|The stupid question is the question not asked|
Agreed, but there is a difference.
As given, ie. without context, either interpretation of either phrase is equally valid. And that is for a human being!
The problem then is not how to make a program that can disambiguate the possible interpretations. It's simply one of: How to disambiguate the possible interpretations. Not so much an AI problem as an HI problem.
If we had some context, like an earlier reference to "the man with the telescope", or "John was using his telescope", then human beings easily make the correct interpretation. Programming that is hard, but far from impossible. Given enough examples of it, a NN could probably make pretty good guesses much of the time.
As originally stated though, without context, the problem is impossible, but it is equally impossible for the human as it is the computer.
Examine what is said, not who speaks."Efficiency is intelligent laziness." -David Dunham
"Think for yourself!" - Abigail