The following version of this book was used to create the guide: Perrotta, Tom. Tracy Flick Can't Win. Simon & Schuster, Inc., 2022.

Tom Perrotta's novel Tracy Flick Can't Win is narrated from the first and the third person points of view. Chapters marked with the characters' names indicate whose first person point of view the chapter will present. Chapters that are not marked with a character's name are written from the third person limited point of view. The text takes creative liberties with form and structure throughout. The following summary, however, embraces a streamlined and linear mode of explanation.

When Tracy Flick learned that her boss Principal Jack Weede would be retiring at the end of the year, she was filled with hope. Although Tracy enjoyed her job as Green Meadow High School's Assistant Principal, she longed for more authority and respect. Her life in Green Meadow, New Jersey had not amounted to the life she once dreamed of. After graduating from high school, Tracy moved away from home and her mother to pursue a career in politics. When she later learned that her mother was dying of MS, she moved home to take care of her. She had to drop out of law school and abandon her political pursuits. When she started substitute teaching, she felt a renewed sense of purpose. This part time work eventually evolved into a career in education.

Prior to Tracy's work in the Green Meadow High School community, she attended graduate school. During this time, she had an affair with one of her professors, a man named Daniel. Tracy would have faded into Daniel's past and Daniel into Tracy's, if Tracy had not gotten pregnant. She planned to have an abortion because she was still in school and had little money. At the behest of her dying mother, however, she decided to go through with the pregnancy, even involving Daniel. Daniel surprised Tracy, insisting that he wanted to be a part of the baby's life. Tracy and Daniel now had joint custody of their daughter Sophie.

At the start of the new school year, the newly elected President of the School Board Kyle Dorfman called a meeting with Tracy. He assured Tracy that the Principal position was hers. He then asked for her help establishing a Hall of Fame at GMHS. Although Tracy did not support the project, she agreed to help, desperate for Kyle's backing.

Over the course of the following months, the Hall of Fame Selection Committee, including Tracy, Kyle, Jack, and students Lily Chu and Nate Cleary, sifted through nominee profiles. Eventually they decided to induct former graduates Vito Falcone and Diane Blankenship. Vito Falcone was an ex football star. Diane Blankenship was the longtime front desk secretary.

As the Committee planned for the upcoming Hall of Fame Induction Ceremony, tensions rose in Tracy's personal and vocational spheres. She broke up with her boyfriend. Memories of her past kept returning. She discovered that the Board planned on hiring the former football coach as Principal instead of her. The more conflicts that accrued around her, the less capable Tracy became of remaining calm and centered.

On the night of the Induction Ceremony, Tracy tried to privately make plans for her future beyond Green Meadow High School. Lost in thought, she failed to notice a strange man diving towards the stage with a gun. The man was Glenn Keeler, a former GMHS student who had a grudge against inductee Vito. He shot and killed Vito and injured Tracy.

In the year following the shooting, the community attempted to heal. Tracy was appointed Principal and inducted into the Hall of Fame. She finally realized how vital she was to her community.