Sorry to say, but I would only favor him over Fitzsimmons. Jeffries would batter him into submission, Johnson would cut him up and stop him easily, and Corbett would win a decision.
For sure he could have been the champion in the period between Jeffries retirment and Johnson wining the title. I don't think that he would have beaten Corbett, Fitz, Jeffries or Johnson though.
I wouldnt be surprised if Jerry did quite well, Jefferies was given hell by Tom Sharkey by all accounts, Jerry might be able to replicate that feat or go further ? Jeff was not the fastest heavy on two legs, and if Jerry adopted the Lyle Blueprint if could be that Jerry could Matador Jefferies, and if it came to Tradeing we know that Jerry is very capable and not at all shy, but he would have to stay disiplined and not succumb to his Urges to go toe to toe with Jeff for any protracted lenght of time, Jeff probably a big Favourite but i think Jerry my suprise I definately would Fancy Jerry Over Bob Fitz, its a fight i think Jerry can let it all hang out and go to war with Fitz, if Jerry Engaged Fitz like he did Frazier in their first Fight i would have a strong feeling for Jerry James J might be something of a Toss up with James J perhaps favoured, i do not think Jerry Liked Mobile Boxers too Much, Machen outslicked him when young, Jerry Struggled to squeeze past Larry Middleton, and of course lost to Ellis, James J would have to keep on the Move but could stay a step - an - half ahead of Jerry, but he does not want to Trade with Jerry,! More through styles James J on Points, but it would not surprise me if Jerry Caught James J like he did Patterson and perhaps not let James J off the hook ? Jack Johnson i can see being Floored by Jerry, being too casual and paying the price, but getting up then getting down..to business Even Jack can not afford to take Jerry Lightly, but if he performes to the best of his ability could well cut Jerry up for a Stoppage, again Jack's mobility will not be to Jerry's liking. Jerry is the type of fighter that will, on his night give most aggressive fighters plenty to think about, that's why he matches up so well Quarry- Bear / Quarry - Farr / Quarry - Valdes / he seems to slot right in and usually makes for an intersting "what if.."
Corbett and Fitz were not champions in the era covered. I favor either to defeat Quarry at their best. Jeffries would be too strong and Johnson too everything. Quarry might have slipped in as champion during the Hart and Burns reigns, if he could get a shot without meeting the black dynamite crew, which he probably could have, given the climate of the times.
Quarry does very well in this era. With his speed/chin/counterpunching and more modern style of boxing I think he could become a champion in this time period. If Jerry can take bombs from the Likes of Shavers and win and go toe to toe with Frazier and be competitive before being stopped on cuts then I think he can hang and bang with fighters of 100 yrs ago.
Also though, Quarry would have to face the likes of Sam McVey, Sam Langford, Joe Jeannette. Quarry might have a chance with McVey and Jeannette, but I think that Langford stops a game Quarry.
The fight game was way different back then. The means, methods, lifestyle, diet, distractions and lifestyles were so very opposite. The competition grew with time as the sport became popular, with more fighters the skill level can only go up. I'd have to go with Jerry doing well against all those guys. He was no slouch.
His arms were too short. But he'd been a big heavy then....at 195 pounds...sure there were others bigger like Fulton a bit later.... I don't think Quarry could go 25 rounds. Corbert beats him, and he beats Fitz more than likly, but again here is where his short arms will hurt him...because form the waist up Fitz was a heavy. Jefferis beats him as does Johnson...He beats short but powerful Burns and Hart...McVey and short Jennette, but loses to short Langford. He beats Root no problem.