The narrator identifies himself as a former teacher at St. Benedict’s, an elite private boarding school, and he states that he is writing this story for students of history. The point of the story is to provide a record of his career at St. Benedict’s as well as further information about a “well-known man.” Mr. Hundert then recalls the day thirteen-year-old Sedgewick Bell first entered his classroom. The young boy arrives at the point of the term when the class’s focus shifts from the Greeks to the Romans, so the students are wearing homemade togas. Sedgewick jokes about the boys’ togas, and Mr. Hundert immediately identifies him as a troublemaking distraction. As a result, he doesn’t bother to familiarize Sedgewick with the tablet hanging above the classroom door, something that he typically does with every new student on their first day, which contains a quote from Shutruk-Nahhunte, an ancient king of Elam. Sedgewick quickly becomes popular, leading his classmates in pranks.

After consulting with Sedgewick about his poor grades, Mr. Hundert determines that the only way to make an impression on him is to speak to his father, Senator Bell. Mr. Hundert goes to Washington, D.C., and Senator Bell gives him a firearm purportedly once owned by a servant of Robert E. Lee. Mr. Hundert then expresses his concerns about Sedgewick, and the senator questions what he teaches the students. Mr. Hundert recites a prepared speech arguing that by learning about ancient history, students learn values and morals, as well as what it takes to succeed as a leader. When Mr. Hundert expresses his desire to “mold” Sedgewick’s “character,” the senator plainly tells him that molding his son’s character is his responsibility and that Mr. Hundert’s job is merely to teach him. Humiliated by the senator’s words, Mr. Hundert decides that Sedgewick misbehaves because his father is an unreasonable tyrant. Sedgewick’s classroom performance improves. Because Mr. Hundert’s annual “Mr. Julius Caesar” academic contest only allows the three top-scoring boys to compete, Mr. Hundert decides to inflate Sedgewick’s final quiz score to move him ahead of another student, Martin Blythe, so he can participate with top students Deepak Mehta and Fred Masoudi.

At the start of the contest, Mr. Hundert worries that Sedgewick isn’t ready for the challenge. When he asks Sedgewick his first question, Sedgewick puts his head in his hands and seems to search his brain for the answer, pausing before answering correctly. Mr. Hundert is pleased and continues to ask him easier questions than he asks the other contestants. When it comes down to just Deepak and Sedgewick, however, Mr. Hundert realizes Sedgewick is cheating by looking at notes that he has affixed to the inside of his toga. When Mr. Hundert alerts the headmaster, Mr. Woodbridge tells him to ignore it, or he will lose his job. Mr. Hundert ends the contest by asking a question that is not on the outline but that he knows Deepak will know. Deepak wins the contest, and Mr. Hundert worries he has let Sedgewick down.

After the contest, Mr. Hundert questions whether he did the right thing in not revealing that Sedgewick was cheating. He confronts Sedgewick in his room. Sedgewick doesn’t deny cheating, but he wants to know why Mr. Hundert didn’t expose him during the contest. Even though Mr. Hundert denies it, Sedgewick believes Mr. Hundert didn’t reveal the cheating because his father, Senator Bell, was in the audience. Mr. Hundert stares out the window because he cannot bring himself to meet Sedgewick’s gaze. Frustrated by the meeting, Mr. Hundert continues to wonder if he should turn him in for breaking the honor code but decides against it because of his own crime of inflating Sedgewick’s grade. He seeks out the counsel of his friend and colleague Charles Ellerby, a Latin teacher. Ellerby advises him to contact the senator about the infraction, but before he can, the senator calls Mr. Hundert to confront him for unfairly asking his son a question that was not on the outline. After a stern warning, Senator Bell hangs up on Mr. Hundert, reinforcing Mr. Hundert’s assumption that Sedgewick is afraid of his tyrannical father.

Mr. Hundert relates the later years of Sedgewick’s education, noting that after the contest, Sedgewick’s grades and behavior again declined. At graduation, Mr. Hundert describes Sedgewick as a failure because he wasn’t accepted even to the state university. After graduation, Mr. Hundert loses track of Sedgewick, and the story’s focus shifts to Mr. Hundert’s career at St. Benedict’s and the changing political climate at the school. When a chair position opens, Ellerby competes against an outside applicant who questions the traditions of St. Benedict’s and its focus on the classics. Mr. Hundert stands up to the pressure to bring in new faculty by reciting the same speech he gave in Senator Bell’s office. Charles Ellerby wins the job, and he and Mr. Hundert work together to reinvigorate the study of the classics at St. Benedict’s. Mr. Hundert continues to climb in the ranks of the school’s administration, reaching the position of assistant headmaster.

