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In "Winter Dreams," what summer fantasies does Dexter indulge in at the Sherry Island golf club?

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In "Winter Dreams," Dexter's fantasies about summer at the Sherry Island Golf Club reveal his desire to be a member of the wealthy, prestigious Black Bear community. The fantasy of arriving at the club in Mortimer Jones' Pierce-Arrow automobile is particularly telling, because it reveals Dexter's desire to identify with and emulate a member he perceives as belonging.

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In another fantasy of being a patron at the Sherry Island Golf Club where he caddies, Dexter imagines himself stepping from "a Pierce-Arrow automobile, like Mr. Mortimer Jones," and "[strolling] frigidly into the lounge of the Sherry Island Golf Club." Though it is never stated directly, it seems that Jones is the wealthiest and most prestigious member of the club and the community of Black Bear, Minnesota. Jones is mentioned in tandem with Dexter's fascination with and desire for the material wealth that he eventually attains. Also, Jones is the father of Judy Jones, with whom Dexter falls in love.

Judy is admired by Dexter not only for her beauty but also for her social status. He loves Judy for what she represents to him; marrying her would make him a member of the wealthy community to which he hopes to belong. When he imagines "[strolling] frigidly" into the club,...

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it is with a stiffness that comes from the unshakable confidence and security that comes from belonging. He imagines himself as Mortimer Jones because Jones is the person on the course whom Dexter most wishes to be like.

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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.

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