I think prime for prime it would be a good competitive fight but I always go with the "greater" fighter in these situations so I think Charles would find a way to win. Quarry is always fun in the mythical matchups but the thing that makes it so hard to pick him was his ridiculous inconsistency. In his biggest fights he almost always fought the wrong fight. That says something about his mental makeup and that has to be figured when matching him up against an all time great.
Would Charles really have to "find a way" though? The weight disparity is only going to be about ten pounds. (185-90 vs 195-200, prime for prime). Quarry was almost exactly the same size as Walcott. I guess you could say Charles was fairly old by the time he moved up to heavyweight, and Quarry's "natural" weight was maybe twenty pounds greater rather than ten, but what else is there in Quarry's favor?
Quarry wasnt just naturally bigger, he hit harder, took a better punch, and had terrific skills when he actually used them. You use Walcott as a comparison for how Charles could handle Quarry but Charles wasnt exactly dominant over Walcott and ended up getting KOd in one of his two losses to joe, by a sneak left hook which Quarry was good at landing himself. Some might argue that Walcott was better than Quarry but I dont agree. He was just as inconsistent as Jerry if not moreso. Like I said, I wouldnt pick Quarry over Charles but I also wouldnt be shocked if Quarry beat him. Pat Valentino wasnt as good as Quarry in any sense of the word and he fought neck and neck with Charles when Charles was as good as hed ever be at HW so its not inconceivable that Quarry could win. A big factor would be the distance. If it goes 15 Quarry's chances drop IMO because he had didnt have great stamina.
Quarry barely lost to Ellis and did so with a broken back (one round on two cards the other way and Quarry wins). But that logic cuts both ways. Quarry beat Patterson who I think was a better HW than Charles. Regardless, Charles and Ellis fought nothing alike. Ellis was a lot more mobile and a lot less willing to trade than Charles. A fight with Charles plays out a lot different than Ellis.
I didn't mean to imply that Quarry is by any stretch hopeless here, it just seemed a little odd to me that the default assumption was that Charles would have to dig deep, if indeed that was your intended meaning.
I dont necessarily think he would have to dig deep but I do think he would have to be on point to beat Quarry but I think Quarry would have to show up in perfect condition, with a good gameplan, focused, and ready to execute. Quarry rarely combined all of those things in his big matches. He was an emotional fighter who was easy to get untracked and I think this was his greatest weakness and a weakness that Charles, with his poise and experience, would be able to exploit. Its why I pick Charles. But, and its a big but, if the best Quarry showed up and fought the best Charles I think it would be a good close fight which could go either way. Charles was a much better fighter in terms of overall greatness and P4P status but at HW he was a good champion but someone I could see losing under the right circumstances to a lot of guys who probably werent as good as he was.
Eras aside Ezz cops a UD. Cutting Quarry in route to a stoppage? Maybe. Jerry decking Ezz in the fight? Maybe. When the hand is raised at the end it would be Ezz's.
Good matchup and let say the rejuvenated version of Charles of the Wallace - Satterfield-Marciano 1 fight. I think Charles by a close UD, Quarry could punch and take a punch and goes to the body well but Charles finds angles and fights inside and out counters well and trades sporatically. Charles wins without making it a war but some good exchanges- Charles quicker on the counter and enough power to keep Jerry respectful