When Headmaster Woodbridge dies, Mr. Hundert assumes he will receive the position, but Ellerby surprises him by campaigning for the job. Mr. Hundert feels betrayed when Ellerby says his teaching style is outdated. When Ellerby stops by Mr. Hundert’s home and asks Mr. Hundert about the rumor that he keeps a gun in his desk, Mr. Hundert denies the rumor and refuses to open his desk drawer to prove the gun is not there. He feels victorious, and after Ellerby leaves, Mr. Hundert walks in the dark night and throws the gun into the river. He goes to bed certain he will be the next headmaster. The next morning, however, Ellerby becomes headmaster, and he soon requests that Mr. Hundert retire at the end of the term. Before Woodbridge died, Mr. Hundert read a story about Sedgewick Bell’s rise to the chairman position of a successful corporation. As assistant headmaster, he wrote to Sedgewick asking for a donation to the school. Sedgewick responds and asks Mr. Hundert if he will prepare a rematch of the “Mr. Julius Caesar” contest with all of his former classmates in attendance, explaining that he wants to redeem his intellectual honor.

Sedgewick offers not only a donation to the school’s Annual Fund but also to pay Mr. Hundert a stipend. Mr. Hundert takes him up on the offer and begins preparing for the event. Mr. Hundert attends his last graduation at St. Benedict’s and moves off campus to a boarding house nearby. He spends his days walking and visiting the library and museum, and he begins to fear that Sedgewick has forgotten the rematch. Finally, Sedgewick’s office contacts him and arranges for him to fly to a private island owned by his company. On the island, Mr. Hundert marvels at how his students have grown into successful adults, and he feels happy that he contributed somehow to the men they have become. He confesses to Martin Blythe that he should have been on the stage with Deepak and Fred all those years before. Once the competition comes down to just Sedgewick and Deepak, however, Mr. Hundert realizes Sedgewick is cheating again, this time by using a transmitter that looks like a hearing aid, with someone on the other end of it feeding him the answers.

Mr. Hundert again faces the choice of revealing the cheating or keeping quiet. Instead of exposing Sedgewick’s cheating, Mr. Hundert asks a question about Shutruk-Nahhunte, the king quoted on the tablet above his old classroom door. When Sedgewick can’t answer and Deepak wins, Sedgewick congratulates his old classmate and announces that he is running for senator. Mr. Hundert realizes that the point of the event was not for Sedgewick to reclaim his intellectual honor but instead to gather wealthy donors and raise funds for his campaign. After Sedgewick speaks, Mr. Hundert retires to his room and decides to avoid Sedgewick for the rest of the trip. As he waits for his helicopter to leave the island, Mr. Hundert pretends he can’t hear Sedgewick trying to get his attention. Sedgewick comes closer, and Mr. Hundert asks him when he lost his hearing. Sedgewick confesses. Mr. Hundert tells him he hasn’t changed, and Bell tells Mr. Hundert he hasn’t changed either. Mr. Hundert boards the helicopter feeling that he acted honorably by not making a spectacle the night of the competition because he’d had only suspicions without proof. Once home, Mr. Hundert fantasizes about running on stage and pulling out the transmitter during the contest. 

During the first fall term of his retirement, Mr. Hundert follows Bell’s campaign news, reasoning that his interest is normal rather than evidence of an obsession with his former student. When he sees that Sedgewick is speaking nearby at a union event, he decides to attend. During the event, Sedgewick sees Mr. Hundert in the crowd and calls him onstage, thanking his former history teacher for influencing him. Rather than identify St. Benedict’s, though, Bell says that Mr. Hundert was a public-school teacher so he seems more relatable to the miners in the audience. When Mr. Hundert tries to correct him, he realizes his microphone is off. Sedgewick raises Mr. Hundert’s arm, hiding the blazer from view. The picture of the two men appears in several newspapers. Mr. Hundert tells himself he is victorious because he finally spoke out even if no one heard him. The story ends with Deepak visiting Mr. Hundert at the boarding house. Together they watch recently elected Senator Sedgewick Bell in the Senate Judiciary Committee Hearings. As they watch, Mr. Hundert realizes that Deepak has become an old man.