Yes, I got a very strange vibe reading that Simon paper, as funny as parts of it (like the concluding advice on how to make good use of your friends) were, and as seminal a figure as he has been in AI and related fields.

After thinking about it, I think the issue is that Simon is coming from the Good Old Fashioned AI point of view of messing around with random Lisp code without any kind of principled background such as statistical models, and this leads to a kind of subtle semantic drift on all sorts of points and vocabulary - a kind of Uncanny Valley effect. Just similar enough to disturb one.