Dempsey KO 1. If Corrie Sanders can level him in 2, Manassa Jack would tear his f....kin head off and his non-pumping heart out and eat it.
Dempsey ko 1. Dempsey is much bigger, faster, has more power and probably a longer reach too. Oh wait, I forgot I'm not in fantasy land. Wlad wins easily.
Some things changes over time, and although boxing technique seems to have stayed pretty much the same over time, athletes are better today. Not because they are more talented, but because of superior training, nutrion and drugs. So both as they were, I'll have to go with Wlad. That does not mean that it will be an easy fight though, no improvement in training, nutrion or drugs will help you if Dempsey manages to land solid on your chin enough times. So there is always that possibility. But if you match up two great fighters from very different eras, more times than not, the bigger, stronger modern guy will win.
Dempsey would win, and then his detractors would say that Wlad was just an unskilled uncoordinated oaf, so his size didn't count.
Sanders beat Waldo 7 years before 2009, the date mentioned in the OT. Jim Flynn KO'd Dempsey 2 years before 1919. So, it would be much more pertinent to mention's Dempsey's KO loss to a wild swinging, sawed off heavy on a huge losing streak.
I have to say Vlad by UD or TKO,,,,pound for pound I would take Dempsey but Vlads size and power would be a great advantage over the smaller Dempsey.
I actually think that this is a pretty good fight. If Wlad hits him clean, i think he knocks him out. Likewise for Dempsey. I see both being very cautious, which could lead to Wlad dominating the action. Dempsey was catchable, as Firpo showed, so a Wlad KO isnt out of the question. For mine, the real question is whether or not Dempsey goes into his shell when Wlad lands. REalistically, i cant really think of any other time he has done so, so it is hard to rely on this happening, just because fighters who are not as good did so when they fought Wlad. I cant think of any time where Dempsey went into his shell and stopped swinging, not even the Tunney fights, so you would have to say that he keeps the strong punchers chance right the way through. In all honesty, i dont think you can really rule out a single possiblity in this fight. Early KO to Dempsey, Early Ko to Wlad. Late KO to either, or even a points win to either. Looking purely at resume, i think that Wlad might even have the edge, although Dempsey certainly does have the more fearsome short term run. If forced to pick, I go with Wlad on points after surviving a late scare.