Id pick Dempsey because of his speed. But Max would be a dangerous opponent and IMO a more dangerous opponent than Firpo. Who takes this?
Dempsey would be my pick, BUT he gets hit too easily and Max can punch. If this is a 15 round match and Baer is still hanging around late, the tides could turn as Dempsey was much more dangerous early.
That would mean that Max has taken the best Dempsey had to offer if he's around late. That would be an "oh ****" moment for Dempsey.
Dempsey easy. At his best Jack was the more destructive puncher, much more talented fighter. Tunney commented on how difficult it was to hit Dempsey on the button.
Gracious what a mismatch, Max was simply wide open body to head from someone who knew his game as well as Jack. Dempsey wouldn't just wade in with the respect he had for Baer's power and Jack knew how to feint, once chest to chest he would just beat Max down and I would see him landing to the head as he did with Sharkey also. Max might land also but Dempsey showed he could be hurt and still find the range for a ko.
Perhaps not an easy win, but I would suggest a decisive one. Dempsey was one of the most dangerous counter punchers that the division ever produced, and Baer was prone to being countered.
They sparred when Jack was retired and way past his prime, with Max hitting him in the midsection with such force that Jack replied that no one ever hit him that hard before. But, Prime for prime Jack would wreck him. Too fast, too skilled, too vicious, and yes, too hard to hit on the button.
If Jack performs as sloppily as he did against Firpo, he might not even get the chance to explain to Estelle how he forgot to duck.
If Max misplaces his balls as he did against Louis, he may finish the evening sitting on the floor waiting for the referee to count to ten.