Chris, the toughest and most mature of Gordie’s friends, helps Gordie imagine a different kind of life for himself than the one he seems destined to have in Castle Rock. Chris is a boy with everything stacked against him. Not only is he a target for his violent and alcoholic father and brother, but he is a victim of the town’s judgment of his family. Everyone in Castle Rock believes Chris will simply follow in his family’s footsteps. Even when Chris attempts to defy his reputation by giving back the milk money he steals, Miss Simons denies him that opportunity. Her opportunistic theft of the money suggests that she sees Chris as a lost cause and not worth encouraging to do better. Despite these seemingly insurmountable odds, Chris actively resists becoming like the other men in his family. He refuses to try alcohol. Instead of picking fights or bullying, he is the peacemaker of the group. While his father rages against the very idea of Chris becoming a high achiever, Chris encourages Gordie to nurture his writing talents. He demonstrates that it’s possible to be masculine but still smart and empathetic, inspiring Gordie in his own maturity.

The quest to find Ray Brower is just as transformative for Chris as it is for Gordie. During the encounter with Ace Merrill’s gang, Chris brandishes a gun, asserting his friends’ right to lay claim on the discovery of the body. Ace Merrill’s gang includes Chris’s brother, therefore them claiming the body represents yet another time where Chris is forced to give up what he wants for his stronger, more violent family members. Chris’s entire life is defined by his father and brother because they choose force and violence again and again. Chris’s gun signifies he has a limit, and that he refuses to let this quest be yet another thing his family takes from him. After warning the bullies off, Chris breaks down crying, telling Gordie that he’ll never get out of Castle Rock. His breakdown suggests he believes that brandishing the gun means he has become just as violent as his family. However, the result of this stand-off proves the opposite. After showing that he can stand against men like his father, Chris is able to throw himself into his studies, even willing to face violence and derision to pull himself out of Castle Rock.