Jess Willard vs Deontay Wilder.

Wilder by KO in the second half of the fight. Willard was likely more durable and stronger, but I don't think he was durable enough to take bombs from Wilder (and he doesn't have defense to stay away from it) and he didn't fight up to his strengths (he wasn't an infighter which could help him here).

 

I don't think much of Willard.

Then again, I don't think much of Wilder, either.

It's actually a better matchup than it seems, to be honest. We've all seen Wilder KO guys with his power. Then again, we've also seen Wilder throw everything but the kitchen sink at guys like Duhaupas without KOing them.

Willard's chin was seriously good, and Wilder isn't hard to land on, even for a low-skill guy like Jess.
On the other hand, Jess was easy enough to land on, even for a low skill guy like Wilder.

If I had to pick, I think I'd take Wilder, in a mauling bruising kind of fight where Willard lands his fair share and Wilder wins by late TKO with his face all lumped up.

 

Willard was big, tough and brave, but slow. He took a fearsome beating from Dempsey in relentless attack mode.

Deontay will largely have it his way and should be able to land enough big shots to stop Jess for the night in 5 or 6 rounds.