In "Winter Dreams," Dexter's fantasies relate to his acceptance by established members of the Sherry Island golf club.
Dexter was not poor. However, it is very clear that as a caddy, he is not part of the socially accepted elite that populate the Sherry Island golf club. He might caddy "only for pocket money," but he finds the world of the Sherry Island Golf Club extremely appealing. It helps to fuel his "winter dreams" that "command imaginary audiences and armies."
One of Dexter's fantasies involves his his talent at golf. He defeats "Mr. T.A. Hedrick in a marvelous match played a hundred times over the fairways of his imagination." This fantasy sometimes unfolds with defeating Hedrick in a dominant manner or coming from far behind to best him. Another fantasy involves his swimming abilities. He fantasizes about how he would astonish members with his swimming abilities by giving "an exhibition of fancy diving from the spring- board of the club raft." As he astonishes the crowd, Dexter imagines that club members like Mr. Mortimer Jones would watch him in "open-mouthed wonder."
In Dexter's fantasies, his impressive presence at the Sherry Island golf club enables others to view him with wonder and awe. Dexter's fantasies move him from being an "outsider" to a part of the established and elite members of the Sherry Island golf club.