Like a bunch of observers giving an account to the police of a road accident - we all see this from a different perspective - we have all had enough differences in our lives and our experiences with teachers as well as, various classmates, some who go on to live fuller lives than others.
And so I would be shocked if we came down to one viewpoint about any of these characters, what the story has accomplished or even to agree on what is a thought versus a feeling.
E.g. to me when Mr. H. says he hopes does not suggest a feeling of yearning that the word hope can convey - to me it sounds like - If I, Mr. H. had my druthers... - which is giving a nod to, if I could control the event, another, the outcome, whatever...
The same to 'know a look' - which is saying I have a gut reaction based on my past experiences - reminds me of the game popular in the early 70s of showing photos of folks and we guessed based on appearance and facial arrangement what was going on with the person. All it did was prove to us we make judgments about others by sight based on our own experience or interpretation. Plus the verb is to know - regardless if he felt warm towards, leery of, delighted with, suspicious of, Mr. H. 'knew' the look which altered his opinion of what he was looking at based on his own history.
My take is we would not have a story that was without opinion as if a non-biased report - we have a character telling a story that is based on the backstory of this character - the story is told by him. His version of what happened that would come out of what he understood was his job and how he performed that job given his assessment of the behavior of others and like all of us, through the screen of our past experiences, cultural association, education, social skills, emotional balance and sophistication.
I think back to Dana's comment about the arrogance of anyone thinking they should mold another - regardless 'molding' seems to still be a feature of some schools its really today not even seen as a job for a parent - parent classes for over 20 years are about how to guide, offer opportunity, decision making together etc. Where as when mold was the way, that meant, do all you can to make someone believe and behave a certain way - with the word 'make' being the operative word.
We make things - we influence people - many of us were educated during the 'make students into' time in education and is why we have memories of punishment or coercion - the 'power over' model - I will make you, hone you, pound in a level of competence, sweetly introduce that you are expected to enjoy or at least learn from etc. with no concern for a student's personal learning style or life experiences. The narcissistic "when you are in MY classroom you will..." was rampant.
Today we know differently and realize teaching and learning is a team effort that starts with the two year old when, rather than 'make' them do something they are given two choices e.g. it is time for you nap do you want to take such and such stuffed animal or the quilt grandma made - do you want milk when you wake up or grape juice and so a classroom continues to be a place where the experience of students outside the classroom becomes part of the group learning references.
Compared to teachers from the 'make' or 'mold' school of thought this link I think is a good one that lists the attitude and work of a teacher today.
http://www.edutopia.org/discussion/heart-teaching-what-it-means-be-great-teacherWe know that Mr. H. had good intentions and was a good teacher using a different older standard to measure a good teacher - and yes, it is a stretch for us to place ourselves in those classroom years and for others of us it was an easy recognition but regardless, we were hearing about the experience of Mr. Hundert and how he taught with the mindset of a 'make' or 'mold' directive in his job - he was not successful regardless the reasons; regardless the support or lack of, regardless the different expectations of the others in the story - his directive was to mold his students to live with a certain value system and he did not do it with at least this one student. And we see evidence that he did not always live up to his own values regardless the because.
And so he was reminiscing on his career efforts - when anyone has a failure we are not comfortable believing it was all our fault and part of our storytelling is to make sure we see the fault in the other or the system that allowed you, with the best of intentions, to fail. He does a fairly adequate job of admitting his own mistakes but, he does not go deep into unraveling his expectations for certain intimacies or how he projected expectation for the behavior of others, based on protocol, tradition, shyness, his own limited view on relationships in or out of the classroom.
In their old age he does not develop a more intimate friendship with Deepak than he did with Sedgewick or Hyram those many years ago - we only have his thoughts on the friendship he developed with Charles Ellerby so that we really do not know, more than a few personal opinions, how strong and informal was the friendship - if it was anything like the friendship he maintained with Deepak, who was probably only about 10 years younger, then, the friendship with Charles may not have been any more intimate and his expectation for loyalty may not have been realistic or at minimum based on a code of honor that was a leftover from the days when relationships were a surface encounter.
Bottom line, I see this story as a tell all - a sorta confession that also suggests Mr. Hundert's good opinion of himself and how he performed his job that included a failing attempt to mold the character of student who became a public figure as well as, pointing fingers as part of the cause of this failure.