I will take Dempsey with Tyson close as well. Marciano could have worrn him down. Plodders have little chance. That takes a lot of the big men out, as they lose to the speed and movement. Larry Holmes cannot win because he is a lesser version of Ali. The fast moving crowders seem to do best. They have to be fleet of foot, with good head movement, fast hands and a superb left hook.....Guess who that describes.....
In my mind it would be Holmes. That jab would trouble anybody who ever stepped into a ring. I take Muhammad to win,though,by around three or four points. Ali's superior speed and right hands would seize the day for him. And if we're talking a PRIME Ali,his workrate and stamina would easily be the equal of Holmes'
Lewis and Holmes would cause him problems but Ali still triumphs.As for the rest a peak Ali wins with ease
Joe Louis IMO. Muhammad Ali had a few fundamental flaws, and Louis would not miss a change to exploit them, and he is also the goat KO artist so even though he is not as strong a puncher as a Shavers or Foreman when it comes to one shot power, he has the power,speed,precision,technique,balance,economy and killer instinct to actually finish Ali unlike the rest of the heavy punchers Ali faced. I still think Ali wins due to Louis's struggles with movers, as well as Ali's great chin. but I think Louis has the best chance.
Huge right hand, huge reach, huge left hook. Baer had fast feet when he needed them too. The best version of Baer, of course. Before the rot set in.
Pre-prison Tyson is the only one and I wouldn't be too confident with the pick, Tyson gives Ali fits though.
I'm saying Joe Louis, though the Larry Holmes of the 70s would have been very hard for even prime Ali to get past. I think Louis would have scored a knockdown...but see both Joe and Larry losing Split Decisions. In rematches prime Ali would have had it easier with Joe (UD), but probably still struggled with Holmes (SD). So, if we're talking multiple fights, Holmes would be the toughest for him imo. Single fight, Joe Louis puts up a fight not terribly far (in terms of determination, heart, and punching power) from what Frazier did in the FOTC. The only thing that would sway it more heavily in Ali's favor would be if Ali psyched Joe out, and I doubt prime Louis could be seriously psyched. I also feel that the Liston who knocked the crap out of Patterson the first time would have been a more difficult man to beat than the slightly-past-it guy who got whacked around in the two fights with Ali.