On Monday morning, Charlie pretends to go to school but instead goes to work for Squizzy Taylor. He visits a woman named Dolly, who was present at the boys’ race; Charlie learns that she is Squizzy’s girlfriend. She gives Charlie a new pair of leather boots. Dolly tries to throw out Charlie’s old boots, but he stops her because they belonged to his father. Dolly is sympathetic and immediately puts the old boots in a nice box.
Charlie resists Dolly’s attempt to get rid of Mr. Feehan’s boots because they are his only tangible reminder of his father. His refusal to part with the boots highlights that Charlie is insecure in his ability to grieve; he doesn’t trust himself to properly mourn his father without something tangible to remember him by.
Squizzy comes in, and Charlie confesses that he has come here against Mrs. Feehan’s wishes. When Charlie explains that his mother thinks he is at school, Squizzy arranges for Charlie’s teacher to improve his grades and conceal his absence. Charlie will never have to go to school again, Squizzy tells him, because he is no use to Squizzy with his “[h]ead stuck in a book all day.”
Charlie’s life is changing drastically now that he works for Squizzy Taylor. Squizzy’s readiness to help Charlie manage Mrs. Feehan’s expectations leads Charlie to believe that Squizzy takes care of his employees, which further secures Charlie’s loyalty to him.