Jess Willard stops aging as soon as he wins the title from Johnson. He also becomes impervious to the long-term aftereffects of getting concussions. He decides to remain in boxing. Despite being a rather difficult sort of guy, Willard continues to learn and train -- fighting contenders from time to time to keep the electricity on -- until Ali gets the title from Liston. Willard challenges Ali for the title. Ali accepts. Willard by now is still in his physical prime, despite approximately 50 years of boxing experience. Who wins? Why?
Would have lost to a numbers contenders who would have turned his electricity out long before Ali would have got hold of him.
I agree with this. However: Even if he has a Tye Fields / Butterbean type career between Dempsey and Ali, that's a whole lot of boxing experience. Much more than anyone in history, despite his late start. Also, even the original Willard was good enough to stay a fringe contender in most eras between Dempsey and Ali.
Willard’s biggest problem after the Johnson fight wasn’t just his age, but instead his lack of motivation. Lack of motivation after achieving success is often one of hardest obstacles to overcome. Even Ali after becoming champion strated struggling with getting motivated to keep fighting. This was especially true when Ali regained the title against Foreman. So even if Willard stopped aging after beating Johnson He’d still get bored with boxing after a couple more paydays, so Willard would quit boxing long before an Ali fight could ever happen.
The smartest man wins more often then not. I think, though they may not look "intelligent" in the ring. Who could be more intelligent then a man with 50 years of experience and no psychical clock? Might be an immortal develops his own ways, might be he tries all manner of things and learns exactly how to fight everyone. His bodily gifts never held him back, legendary stamina truly. He'd wash Ali with ease when you give it some thought.
A better matchup might be Jimmy Ellis or James Quick Tillis. Any version of Ali before the Spinx loss toys with Willard. I would pick the Ali of the Wepner fight to pitch a shutout.
Ageless Willard destroys all!! No. Only kidding. Ali up to his very last years finds a way to beat him. By the Spinks fight maybe Jess could get a decision. Mauls him around. He'd lose the rematch tho!
Impossible question to answer. If he stuck with his style he's have had innumerable beatings by the time he faced Ali. On the other hand if he consistently learned as time went by he might be a kind of Wlad Klitschko with an iron chin and he'd wipe the floor with Ali. All I can say for certain is Willard as we saw him against JJ would have gotten shellacked by Ali no matter how many rounds you make it.