Who wins?

I pick Tyson by brutal KO..

I think Tunney was a great defensive fighter with a rock solid chin and underrated stamina but he would have likely gotten stopped early by both a prime Jack Dempsey as well as a prime Tyson.

I regard Tunney as the best boxer of all time, and he is one of my personal favorites. But against a prime Tyson, he would most likely be overwhelmed and knocked out. An ageing Dempsey caught and hurt Tunney in their second fight, and therefore I have to belive that Tyson could do the same. Tyson puts Tunney on the canvas for keeps inside of 4 rounds.

I'd pick Tyson by midround Ko