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I loved that school. I gave service there to the minds of three generations of boys and always left upon them, if I was successful, the delicate imprint of their culture. . . . That school was my life.

In the beginning of the story, Mr. Hundert defends his time at St. Benedict's as important and significant. He says he left an imprint, suggesting that he was part of the reason why so many of the misbehaving preteens he taught grew up to be notable, powerful adults. Mr. Hundert's tone is persuasive, as if he is trying to argue that his life had purpose and that his presence was as important to the school as St. Benedict's was to him. The school truly was Mr. Hundert's life. He never married or had children. Mr. Hundert only “knows” classroom life. He has little experience outside the walls of educational institutions, so it's important for him to think the time was not wasted.

[B]y then I myself coveted the job of headmaster, . . . but Mr. Woodbridge's death had come suddenly, and I had not yet begun the preparations for my bid. I was, of course, no longer a young man. I suppose, in fact, that I lost my advantage here by underestimating my opponents, who indeed were younger, as Caesar had done with Brutus and Cassius.

When Mr. Woodbridge dies, Mr. Hundert realizes he has not put much thought into how he would lead if he became headmaster despite having been at St. Benedict's for fifty years and coveting the position since Sedgewick was a student. Mr. Hundert describes Mr. Woodbridge’s death as “sudden” even though he was seventy-four years old. What's actually sudden is Mr. Hundert's realization that he can't just step into the role of headmaster without being challenged. Like his teaching career, his goal of being headmaster was a shallow one of surface not substance, rote memorization without application. In setting his eye on the position he’d assumed would naturally become his, Mr. Hundert lacked the foresight that his coworkers might turn on him and try to seize power. This is an especially egregious oversight for Mr. Hundert because it is exactly what happened to Julius Caesar, a series of events Mr. Hundert has been teaching others for most of his life.

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