Mr. Phillips

Mr. Phillips forces Anne to sit beside Gilbert as a theatrical act of discipline after she accidentally brings a bottle of liniment to school, without investigating whether the offence was intentional. The punishment aims to humiliate her, since Gilbert is the boy she holds a fierce grudge against. Ironically, it backfires entirely, reinforcing Anne's stubbornness rather than correcting her behaviour — a small but telling example of his ineffective teaching.

Mr. Phillips writes Anne's name on the blackboard with a mocking inscription, shaming her in front of the entire school. This act serves no genuine pedagogical purpose; it is simply a small man exercising power to protect his own ego. Anne endures the humiliation without being broken by it, and Montgomery uses the moment to highlight both his pettiness and Anne's resilience.

Mr. Phillips is secretly courting Prissy Andrews, an older student in his own classroom, and this romantic interest fuels his professional corruption. He shields Prissy with obvious favouritism, distorting every judgement he makes as a teacher. The students observe this bias clearly, revealing the vulnerability of female students to a male authority figure who blurs the boundary between personal and professional power.

Mr. Phillips leaves Avonlea to study law, a detail Montgomery offers almost as a punchline confirming that he always viewed teaching as a stopgap rather than a vocation. The students feel little to no sadness at his departure, and their indifference serves as a quiet verdict the narrative delivers without editorial comment. His exit clears the way for Miss Stacy's transformative, student-centred teaching.

Mr. Phillips never recognises Anne's intelligence or creativity, treating her as a troublesome oddity and punishing her inconsistently, while Miss Stacy employs fair, curiosity-driven teaching that allows Anne to flourish. The two characters never share a scene, yet Miss Stacy's presence retrospectively condemns every failure of Mr. Phillips's tenure. This contrast is central to the novel's implicit argument about what genuine good teaching requires.

Mr. Phillips is not a villain in any melodramatic sense; he embodies something Montgomery suggests is more mundanely damaging — an indifferent, self-important gatekeeper who holds real power over children's lives while primarily caring about his own comfort and romantic entanglement with Prissy Andrews. He never changes or faces consequences within the story, making him a figure of institutional mediocrity rather than deliberate cruelty.

By seating Anne directly beside Gilbert as a punishment, Mr. Phillips entrenches rather than dissolves their feud, giving Anne's grudge a daily, unavoidable physical form. He acts with no apparent thought for what the arrangement means to either student. The irony Montgomery builds into the episode is that this engineered proximity anticipates one of the novel's most important eventual relationships, all due to his careless disciplinary theatre.

Diana Barry is present as a witness in the classroom scenes where Mr. Phillips metes out unjust punishments to Anne, and her shared indignation reinforces the two girls' solidarity against his authority. As Anne's closest friend, Diana's witnessing of the humiliations validates Anne's sense of injustice. Diana's loyalty ensures the girls' bond is strengthened rather than disrupted by the oppressive classroom environment Mr. Phillips creates.