Holling demonstrates growth through defeat primarily in his relationship with Mrs. Baker. Initially feeling oppressed by spending Wednesday afternoons with her instead of engaging in religious studies, Holling sees this time as a "war" he is losing. However, as Mrs. Baker introduces him to Shakespeare, Holling's perspective shifts. He learns to appreciate and understand Shakespeare, which helps him grow personally, improving his relationships and self-awareness.

Holling wins the cross country race through a combination of natural talent, hard work, determination, and the expert coaching of Mrs. Baker, a former Olympic medalist. His awareness of potential saboteurs helps him stay focused and prepared. The victory is significant as it boosts Holling's self-esteem, deepens his respect for Mrs. Baker, and strengthens his bonds with friends, offering him positive reinforcement amid a difficult home life.

Mrs. Bigio begins to be nice to Mai Thi after witnessing her being bullied at school, which makes her realize her own bullying behavior towards Mai Thi. Initially, Mrs. Bigio's attitude was influenced by her grief over her husband's death in Vietnam, leading to misplaced anger towards Mai Thi. Recognizing her actions, Mrs. Bigio apologizes and starts to make amends by preparing Vietnamese food for Mai Thi, signaling a change in her attitude.

Mrs. Baker means that experiencing defeat can lead to personal growth. She illustrates this by discussing the Apollo missions' perseverance despite setbacks and implies that Holling will learn this lesson throughout his year. She suggests that defeat is not the end but an opportunity to improve and move forward, challenging Holling's initial belief that defeat only brings negativity.

In "The Wednesday Wars," Holling Hoodhood's character development is shaped by various events and relationships. Initially a fearful child, Holling matures through experiences such as his interactions with Mrs. Baker, learning empathy and selflessness. Key events include rescuing his sister, confronting his idol Mickey Mantle's flaws, and gaining insights from Shakespeare's plays. His friendships, especially with Meryl Lee and Danny Hupfer, teach him loyalty and courage. Holling also grows by understanding war's impact and overcoming discrimination, ultimately standing up to his father's expectations.

In The Wednesday Wars by Gary Schmidt, Holling Hoodhood learns significant life lessons through his experiences and interactions, especially by studying Shakespeare. He discovers the complexity of human nature, understanding that people are often shaped by societal expectations, as seen in his reflections on Shylock from The Merchant of Venice. Holling learns to empathize with his father, viewing him less as a villain. His growth is also reflected in his relationships, particularly with Mrs. Baker and his sister Heather, where he learns about loyalty, trust, and standing up for one's beliefs.