Resume doesn't win fights in itself. But if someone looks great, but doesn't produce the results, it's silly to expect them to do any different because it's hypothetical.
Andy can punch with a puncher and has quick hands. In a pure shoot-out it could go either way. I don't feel that Jack has a great Plan B. With Andy, just his experience with better fighters than Dempsey beat will show him the way to a decision. But, Andy may have just been a one night wonder. I'm curious to see if he is done or not.
Way too small, they didn’t have access to the medication and supplements fighters of today take, they have an older slugger type style and they are less technically sound. A big world class 240+ lb man goes through a 188 lb Jack Dempsey like a laxative and I’ll hear nothing else about it, it’s foolish to think he could be a world champion in today’s era. People gonna continue to hype them up though and say if they were alive today they’d rule the division. Jack Dempsey more than likely wouldn’t beat guys his own size like Canelo, Beterbiev and Ward never mind today’s big heavyweights. Honestly it’s like backing Rod Laver to beat Nadal. They didn’t even use the same boxing gloves back then either.
Because they weren’t good. Modern Boxers are much technically better and much better athletes physically.
I haven’t got the divine knowledges to give a breakdown on every fighter from the 20s but whenever I see the old black and white footage of old timers fighting from the 20s and 30s I’m just not that impressed, they look far less technically sound. Often it’s both guys just throwing the kitchen sink at one another, not caring about getting hit. Not all of them of course did this but yeah I think you’d have to pretty daft to back them against modern day elite fighters their own size never mind against men 60 + lbs heavier. Dempsey would not live with any good heavyweight today.