Prime to prime I don't know but I do think a 36 year old Klitschko would beat a 36 year old Ali. If they were both still in their 20s as far as age goes probably Ali's chin, stamina and speed make him victorious but as they age Ali's athleticism is no longer superlative and his less developed boxing skills start to show against more skilled fighters. Ali had trouble with Ken Norton who is somewhat like Wladimir Klitschko.
Ali was by far the better boxer but Wlad could win by KO. If I was betting money, I would bet on Ali.
Ali at the press conference: "Wladimir may hold, but I won the gold!" "Klitschko's a leaner, but it just makes me meaner." "His jaw is like glass, and I'm just too fast, but if Wlad keeps insistin' , I'll do him like Liston." Rumble, young man, RUMBLE !
Ali's not nearly as effective when he's forced to be the aggressor, which he'd have to do in this fight. Wlad's not going to gas himself out, and he's not going to fight stupid. People can get as pissed as they want to about it, but it'd take the very best Ali to win against Wlad,and if it's the older, post-FOTC Ali, I feel quite confident that Wlad wins. It's not a good style matchup for Ali, especially once he started taking more punishment in his career and relying less on his movement. Or is this Wlad vs the Ali myth where he somehow beats every Heavyweight in history by name value alone, instead of Ali the boxer?
Ali... He'd set a pace Vlad can't match... Vlad couldn't keep up with Ross Purrity.. Vlad doesn't throw enough punches....drags his jab...and keeps his feet too far apart,which limits his defensive options... Vlad isn't tough enough and lacks stanima..