Originally Posted by McGrain
If you were having an educated guess?
Assume Jack is out of the picture, for whatever reason.
Dempsey loses to Wills in his second defence, fighting Wills instead of Brennan, December 1920.
Considering Jack Sharkey was, from the reports of their fight, beating the crap out of Wills when Wills was DQ'd, I guess it would be him. And Tunney may have as well, as Wills declined due to age.
But a prime Dempsey would have had a very good chance to beat Wills. From what I've read, contemporary opinion, even from those who clamored for Wills to get his (deserved) title shot, was that Dempsey would beat him.
Dempsey would probably not have been surprised by anything Wills did, having often sparred with Big Bill Tate (one of his prime sparring partners) and George Godfrey and, by all reports, getting the better of both of them consistently. That's not to say Wills might not have won, but it wouldn't be like Dempsey had never been in the ring with anyone like him. Godfrey was a monster and Tate had some wins over some famous fighters, including Wills and Langford (although he also had losses against those guys).
All that having been said, it is a crying shame that a legitimate contender like Wills could not get to fight for the title. He certainly should have been able to.