Why 87 Tyson beats 66 Ali...

Before entering a debate like this one has to acknowledge that proposing results for hypothetical match ups which will never take place can never be highly accurate. One would imagine that to best increase accuracy one has to have conducted extensive research into the lives and times of the fighters in question, to have reviewed extensive tape of the fights of the fighters and to have some understanding of their disposition. While extensive research for many past and present fighters is possible, for many it is not. Tape evidence of these fighters is often non-existent, or limited and of poor quality and so historic accounts and records are often relied upon to assess match ups. Frequently nostalgia has an overwhelming influence on these kind of debates with past fighters taking precedence over modern fighters. For example one might ask; who would win if Harry Greb fought Marvin Hagler? Many would say Greb would easily beat Hagler, but these match ups are inconceivable since footage of Greb's fights are no longer available whilst footage of Hagler's are.

Who would happen if a peak Tyson fought a peak Ali?
This is probably the most common debate in boxing and certainly a very intriguing match up. Thankfully this debate is possible since extensive film of both fighters is available. Before I comment on the fight and who I think would win and why, readers must accept that this prospective fight takes place before Robin Givens, Ruth Roper and Don King came into and out of Tyson's life, a time where Tyson was a very happy and a very proud fighter with an excellent reputation. It also takes place before Muhammad Ali's exile and arguably at the peak of his powers.
Ok here we go...
Muhammad Ali undeniably fought killers all throughout his career and was never intimidated, so to suggest a fight with Tyson would be any different would be anatomically inaccurate. As for Mike Tyson, he is inhibited not by the fighter, but by the moment, so it doesn't matter whether its Jack Johnson, or Joe Louis or Muhammad Ali in front of him, its how Tyson feels on the night that dictates his performance. This should mean that any pre-fight attempt at intimidation or psychological warfare by either fighter would be ineffective and not telling on the outcome of the fight. Therefore this fight is fought and won in the ring. Because of this I Immediately rule out the possibility of a Muhammad Ali win. Why?
Tyson at his peak is simply too skilled and Ali too flawed to beat Tyson. Tyson at his best was a finely tuned destructive machine, splendidly trained with excellent aggressive and defensive skills and he makes very few mistakes. Ali on the other hand has many defensive flaws and makes too many tactical errors in the ring. For example Ali did not know how to properly hold his hands, or how to duck (he pulled back or sidestepped), nor did he know how to parry or block a jab. (The Norton fights are most indicative of this). If you look at Ali on film, he held his right hand out to the side and did not have it in position to block a jab. That is why Ali had problems with certain fighters like Doug Jones and Norton, quick handed fighters with a good left jab and hook have always caused him great difficulty. Ali never learnt the rudiments of classical boxing, he relies on his reflexes and ultra-fast speed for his defense, this became apparent in his later career. Ali holds his hands low, he drops his right hand before throwing a right uppercut from the outside every time he throws it! These defensive pitfalls are perfect for a polished pressure fighting counter pucher like a Mike Tyson or a Joe Louis to exploit.
Ali's best offensive weapon is the left jab and the straight right hand. One of the best things that Tyson does at his peak is to get away from straight punches and to counter with aggression. Ali would be missing all over the place and receiving too many hard fast counter shots in return.
Tyson by KO or UD.