Is the subject of the question (he) “That man” or “That man’s father”

In english language this is called an ambiguous antecedent. The pronoun “he” could refer to “That man” or “That man’s father”

Now if you say “I am looking at a picture of someone and that man’s father is…” then the it might seem logical that the subject of my question is the person I am looking at in the picture, which would clearly(?) imply the subject of my question (he) is “that man”

But in another context, I am in a crowed room, and I am talking to a friend. I point to a person across the room and say “that man’s father used to be [on TV/the mayor of Schenectady/date my wife]. Who is he?”, my friend might infer that i am seeking the identity of the “that man’s father” and not the man I am pointing to, and therefore the subject of my question (he) is “that man’s father”

Of course, in either case the opposite could be true, and hence the ambiguity.

which makes this the perfect riddle/bar bet**… because after the has concluded their logic, you can simply switch your context and say no, “he” refers to [the opposite of what was answered].

** it is only the perfect bar bet if you are big or can run very fast.

@Andy You’re incorrect on the first example. It simplifies to “that man’s father is me”, and you cannot be your own father. (Your father’s son is you if you have no siblings).

@Jackson earle My father’s son is indeed himself, but he says this man’s father is himself.