Jack Crabtree is the brother of Miss Crabtree. He seems to possibly be a traveling salesman, passing through Greenpoint to visit his sister and good-naturedly tease her for becoming a teacher. When he tries to catch up with her at school, he runs into what he suspects might be a bad situation. Her students aren't receptive to strange men who might court their favorite teacher away from them. Mary Ann isn't friendly to him and nearly bites him. The boys dispel far-fetched rumors to scare him off from courting their teacher. Jackie Cooper tells him that Miss Crabtree powders her face, puts red stuff on her lips and has two sets of false teeth and a wooden leg. Farina Hoskins remarks she has a tendency to "chunk up." Buddy MacDonald reveals she has seven husbands to which Speck Haines adds twenty-one kids. Jack just chuckles away their claims and wanders off to go swimming, but the boys steal his clothes to keep him from returning. This predicament leaves Jack only the recourse of borrowing a dress from a lady to get back to the schoolhouse where Wheezer, Stymie and Echo have already found his clothes.
Jack Crabtree was played by Creighton Hale.