Benedict Arnold plays a prominent role in the story, as Truly wants to put on a play about Arnold for the History Day project. Arnold’s story builds a connection between Truly’s eighth-grade experience and political warfare. Truly writes the play herself, and she doesn’t give herself a role, alluding to her outsider status. Lulu plays John Andre, a French-born English intelligence officer who led the negotiations to acquire West Point. Evangeline plays Arnold. Lulu’s and Evangeline’s roles don’t have overt connections to their roles at school. However, Brooke plays George Washington, as she’s the most popular girl in school. Natasha plays Peggy Shippen, Arnold’s second wife.

Shippen came from a wealthy family of loyalists who wanted America to remain under British rule. The article “Why Did Benedict Arnold Betray America?” provides a summation of Arnold’s motives for betraying America, which relate to Shippen: The English offered Arnold £10,000 to access West Point, and Arnold could give Shippen the affluent life she was accustomed to (Seven, John. “Why Did Benedict Arnold Betray America?” History. 20 Sep. 2023). Thus, Lulu quips, “So wait. This Peggy girl? She totally played Benedict, right?” (356). The novel links Shippen’s scheming to Natasha’s plotting, indicating that Shippen compelled Arnold to become a traitor.