The smart money could be on Holmes, but I'm going to go against the grain and pick Holy. Holmes had a tendency to fight fire with fire in exchanges, and he's no match for Holyfield in this area. Not that Holy will KO him, more that Holy will win these exchanges and they will happen more often as Holmes gets dragged deeper and deeper into a war. Holy was good on the outside, but he'd find that Holmes jab was a little too hard to get around in an outside fight only, so he'd bring it to the trenches. Making it a dogfight and get insides more and more. There he has the advantage and possibly enough to eek out a split decision win.
Holmes would probably pile up an early lead which would ultimately seal the deal. I agree that Holyfield was the better brawler, but Holmes could dish it out as well and when he inevitably loses steam in the later rounds and has to trade more I think he'd win his share too...8-4 for Holmes.
I could see Holmes wobbling Evander late being ahead in the scoring and Evander roaring back. Larry by UD 145 -141
I know Holy had a great Chin but Larry could be vicious and EH to brave for his own good . Would be such a battle that Imo Larry would HAVE to batter him to keep him from rising !
This is a distinct possibility. There'd be far more exchanging than most envisage. Holyfield isn't going to meander around content to lose a decision - he's a great fighter and very skilled in his own right. I could see a split trilogy, a great one. Both have enormous fighting heart and determination.