On Oct. 2, 1980, former three time heavyweight champ Muhammad Ali came out of a 25-month retirement and fought undefeated heavyweight champion Larry Holmes. During Ali's retirement, he had ballooned up to over 280 pounds. At this time, the 30-year old Holmes was in his absolute prime and had been champ for two and a half years. Ali was two months shy of turning 39, and was an empty package as far as a fighter goes. The only thing Ali had going for him prior to fighting Holmes was his legendary name and mystique. After the second round of the fight, that was gone and Holmes proceeded to beat Ali up for the remainder of the fight (Ali's trainer Angelo Dundee stopped the fight in between the 10th and 11th rounds) in what turned out to be a very sad night in boxing history.
Based on his overall career accomplishments and fighting ability, I would rate Muhammad Ali the best overall heavyweight I've ever seen. Ali no doubt had the most ways and weapons to beat great fighters, more so than any other heavyweight champ in boxing history. It also cannot be disputed that he dominated the best era in heavyweight history, winning the title three times in 14 years.
Despite spending his prime years fighting the United States Government from March of 1967 through October 1970, exiled from boxing, Ali was never defeated in his prime. He defeated three of the top ten greatest heavyweight champions of all-time in Sonny Liston, Joe Frazier and George Foreman. He literally interrupted the title reigns of Liston and Foreman, (who were a combined 75-1 when Ali defeated them) when both were considered unbeatable. It's a well-known fact that when Ali defeated Liston and Foreman, most historians and boxing writers were certain that both of them would reign as champion for years to come. At the time, Liston was compared favorably to Joe Louis, and Foreman was thought to be greater than all the previous heavyweight champs. Had there been no Clay/Ali, Sonny Liston could have been champ through the 60's. Had there been no Ali, George Foreman could've reigned as champ for as long as he wanted; there is no way an undefeated Foreman would have lost to Jimmy Young.
In boxing, nothing sparks emotion and controversy like debating history's greatest fighters and champions, especially when heavyweights are the topic. Using Ali as the measuring stick, fans and historians often debate who would have defeated him or who would've given him the toughest fight. Trying to reach an agreement on this is as difficult as any regarding boxing.
Some of the fighters who are often mentioned who could've defeated Ali are the following: Jim Jeffries, Jack Johnson, Jack Dempsey, Joe Louis, Rocky Marciano and some may mention the names Lennox Lewis, and Mike Tyson. In my opinion, Ali has too many weapons to adapt, and would defeat all of the above mentioned. From a style vantage point, it's obvious that Ali would present those fighters with more problems than they could possibly present him with. Basically, he has defeated other great heavyweights who were similar to the previously mentioned fighters in style and power.
The toughest one of the fighters mentioned is Joe Louis. Ali has never faced a fighter like Joe Louis, just as Louis has never faced a fighter like Muhammad Ali (Billy Conn was not like Ali, the only thing they had in common was their use of lateral movement). Louis was the perfect boxer-puncher. He would have given Ali a tough time because he had fast hands (especially in short and tight spots), a solid defense, carried his punch throughout the fight and wasn't prone to making mistakes. However, I believe Ali's speed and boxing ability from outside, overall strength and cast-iron chin would have carried him past Louis. Style wise, Ali has the advantage, because Louis pursued but not as aggressively as Marciano or Frazier. Louis focused on drawing his opponents to come to him so he could nail them on the way in, Ali would have never fallen into this trap and would have been able to dictate the pace and fighting distance vs. Louis. The immortal “Brown Bomber” was also vulnerable when he had to move his feet quickly to chase an opponent who wasn't hurt, which also is to Ali's advantage. Although I'm confident Ali would have defeated Louis, it would have been a close fight and not a walkover as some have suggested.
The fighter who I believe would have given Ali the most trouble strategically and stylistically is former heavyweight champion Larry Holmes. Some of the above mentioned fighters would have given Ali a rougher fight from a physical vantage point than Holmes (like Jeffries, Dempsey, Marciano, and Tyson). However, from a style match up, none of them could have answered and matched Ali technically like Holmes could have. I can't see any other heavyweight outside of Holmes who had the skill and style to possibly upset Ali at his best. A lot of what Holmes did in the ring were things Ali didn't face too often.
When comparing Ali and Holmes, they are mirror images of each other in many ways. They are virtually the same height and have the same reach. I think the differences were, Ali was a little stronger and faster, had a better chin and possessed better stamina and legs when he was in top shape. Ali was also better at adapting during the course of a fight than Holmes was. That being said, none of those advantages, other than Ali's speed, would've come into play had Ali and Holmes crossed paths at their best.
Had Ali and Holmes fought in their respective primes, I think it would have been a dull fight because of their many similarities. A big reason Holmes would have been effective versus Ali is that he wouldn't have been trying to kill him with every punch he threw. The fighters who tried to kill Ali are the ones he ate up. Holmes fought at a more measured pace, somewhat like Ali. Fighters who didn't try to knock Ali out with every punch were more troublesome to him. The fighters who tried to take him out, he killed with his speed by taking advantage of their mistakes and countering them off a miss.
Both Ali and Holmes had great jabs, and used them perfectly to set up their offense. The difference was, Ali's was faster and he threw more, but Holmes' was a little harder. What makes Holmes a problem for Ali is that he hated to be jabbed at. Fighters who jabbed back at Ali gave him the most difficulty; look at his fights versus Doug Jones, Jimmy Ellis, Jimmy Young and Ken Norton. As great as Ali's jab was, fighters who jabbed back sometimes befuddled him. Also, not many fighters attempted to jab with Ali. Therefore, he wasn't used to jabs coming at him. None of the fighters mentioned had a jab in the same class as Holmes, and we know Holmes would be jabbing back at Ali. Although Holmes didn't like to be jabbed at, it didn't bother him as much as it did Ali. Holmes was bothered more by pressure, as was Ali, but not as much as Holmes. Another problem Holmes presents Ali with is that his hands were very fast, not as fast as Ali's, but faster than any Ali opponent except for Floyd Patterson, except, unlike Patterson, Holmes had a reach equal to Ali's.
Another given in this fight is that it would have gone the distance. Both fighters had great chins and neither had the one-punch power to stop the other. In my opinion, Holmes had the skill to match up quite well with Ali. Yes, I think Ali would have won a decision over Holmes due to his speed and overall better adaptability, but this would have been a very taxing fight for Ali, mentally and technically. In my opinion, Holmes wouldn't do as well with a prime Frazier or Foreman as Ali did, however he would have been pure hell for Ali! I believe Larry Holmes most likely would have been the toughest heavyweight champ in boxing history for Ali to look good against and achieve a decisive victory over.
One factor in Ali's favor in a match up with Holmes is that Ali would have lured Holmes to pursue him. Both fighters liked their opponent coming to them; neither Ali or Holmes were at their best when they had to play the Joe Frazier and seek and chase down their opponent (see Ali vs. Young and Holmes vs. M. Spinks). The fighter who is the one pursuing in this fight is at the disadvantage strategically. I believe this is the one style match up that favors Ali in a big way. Had they fought in their primes, I see Holmes going after Ali much more than I can envision Ali pursuing Holmes. In this scenario, I see Ali's speed advantage playing a major role. Again, most likely Ali wins. However, I see Holmes a very difficult night for him from the first to last bell.