Excellent list.
I have been probing to see where there might be an opening. This man is a college “communications” professor. He is a high school friend who was on the debate team with me. Used to be level headed as a teen, but lost it along the way.
Start with Allan Bloom’s “Closing of the American Mind.”
When I was pursuing my Master’s in English Lit. (unfinished) it opened doors with many people, even hard-left professors, when I used it to counter their leftist views.
Hopefully, since your friend is in education, he would show an interest in the decline of academe. Of course, he may have already read it and immunized himself to its argument.