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

Holmes couldn’t beat Tyson at any point.

 

Some bring up the Douglas - Tyson fight in as a pattern to predict a hypothetical Holmes - Tyson. For the record, I don't consider Larry Holmes and Buster Douglas enough alike to draw conclusions from the Douglas - Tyson fight. I see Holmes as more of a pure boxer, while Douglas, when properly trained, had many Boxer/Puncher tendencies, more so than Holmes. IMHO, of course. I just think that Mike had Larry's number in styles.

 

When they actually fought, notice how nearly every shot landed by Tyson was where Holmes had his back to the ropes or stood stock-still on that first knockdown. Larry, at this stage of his career, just couldn't maintain the movement necessary to get him out of harm's way. This would not be the case with prime Homes which used much lateral movement.

 

At the point he point on boxing gloves for the first time till the time he took them off after fighting Butterbean.