Mr. Hundert actually cared deeply about his students, but he was an extremely formal and conventional teacher, and it wasn't in his nature, or his style, to take them aside and discuss personal feelings with them. He was quite repressed about his own emotional feelings, and not comfortable discussing them.
He did get to know his students very well, though. He observed their interests, actions, and activities closely, and he clearly was interested in them. In a restrained way, he got to know them, and they got to know him. He admired Sedgewick and favoured him over the others.He made a mistake in his interpretation of Sedgewick's character, and ever after regretted it. However, he also got to know Deepak, who was avidly interested in classical history for it's own sake, did extra reading outside of class, and Hundert was able to use this insight into Deepak's character to enable Deepak to win the "Mr. Julius Caesar" contest, when it became obvious that Sedgewick was cheating. (Hundert asked an impromptu question about a historical figure who hadn't been mentioned in his classroom, but whom he knew Deepak would likely be familiar with.
He also felt very guilty all his life about bypassing Blythe in favor of Sedgewick, even when as an adult Blythe told him it didn't matter, that he'd more than made up for it. Hundert clearly had a strong influence on all of his students (even Sedgewick) for the rest of their lives.
Hundert was indeed a little bit afraid of interacting with the outside world, which isn't unusual. He was an old-fashioned individual, more academic than administrative. (The school's board of trustees recognized that, which was why they bypassed him for the Headmaster's position, and which clearly came as a shock to him). He also was clearly intimidated during the interview with Sedgewick's father. (But though intimidated, he clearly understood how Sedgewick also was intimidated, and increased his empathy for Sedgewick).
Sedgewick did gain, probably from his father, a realistic view of how the world works. That's why he was so successful as a CEO and politician. He's cynical about truth and integrity. But deep down, he's insecure. He follows the example set for him by his father, but at his father's deathbed, he realizes that he never really knew him.
And it's clear that Hundert was a positive influence on his other students, and succeeded in imparting to them a respect for learning and integrity.
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