How does "Winter Dreams" influence our understanding of The Great Gatsby?

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There are significant thematic similarities in The Great Gatsby and the short story that preceded it, "Winter Dreams." Both Dexter Green and Jimmy Gatz aspire to rise in society to gain access to a world heretofore out of their reach. Dexter has perhaps a better understanding of the world to which he aspires, because he has caddied for years at the golf club where affluent men and women socialize. Jimmy Gatz, on the other hand, has a much more restricted view of the wealthy, having only seen the isolated world of Dan Cody on his yacht. Jimmy Gatz's origin story reflects roots that are more humble than Dexter's, making his financial success all the more dramatic and life-altering and at the same time making him less prepared to navigate the milieu he seeks to join.

In both the story and the novel, a woman figures prominently, and both are similarly flawed. Judy Jones and Daisy Fay are both rich and spoiled and quite cavalier in their dismissal of others' feelings. Dexter seems to have a clearer understanding of Judy's faults than the man who reinvents himself as Jay Gatsby has of Daisy's foibles.

In following "Winter Dreams" with The Great Gatsby, Fitzgerald deepens his exploration of social mobility, escalating it from illusory and empty to illusory and ruinous.

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Writing “Winter Dreams” in 1922, Fitzgerald created characters and developed conflicts and themes that made their way into The Great Gatsby where they are more fully realized and artistically rendered. Dexter Green is not Jimmy Gatz or Jay Gatsby and Judy Jones is not Daisy Fay Buchanan, but the parallels between the story’s characters and those of the novel are numerous; moreover, it is in the similarities that the heart of The Great Gatsby is found. Dexter’s pursuit of his dreams and his romantic idealization of a shallow, selfish young woman clearly foreshadow Gatsby’s. The destruction of Dexter’s romantic illusions and the death of his dream are forerunners to the major themes in the novel.

The basic details of Jimmy Gatz’s personal history originate in Dexter Green’s. Dexter is born into circumstances he longs to escape. As a boy, he is restless, ambitious, and subject to romantic fantasies; he wants “glittering things” and “[reaches] out for the best ….” He creates a new life and a new image for himself, builds a fortune, and lies about where he had grown up.

Much of Dexter’s relationship with Judy Jones is reflected in Jay Gatsby’s love affair with Daisy Fay in Louisville before they are separated by World War I. The daughters of wealthy men who own large, impressive homes, Judy and Daisy are both beautiful, charming, and irresistible to the many young men who vie for their attention. Dexter’s obsessive love for Judy prefigures Gatsby’s obsession with reliving the past with Daisy. Like Dexter, who idealizes Judy and lives with the illusion that she is worth having, Gatsby idealizes Daisy and finds it impossible to confront the reality of who and what she is. Years after falling in love, both Dexter and Gatsby are nourished by their romantic memories and think of Judy and Daisy, respectively, as they once had been.

In the conclusion of “Winter Dreams,” Dexter’s cherished perception of Judy is destroyed, and he suffers the loss of an essential part of himself—the ability to live through his memories in “the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.” Dexter’s pain as he realizes what “had been taken from him” is the pain Gatsby desperately attempts to escape by denying reality and dedicating himself to his dream of Daisy and all that it embodies. Whether Gatsby is still living in the “country of illusion” as he waits for Daisy’s phone call in the novel's conclusion—or if his dream dies before he does—is subject to conjecture. In this respect, the romanticism of Dexter Green is intensified in Gatsby, and Dexter’s sadness is elevated to tragedy with Gatsby’s murder.

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