City Boy: The Adventures of Herbie Bookbinder - Plot

Plot

Set in the spring and summer of 1928, City Boy spins the tale of an 11-year-old Jewish boy from the Bronx, New York. The novel first follows Herbert Bookbinder through the final days of school at New York Public School 50, and then through a summer spent at Camp Manitou, a summer camp in the Berkshire Mountains operated by his school's principal. Herbie's city world is one of endless daydreams and small urban pleasures: playing in empty lots, going to the movies on Saturday, arguing with friends around a forbidden campfire, eating "fraps" (sundaes) in Mr. Borowsky's candy store, and going out to dinner at Golden's Restaurant.

Herbie is an exceptionally bright but fat little boy, a seventh grader and a star pupil. Although a poor athlete, Herbie yearns to be a "regular guy" among his schoolboy peers and constantly struggles against the consequences of his own quick wit and natural clumsiness with his rival, Lennie Krieger, the son of the business partner of Herbie's father, Jacob Bookbinder. Both blessed and cursed with a highly-active imagination, Herbie is also on the verge of adolescence, and the story revolves around his continuing quest to win the heart of the fickle, red-haired Lucille Glass.

Herbie, his parents, and his thirteen-year-old sister, Felicia, dwell in an aging Homer Avenue apartment house. Jacob Bookbinder is founder and part owner of an industrial ice-making plant, known to Herbie and his cousin Cliff Block as "The Place," a location that plays both a significant role in Herbie's fate and an adult sub-plot that frames the climax of the story.

Herbie contrives to have himself (and his sister, his cousin Cliff Block, and his rival Lennie) sent to Camp Manitou (run by the principal of P.S. 50, Mr. Gauss, as a source of summer income) when he learns that Lucille Glass will be there. The second half of the novel skewers the summer camp scene of the 1920s even as it sets up a succession of abject failures and spectacular successes for Herbie.

Herbie and Cliff contrive to burglarize "The Place" to finance a well-intended camp project, and that crime is the device by which all the sub-plots come together in Dickensian fashion, at a cost to Herbie's bottom if not his psyche. Wouk fashions a moral to the tale without preaching, but the boy's victory in the quest for Lucille proves tenuous at best.