(Comprehensive Guide to Short Stories, Critical Edition)

Basil T. Lee, the fifteen-year-old protagonist of “The Freshest Boy,” is first introduced to the reader as the swashbuckling hero in the scenario of his escape into fantasy from the lonely, hostile reality of the prestigious St. Regis school for very rich boys. This scene is contrasted with an account of Basil’s train ride from the Midwest to St. Regis and his anticipation of what his life at the school will be like. He has been so steeped in the tradition of attending an Eastern boys’ school that “he had a glad feeling of recognition and familiarity. Indeed, it was with some sense of doing the appropriate thing, having the traditional rough-house, that he had thrown Lewis’s comb off the train at Milwaukee last night for no reason at all.” On this trip, Lewis, a fellow student from the Midwest, reminds Basil that his reputation at his former school was that of being “a little fresh,” and Basil resolves to make a new start, fantasizing about being a football hero.

At school, Basil is embarrassed that he is not from a wealthy family and writes his mother, stating, “All the boys have a bigger allowance than me.” Basil feels humiliated when Dr. Bacon, the headmaster, confronts him with his poor grades and emphasizes the Lees’ financial sacrifice in sending him to St. Regis. These humiliations are made more difficult to bear by the fact that Basil is aware that he is the least popular boy in school. Within the first few weeks he has gained the nickname of “Bossy” and has been involved in several fights. Consequently, it is November before the headmaster agrees to let Basil go into New York City for the weekend, and then only on the condition that he find two other boys to accompany him, which proves an impossible task. Basil sneaks off the grounds to find the only three boys who might even consider going with him. He finds Bugs Brown, who is so strange that he can associate only with “boys younger than himself, who were without the prejudices of their elders.” An appointment with his psychiatrist prevents Bugs from accepting. Fat Gaspar, a generally amiable boy, gives in to peer pressure, and rather than tell Basil that he cannot go to New York City, he laughs at him and tells him that he does not...

(The entire section is 913 words.)