Dexter's first meetings with Judy Jones are the impetus for his "Winter Dreams." A lowly caddy, Dexter meets the haughty little girl, all of eleven years old, on the golf course. Her derision of him makes him rethink his life. When Judy bangs up her clubs in a fit of temper, the caddy-master demands, "What are you standing there like a dummy for? Go pick up the young lady's clubs."
Instead of suffering her insults, Dexter impetuously declares:
"I think I'll quit.
The enormity of the decision frightened him. He was a favorite caddy and what he earned through the summer was not to be made elsewhere in Dillard. But he had received a strong emotional shock and his perturbation required an violent and immediate outlet.
Dexter works hard to prove to Judy Jones that he is one of the elite, if not by birth, and her equal. By the end of the story though, Dexter realizes how hollow, like a dry twig in winter, that his lifelong dream, has been.