Jack Dempsey couldn't even compete at CW. He'd be a LHW at best. His dimensions are almost exactly the same as Kovalev's.
Dude, 185 6'1" Dempsey wouldn't compete at cw? Laughable post. Usyk better not move up to hw, won't compete.
Dempsey would be very competitive at CW...certainly could weigh 200 and be very very fit. But I don't see him at HW.
I think you are confusing Dempsey with glass chinned Enzo Mac? Haye couldn't handle an aged Carl Thompson. He ducked Cunningham and Adamek also.
No, not unless he wanted to give up a massive weight advantage to his opponents. 185 was Dempsey's prime fighting weight; modern day top level CW's routinely fight at 210 - 215. That's their prime fighting weight. Fighters like Usyk, Gassiev, Briedis etc are essentially small (1970s era) HWs boiling down to a lower weight class that wasn't available in Dempsey's day to maximise their physical dimensions. Dempsey at CW would be competing against huge, athletic fighters whose natural weight is a good 25lbs above his. Just imagine how Kovalev does against Gassiev for a good indication of how that'd go down. Could Dempsey bulk up? Yeah, course he could. PEDs might even allow him to retain all the speed and movement of his 185lbs iteration. But he'd still be undersized in a hugely competitive division, and quite frankly underskilled too, if his video footage is anything to go by. He'd likely consider it a step too far, and focus instead on boiling down to 175 to maintain his size and strength relative to his opposition. As for Usyk, different scenario. At HW he'd be fighting against men on average bigger, slower and less skilled than him, which would negate his size problems somewhat. Dempsey moving up to CW would find men just as fast, vicious and powerful as himself, and then some. There's nothing to offset his disadvantages.
Also, bear in mind the Dempsey that we see on film was fighting with minuscule MMA type gloves which he would not be able to wear in a modern boxing ring. That'd drastically affect his power and ability to cause facial damage.