Here is one thing about prime Wlad: No small guy ever beat him. Wlad wasn't in his prime against Corrie Sanders or the other randoms. But Wlad absolutely feasted and destroyed any non tall HW. Even a guy like David Haye who was the fastest HW champ we saw in years got smoked by Wlad. The jab was unbeatable and if you tried to get inside Wlad would clinch you quickly (dirty but effective). Wlad also had the most devastating left hook of all time IMO. Would current Usyk be able to beat the GOAT against small fighters?
Usyk finds ways to win against guys who should beat him. Wlad used to find ways to lose to guys he should beat.
I think Usyk is the more flexible, creative and natural fighter from the two of them. But Wlad had the more refined gameplan and in my opinion Usyk would find that his amazing lateral movement would not work as well as usual against a bigger guy that steps back in response to a side step. We can actually see this to some extent in the Fury 1 fight where Fury stepped back and caught Usyk with uppercuts when Usyk chased. On the other hand Usyk is rumoured to have given an older version of Wlad a tough time in sparring. I'm inclined to pick Wlad over the two of them but would not be very surprised if Usyk found a way to deal with Klitschko in an unexpected way.
Vlad is sucking air hard by the mid rounds due to Uysk's constant movement and pressure. He takes over and beats Vlad in a similar manner to his fights with Joshua.
Wlad would have created some new and different obstacles to Usyk as he was a dirty fighter with a very good jab, in which it would be interesting to compare Wlad's jab to Fury's. But, I think Wlad was a bit too predictable and Usyk would find holes in his defence to get the victory on points, could see a late TKO for Usyk.
This could have played out like Wlad vs a Prime Povetkin. I wouldn’t be surprised at all if Wlad found a way to nullify Usyk on the inside and got the UD. Wlad loved to fight against smaller guys his jab and his grab style on the inside would have suffocated Usyk.
Ever watch his fight with Lamon Brewster? He essentially was completely gassed and couldn't continue. Vlad fought at a controlled pace and behind his jab. Uysk uses more feights than any heavyweight I can remember. He puts tremendous pressure on opponents with his constant movement. Sure, Vlad could catch him with an uppercut but too me it's more likely that Usyk stays upright takes Vlad a part as the fight goes on.
Wlad became very adept at fighting southpaws under Steward. He would neutralize Usyk’s offense and slow the pace down with clinching. Then knock his lead hand down and land straight rights, eventually scoring a couple KDs en route to a UD victory.