How many matches would Holmes win?

Vs. Louis? 2
Vs. Lewis? 2
Vs. Ali? 1

5-4 or 6-3

 

Holmes 1978-1981 vs.
Louis 1937-1940
Ali 1964-1967
Lewis 1997-2001
Holmes is my #6 all time heavyweight
Louis is #1, Ali is #2 and Lewis is #4.
If this was a one time prime for prime match up I'd pick them all to beat Holmes. However I think it is reasonable to expect Holmes to win one out of three against them. He's every bit a good of a boxer as any of them. With the exception of Lewis he's not at any real size disadvantage. Holmes bigges weakness is his ego.

vs. Louis: Holmes world famous jab is going to have to be on point. If I were a trainer of someone facing Joe Louis my game plan would be to stay on the outside and box. The best example is how Walcott fought Louis. I should point out that that was in 1947 and 1948 and that Louis won the first by split decision over 15 and a KO in the 11th. My point is that there is no "blue print" to beat Louis. I'm not sure Holmes has the power to hold Louis off of him. If Holmes can hold off Louis for 12 or 15 rounds he might get a decision. If not I see Louis getting a decision or win by stoppage.

vs. Al: If I had to put money on this bout I'd put it on the over.
Rather this goes 12 or 15 rounds I think we are going to see a decision. This is going to be a "boxing match" rather than a "fight". Neither Ali with a 60.66 ko % or Holmes with a KO% of 58.67, are great punchers for heavyweights. Both have pretty solid chins.
I think the key for Holmes is to stick to fundamental boxing and not try to impersonate Ali. I think that is going to be an interesting match up. Not in the sense that it is going to be an exciting fightbut in the sense that it is going to be a closely scored contest.

vs. Lewis. Lewis's two losses are by knockout. I don't see Holmes stopping Lewis. This is the match up due to Lewis's style and size that Holmes is most likely to go 0-3. Holmes is a better boxer than McCall and Rahman, but they are better punchers than Holmes. Lewis's jab may not be as good as Holmes but he has a very effect jab in his own right. Considering that Lewis has a 3" reach advantage and that he's more than willing to stay on the outside all fight. I see Holmes eating Lewis's jab all night. If Holmes decides to go on the offensive he's going to walk into Lewis right hand. Honestly I don't see Holmes winning here.