Buster Douglas was very much like a Jack Sharkey type of fighter. On his best night he was outstanding, such as the Mike Tyson fight, he utilized his jab, showed amazing heart, quick combinations at times and crisp straight shots, but he was very erratic and very inconsistent, much like Sharkey himself. But on his best night he would give Larry Holmes some trouble no doubt, I think he'd give pretty much any heavyweight trouble on his best night. I don't think either has any real stylistic advantage over each other, so it would be a pretty competitive fight. However, I'd take Larry by stoppage in the end. Like I said I think it would be pretty competitive up till then, but Larry firmly in control. Even though Buster had a reach advantage and a very good jab, Larry had probably the best HW jab of all-time, and Buster's need going to be able to adapt the stick-and-move style enough to beat Larry, a rangy out-boxer with an ATG jab and the best footwork since Ali. Everything Buster does Larry just does that bit better, plus he has a better chin. Larry had under-rated power aswell, very good overhand right not to mention his right uppercut, I think they'd be trying to outjab each other with Larry having a bit more success, and landing the cleaner bigger shots and eventually wearing Buster done to a stoppage, probably after a few one-to-two shot knockdowns.
The jab would be one of the deciding factors. But Holmes did struggle with large men who had good, long jabs during his career as well.
Could look a bit the Holmes fight against Carl Williams. Douglas does have a good jab with good reach but as has been mentioned I don't think that anyone get's past Larry's jab at his peak. Holmes also threw more combinations then and was very agile on his feet. I think Holmes would win on a TKO or a wide UD.
It can be hard to chose, the Douglas of the Tyson fight was great but it was a once in a lifetime performance, I have to go with Holmes by UD.
Douglas did fight the perfect fight against Tyson, and when he wanted to he just about did everything better than Holmes....but I think Holmes 9/10 would beat Douglas, because, you never knew when Douglas was gonna come in serious, while Holmes was always in superb condition and didnt over look nobody...I think it goes the distance every time, but Holmes wins.
While the best version of Buster was something special, this is predominantly a boxing match and that means Larry Holmes for me, sure Douglas can get rough, very rough, but Holmes can handle himself here imo.
Douglas had more than one great night. Both at their absolute best...well you would be inclined to pick Holmes. But consider something. Holmes was at his very best when his jab was working....not when it was neutralized. Douglas had a jab that was just about as good as Holmes...and that isn't a wayward assertion. We are after all, talking about best versus best here. Tim Witherspoon handed Holmes all kinds of trouble by neutralizing Larry's jab. Ditto with Carl Williams. This would be a fight based on sheer style and one fighter's underrated ability to trouble the strength of another fighter. In the end greatness would prevail...but at that point it would be a tactical, difficult dogfight.
Douglas was at the peak of his powers for only one fight, where all forces conspired to grant him that one win over a slipping Mike Tyson. Based on that alone, it is difficult to predict what will happen between Douglas and Holmes. I find it appropriate to echo what others have already said about Douglas' great size and jab, and how that might contribute to a win for him against the Pennsylvania man. However, he himself had trouble with the jab if we're allowed to take the Tucker bout in as any kind of indication. Over ten fights, Buster might win one or two, but probably none.
I'd say Larry Holmes takes it via late TKO or a close decision. I'd also go a step further and liken the fight to Holmes Vs. Cooney. On his best night Buster Douglas would look somewhat like Cooney in style, but Buster would be much more effective then what Cooney had to offer. Faster jab, better footwork, better head movement, and a lot more control of the power punches through good combinations. I always thought Cooney was great at the basics, but extremely limited outside of that basic skill set. Buster had a load of natural talent, but he also had the unusual ability to give up. I thought when Buster took on Tony Tucker, he had more of a chance of taking that fight, but he just lost all his heart and momentum*. Larry knew just how to control a fighter in the ring. Great footwork, excellent jab, and a whole lot of determination. This might turn out to be a much better fight then I once speculated it to be. *I think the cards were split three different directions. One a draw, one for Tony, and one for Buster.
Holmes was simply in a higher class and while Douglas had some decent abilities, everything that he did, Holmes did better.