it
Holyfield decisively. That is, if Holmes would even consider taking that fight when he was champ. Very careful with the belt. Not at all careful after he lost it though.
Holmes did well as an older fighter, he could do much better with younger legs, stamina and reflexes. That being said Evander at his best is no easy night for anyone. In fact if you think about it Evander is Holmes best opponent but the reverse is not true. Larry could win, I would say it’s a tossup.