BoxRec

Likely been done before but not this week.

Jess Willard, the Pottawatomie Giant. In April of 1915 he stopped Jack Johnson in 26 rounds. We know what happened to him in real life, but what if, for whatever reason, he decided to become a fighting champion. He hires a top trainer like Spider Kelly or Dai Dollings to improve his skills and takes on all comers:

December 1915 Willard stops Carl Morris in 8 rounds.

1916

March - Willard whips Frank Moran in 12.
June - Willard KOs Fred Fulton in three rounds.
September - Willard wins a close decision over Harry Wills in 20 rounds.

1917

January - Willard knocks out Charlie Weinert in 5.
April - Willard stops Bombardier Wells in 3.
August - Willard KOs Tom Cowler in 10.
November - Willard again decisions Harry Wills.

1918

February - Willard puts lights out for Big Bill Tate in 11.
June - Willard stops Billy Miske in 8.
October - Willard stops Joe Jeannette in 15 rounds.
December - Jess Willard signs to defend against one Jack Dempsey on the 4th of July.

In real life Willard was an apathetic champion who didn't like training, so he was not in the best of shape on that hot day in Toledo. But might the outcome have been different if he had been fighting regularly under the guidance of a good trainer? He had a poleaxe of a left jab and could put away a guy with a dynamite right uppercut. He was huge for his day, towering over many of his opponents, and he could take a terrific punch.

Would a properly trained and conditioned Willard, motivated to do his best, have won against Dempsey July 4th 1919?

Well, he had height going for him. So there may be at least one person who imagines that's a possible outcome.

I think Dempsey clobbers him into granules first time every time, anywhere near their mutual primes.

But maybe that's just my idiosyncrasies running amuck.

Hard to imagine Willard getting past all of these title defenses. Especially can't seeing him beating Harry Wills twice.
He would not have beaten Dempsey no matter what.

He simply wasn't in Dempsey's class. He also was 37 years old by then.
I do agree with your premise that things could have been a lot different had he trained harder, and fought more frequently. He may have put up a better showing. Three years off is such a long time.

He would also would probably be thought of a little more highly historically had he had a few of those title defenses and lost the title (whether to Dempsey or someone else before that) in a less humiliating way.

Interesting topic.

As for Willard vs Wills, I'm thinking the Wills of 1916 and 1917 would be more beatable for Willard than the one just a few years later. Robert Edgren, the noted sportswriter and columnist, felt that the only reason Wills beat Fulton and Firpo was because he was allowed in both fights to hold and hit. I wish I could have been there to see myself.