While some of the other caddies at the Sherry Island Golf Club are poor, Dexter Green’s father owns the second-best grocery store in Black Bear, MN. Dexter, therefore, caddies every summer for the wealthy patrons of the Sherry Island Golf Club not because his family needs the income, but rather because Dexter wants pocket money. In the winters, he skis over the desolate course and spends the remaining seasons fantasizing about returning to the course one day as a glamourous, wealthy patron.
Dexter is introduced as someone concerned with rank and status. His father’s business is the only mention of his family background, suggesting that Dexter’s familial connection is defined by how it positions him socially. The desolation he feels during winter is relieved by his fantasy of upward social mobility.
Dexter fantasizes about defeating T.A. Hedrick (an elite member of the golf club) in a golf game and becoming a champion. He also imagines himself stepping from “a Pierce-Arrow automobile, like Mr. Mortimer Jones,” another wealthy club member, and “[strolling] frigidly into the lounge of the Sherry Island Golf Club.”
One day, Dexter meets Mr. Jones who, “with tears in his eyes,” tells him that he is sorry to hear that Dexter will no longer be caddying at the club. Dexter claims to Mr. Jones that his decision is based on his being too old to caddy, but in fact his decision is based on an interaction that he had with Judy Jones, Mr. Jones’s daughter, earlier that morning.
Dexter does not want to upset Mr. Jones by mentioning the true cause of his decision. However, his excuse of being “too old” is partially right, for he thinks that he is too old to take orders from Judy.
Eleven-year-old Judy Jones had arrived on the course with her nurse, Hilda, at 9:00 AM. Though she comes with “a white linen nurse” and “five small new golf-clubs in a white canvas bag,” Dexter notices that she appears “ill at ease.”
Judy has learned how to maintain the appearance of her social class. She travels with a servant and carries white objects, a color associated with the wealthy leisure class.
Judy calls to Dexter to inquire about the whereabouts of the golf teacher and the caddy-master, neither of whom are present. Hilda reveals that Judy’s mother sent them out to play golf, but that they do not know how without a caddy. This indiscretion upsets Judy who gives her nurse “an ominous glance.” While walking away from Dexter, Judy attempts to hit Hilda with a golf club, a sight that amuses Dexter.
Judy is angry with her nurse for revealing to Dexter, someone of a lower social class, that she does not know how to play golf. Judy’s abusiveness foreshadows her haughty behavior toward Dexter. However, because she directs her abuse toward someone beneath Dexter’s class, he is amused rather than affronted.
When the caddy-master appears, Hilda tells him that Dexter was unable to take them out on the course because he had to await the caddy-master’s arrival. The caddy-master’s return prompts Judy to drop her clubs for Dexter to pick up, since she assumes that Dexter can now help her. The caddy-master agrees that Dexter is free to help them, but Dexter refuses to caddy for them and simultaneously quits his job. He worries about losing the money—thirty dollars per week, which could not be made elsewhere around Black Bear Lake. However, in this instance, as in so many others, he was “dictated to by his winter dreams.”
Dexter’s pride, influenced by his dream of social prestige, prevents him from taking orders from Judy. She is younger than he and female, which makes him feel that it would be inappropriate to take orders from her, though he would take them from her father. However, his pride comes into conflict with his desire to make money and to achieve economic success. In the end, he decides that he cannot achieve social prestige without maintaining social principles.