Dempsey is faster and more relentless than Beterbiev. Beterbiev is still somewhat risk averse when facing a high caliber guy while Dempsey was relentless and slightly less technical. IMO prime Dempsey beats him by a decision aka Gibbons or by a late stoppage.
I think that Dempsey's fast start combined with Bivol's late fade under Dempsey's pressure would be enough to get him home over 10. Bivol would do less well over longer distances.
Bivol isn't a dangerous puncher though. Beterbiev, like GGG, is highly technical and perhaps too technical at times. Sometimes you need a bit of wrecklessness. Dempsey had a good chin (one stoppage in God knows how many fights) and regularly took hits from 200 plus pound guys. I don't see Dempsey fighting a highly technical fight like Beterbiev. Dempsey, despite whatever his flaws was, was very very fast. I don't think Bivol has the speed to stay out of range and nor does he have the power to intimidate him.
Bivol hits hard enough to earn his respect and Jack could get sloppy, especially when things didn't go his way early. Tunney slapped Dempsey around unmercifully at times, even putting him on the canvas. It would be a very interesting fight.
Yes i can see it being competitive for sure. I do think Bivol wins some rounds. But peak for peak, i see it going one way. Interesting for sure.
I think fluid, defensively responsible movers with good jabs like Tunney and Bivol are always going to be nightmare match-ups for Dempsey.
I'm a big Dempsey fan, but Bivol like Tunney has a very high boxing IQ , Dempsey if he couldn't really land something that changes the fight early he's going to struggle to outbox Bivol to win a decision. But I'd still edge Dempsey
A bunch of Old Timers? Wharfbrawlers and lightheavies? Guys who went straight off the breadlines to the arena? Pass.