Tunney beat Dempsey in 1926 & 1927. Tunney was about 29 & 30 yrs old for those 2 fights, and Dempsey was 2 years older. Films appear Tunney just had the great style to beat Dempsey, and the 2 actual fights were scheduled for 10 rounds each. Would Tunney just have always won if they had fought several years earlier?
Honestly it's possible. Tunney was damn good. Whatever you think of him out of the ring, in the ring he was such a smart, good fighter. Based on what I observe in their first fight versus their second, I favor Jack the further back we go. We don't have early footage of Tunney like we do with Dempsey, but I assume Gene would've been a problem at any time.
You could certainly get a Dempsey win if you went back far enough, because he peaked a lot earlier. Judging where exactly the intersection lies is a bit harder. Dempsey had difficulty motivating himself as champion, and put on some very sub-par performances long before he met Tunney. Even so, you look at the Gibbons fight, and it is easy to imagine him being too much for Tunney even then. Anything before 1923 and you are going to be matching a very green Tunney, against a very good version of Dempsey.