I think it's Douglas. He was ready for a world-class outfight, while Holyfield was probably too slow on his feet, as the fight with Lewis showed three years later (it only got worse). What wasn't a problem against Tyson moving forward was a problem against Lewis staying away and would have been a problem against JBD staying away. jab is the key. I'd rather see Douglas's Tokyo with Holyfield 1991 and I'd probably go with Evander in that case.
Holyfield still wins, but it takes longer to break him. Tokyo Tyson threw one punch at a time and his pace and footwork was much slower than normal. Holyfield threw quick, in combination, maintained a blistering pace, with quick, peppy, in and out footwork. Perfect game plan. He did the opposite of what Tyson did. Douglas was very good against Tyson, but a poor version of Tyson accentuated and helped allow and make Douglas look even better than he would have performed against the superior version. Holy and his team usually knew how to game plan for opponents. He had a plan for Tyson, executed it perfectly, and did and would have done so for Douglas.
For me the biggest difference between Holyfield and Douglas is toughness and determination. That same distinction would emerge whenever the two would meet in the ring.
The thing is with Douglas people have this misconception that Douglas only turned up for 1 fight against Tyson. I keep having to repeat this but Douglas was in red hot form between 1986 to 1990. During this period he only lost 1 fight and had notable wins vs Page, Tyson, Berbick, McCall, M.Williams. The Williams fight in particular was a stand out performance in which Douglas dropped his opponent 3 times with a jab which is unheard of. So Douglas was always showing his talent during that period. The issue is if Douglas really gets tested in a fight his suspect heart/mentality may come in to play. And there's no worse fighter to fight at Heavyweight than a warrior like Holyfield who will test all those attributes. Douglas was doing well vs Tucker but then got tired and started taking punishment and quit. Against Tyson well.....Douglas had it all his own way except for a brief knockdown so Douglas never really got tested round after round. I think an in shape Douglas would perform better against Holyfield. But eventually Holyfield would grind him down and stop him late on.
I'd pick the Holyfield from Tyson 1 to beat Tokyo Douglas, too, but being too big is strange rationale. He's shorter and lighter than Douglas, with a shorter reach.
