At what point in his career could Larry Holmes no longer defeat Mike Tyson?

All of it. Terrible match up for him.

 

IMHO, this. ^

 

The Holmes from 1978-82 could beat Mike Tyson

 

The Holmes of the Cobb fight would have stopped Mike in 8. A bit past that, Mike beats him.

Not at all, Buster Douglas on his best day wasn't prime Larry Holmes. Convince me otherwise.

 

I think a properly prepared (physically and mentally) prime Mike Tyson would normally beat a properly prepared (physically and mentally) prime Larry Holmes most times. They were both elite heavyweights and the styles favor Mike.

 

This. Even in 1988 when Holmes was old and inactive was frustrating Tyson just with his experience, so Larry when he was younger and still had lightning fast counters would definitely have a good chance of beating Tyson.

 

I will make no comment on how it goes prime for prime.

Given Tyson's short prime, and Holmes's incredible longevity, there is almost certainly some sweet spot where Holmes wins.

Frankly, you could possibly have found such a place, in the actual timeline.

 

The way I see it, the Tyson that lost to Douglas was a prime Tyson, or damn near, so if Buster could overcome and prevail over Mike, for my money so could a peak Holmes, Douglas showed the way, mapped out the blueprint for winning against Tyson, of course it goes with out saying you would need a very good chin, be full of confidence, and able to box and move, and have good stamina , remind you of anyone ? stay safe guys.

 

If I were to construct a hypothetical fighter in terms of skill, physical attributes and moxie as the perfect remedy to Tyson, the prime Holmes that actually WAS would be among my top design choices.

I guess we can say that as at 1988, when they did actually fight, Larry could no longer beat Tyson.

However, even then, Holmes wasn’t at his post prime, full potential - apologies since I understand that such considerations are only reserved for Mike - no one else, of course.

 

You mean like Buster Douglas being a terrible match up for Mike?

 

If Larry Holmes could of had a few tune up fights to get his rhythm back he would of game Tyson worlds of trouble. Larry was out of the ring for what 2 years? Even when a younger Tyson Fury took 2 years off he didn't come back with a tough fight.

 

More often than not Tyson beats Holmes.

 

I think Holmes would beat post prison Tyson and Tokyo Tyson, and would be close to even odds against the Tyson from Williams, Bruno, and Ruddock. Tyson would have a chance even in poor form due to sneaky power.