Imagine if Wilder was sent to 1919 to replace Williard and face Jack Dempsey in front of 80,000 people in Bay View Park Arena, Toledo Ohio. How would Dempsey handle Wilder? I see this quick work for Dempsey.
We can still do this 100 years later, march Julio Cesar Chavez jr. into the ring vs the Long Legged Titan & you will get the answer :smoke JCC Jr average ring weight (last 3 yrs) ~ This content is protected lbs, Height: This content is protected Jack Dempsey ring weight (vs Willard) ~ This content is protected lbs, Height: This content is protected
Size difference and Wilder being a (possibly roided) modern athlete would make him a huge favourite, although knowing Wilder it would probably still be competitive.
I think if Wilder is brave and tries to make a fight of it right off the bat he might luck out and land something big. He's got big power if nothing else. That would be his only chance. If he tried to mess around with Dempsey the fight would be even shorter than Willard's voyage, who had a good chin. Wilder can't take power. They would have to surgically extract Jack's fist from Wilder's throat.