Vitaly's the one who would be able to hold his own against virtually any fighter from any era due to his chin. Wlad on the other hand would be blown out inside of three rounds by nearly all the all time greats who possessed power due to his lack of chin.
Vitali's skill is based on his size and his awkwardness...Wladimir is probably the most technically skilled fighter out there right now not named Mayweather. He does everything correct and I don't know of anyone else who is more effective on the attack than Wladimir fighting these days....maybe Pacquiao but hell Manny has been outboxed several times before and I have rarely seen Wlad so much as frustrated with an opponent's boxing skill...maybe vs Brock or Thompson but he caught both those guys pretty good.
Vitali can get frustrated a little easier IMO, when he's fighting a guy who won't open up like Byrd or Johnson and he wants to land a homerun punch he gets frustrated. Wlad is smart enough to either stick with what works (even if the fans don't like it) like vs Sultan or find a way to get a stoppage like vs Brock and Thompson.
I am of the mindset that current athletes in most instances compete at a higher level than athletes from 20-30 years ago. I think current athletes can take advantage of modern science (nutrition) and training techniques and in many cases start at a younger age. Also, there is way more money involved now so everyone trys to be a professional athlete for the most part (starting in grade school) and you are closer to having the very best people at the top of the game. When I watch videos of some of the fighters from the 70s, 60s, and even 80s etc their technique is terrible and it reminds me of a bar room brawl. You stick those guys in with a guy like Wlad who has great technique they will get killed.
I think Wlad would beat any of the past fighters most of the time if you plucked them from the past and stuck them in the ring with Wlad. Now if they had access to the same resources Wlad has had for the last 20 years than maybe they could compete but who knows it is a different game now......This is IMO.
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