Tyson and Dempsey switch opponents

Tyson would go undefeated by KO over every single one of Dempsey's opponent's with little resistance. Dempsey would beat Berbick, Biggs, Spinks, 38yr old Holmes (Prime Holmes whoops him), Tubbs & Williams. Bruno is a difficult fight but I think he would win after having some trouble with his size & power early (he likely gets dropped & hurt). He beats Thomas too but has a tough time doing it. He loses to (Tokyo) Douglas, Ruddock & Tucker. 50/50 against Bonecrusher - but I'd favour Smith slightly due to size, reach, power & chin.

 

Tyson has the better chance of going unbeaten

 

Tyson would ko everyone while Dempsey would lose more than he won.

 

Wouldn't be that interesting for Willard when they carry him out of the ring on a stretcher.

 

True. He would struggle with all of them.

 

Dempsey looks more human and Tyson becomes an alien.

 

Tyson could finish that group off in a weekend.

Jack loses half those match-ups and it would take him two careers to do so.

 

All of these guys...

Trevor Berbick
Bonecrusher Smith
Tyrrell Biggs
Pinklon Thomas
Michael Spinks
38 year old Holmes
Tony Tucker
Tony Tubbs
Carl Williams
Frank Bruno
Buster Douglas
Razor Ruddock

 

Tyson would knock out every person that Dempsey fought in the first round. Dempsey would of been knocked out by everybody that Tyson fought. You do realize boxing has evolved since the early 1900's right? Also you do realize there are weight classes for reasons right? I know what you will say but Dempsey beat Jess Willard and he was a modern size guy. He was wasn't he? But he didn't have modern skills. Willard is so bad compared to modern heavyweights that he makes Deontay Wilder look like Pernell Whitaker.

 

Lol Jack loses to half of these guys? How about Jack Dempsey gets destroyed by all of the guys listed are natural modern heavyweights with modern skills.

 

You really don't know anything about boxing do you? Is there any real reason why you joined this forum? Lol Dempsey was a 190 pound guy which is bad enough when trying to compare him to modern heavyweights. Then you do realize boxers from the 1910's/1930's when Dempsey fought weren't nearly as skilled as the fighters you mentioned? Maybe you should stick to a sport that is easier to follow. Clearly this boxing stuff is way too much for you to handle