What's your pick? Not an easy judgement to make this, so let's just have your best guess. 15 rounds, prime for prime.
At what time, their careers did not overlap ? Prime for prime, who knows ? Based on styles you would imagine a prime Jeffries would eventually take him out. Great as Wills might have been, and I believe he was great, he would not be fighting a shopworn, 5'6", half blind, blown up light heavyweight. If Jeffries was anything he was tough as nails, durable, strong as an ox with a heck of a punch and tremendous condition. If he had any of the reported speed it would not match up well for Harry.
People rarely give a current contender a chance over a past great, no one gave post-Leonard Duran much shot agains the best LWs, so I think we can take contempory opinions with a grain of salt Wills certainly became a more seasoned experienced veteran. Both men were victories over older greats of their era, whether Langford, McVey, Jeanette or Corbett and Fitzsimmons. But Wills is more tested against a greater variety of fighters over a longer period
All fair observations. I would probably still pick Jeffries and a large part of that would be how highly he was regarded head to head when he retired. When you don't have much to go by that might have to be the decider.
Hard to say how it would play out. I have specualated that Jeffries might have done well against bigger heavyweights due to his speed relative to other fighters his size. What limited information I have about him sparring with and fighting larger oponents backs this up.
Yeah, weirdly i've got Jeffries to perhaps outspeed Wills early and Wills perhaps using his superior experience to change the fight, take it inside and lose a very hard, tough fight based upon his poor start with many of the later rounds hard to score.
On the other hand Jefffries wouldn't be fighting: A 36-year old former middleweight who hadn't had a fight for two years (nor the same guy when he was 39) A former champ being almost ten years past his prime who hadn't won a fight for 6 years (and who still was able to extend Big Jeff for 23 rounds.) A 5'8" sailor who managed to go 45 rounds with Jeffries despite giving up about 30 pounds. With the limited footage available of the two, it's pure guesswork. I suspect however that boxing improved during the 15-20 years that separated their prime years. Jeffries furthermore wasn't used to fighting men his own size, in contrast to Wills. Therefore I'd favor Wills especially if it's a 15 round fight
I can't see Wills stopping Jeffries,so he has to outpoint him ,which he possibly is capable of,my nagging question is does Wills have the stickability to hang with Jeffries? Jeffries is somewhat unproven against big heavies ,apart from Ruhlin,my gut feeling is ,he would be able to handle them, but it seems illogical to expect him to get them out early when ,much smaller, older men stayed in there so long with him.And,often had him looking like a piece of raw beefsteak at the time of their demise. So,can Jeffries lay enough leather on Wills, who,was a real heavyweight ,and force a stoppage ? Or,does he risk being outboxed,by a man who ,more than matches him in size,and,probably skill?