Wills Turned Down $5000 Chance To Spar With Challenger Dempsey In 1919

Dempsey lived the high life, after he went Hollywood, he had his nose reshaped, hob nobbed with Fairbanks, Rogers etc and generally had a good time for three years.
Wills was a health nut who lived a spartan life, fasted regularly , and went on long hikes. Your question makes as much sense as comparing Ali or Johnson at 38 ,with Lennox or Vitali.

 

Wills was the number one contender for a significant part of Dempsey's reign.
That he deserved a title shot is beyond dispute.
Why he did not receive that shot will be argued as long as whether Ali could have beaten Louis.

Wills was no journeyman ,whether he was as good as the trio of coloured fighters that preceded him is another question.

Wills may have been fortunate to get Langford /Jeannette/McVey just as their suns were setting, if so he was equally unfortunate to come along when the aftermath of the Johnson/Jeffries race riots was still fresh in memories.
Let them fight each other , but keep them away from the title seems to have been the case.

Wills was criticised for the calibre of some of his opponents in the 20's , he was described as , "feeding on a diet of well chewed meat".

Paddy Mullins undoubtedly did not want to take any chances with his aging tiger , gambling perhaps on public opinion eventually forcing Dempsey into a defence against the Panther.

If this was the case it backfired disastrously.

Wills did not fight Gibbons, Godfrey or Tunney ,it should be said that he had already earned his shot , but if he had beaten one of them the pressure on Rickard/Kearns/Dempsey would have been almost impossible to shrug off,imo.
Mullins repeatedly turned down Godfrey and Tunney,I don't know if Gibbons brainstrust were prepared to put him in with Wills, possibly not.

Whether at that stage of his career, he would have been the winner in any one of that trio of contests is a moot point however.
From January 1922 until October 1926 [when Dempsey lost the title], Wills best win was a dreary points dec over Firpo whom Dempsey kod in 2 rds flooring him multiple times.
If Wills did box under wraps against Firpo,as some one has suggested ,he may have done better to take a leaf out of Jack's book and go all out to make an emphatic statement by taking the Argentinian out early,and rasing his profile with the paying public.

Fact is Harry got shafted, who is to blame?
Maybe all the cast have some degree of culpability in the affair?
Rickard for bowing to political pressure,Kearns for using that excuse to sidestep a dangerous challenger, Dempsey for being led by the nose by both of them.

Dempsey's autobiography reveals a hesitant man, surprisingly deferential to both Tex and Doc.
I don't find it a stretch to believe he was manipulated by those two button pressers.