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

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.

What themes and characters do "Winter Dreams" and The Great Gatsby share?

In some of the literature on Fitzgerald, "Winter Dreams" is cited as a "draft" of what became Gatsby. The parallels between Dexter and Gatsby and those between Judy and Daisy are certainly present. Some of the color motifs are shared, although they are fairly consistent in much of Fitzgerald's work. White, silver, and gold are associated with wealth and the privileged class. There are many references to all three colors in both works. Interestingly, when Fitzgerald met Zelda Sayre in Montgomery, she drove a little white roadster.

I disagree with the answer above in regard to Dexter.  While he does have a distinct disadvantage over Gatsby in that he, at least, remains alive, for all intents and purposes, Dexter is dead.   Notice the way the colors change...in the beginning, of course, everything is cold and white.  Virginal.  As Dexter becomes closer to obtaining what the "thinks" is his desire, the colors become warm and golden.  But in the end, his world is devoid of color. No longer virginal, no longer white, Dexter's physical world reflects his mental state:  grey and lifeless.  Though he lives, his life is over.   

FSF's work is often very autobiographical.  Judy, and later, Daisy, is based very closely on a woman who ditched the author early on, Generva King.  Fitzgerald's insecurities would not improve on meeting Zelda.  Zelda, like Judy, and Daisy, was of a much higher social standing than himself.  He never quite got over the initial snubbings from her well-heeled circles. 

As an aside, FSF once whined to Hemingway, "The rich are different than you and me." Hemingway famously quipped, "Yes, they have more money."  Fitzgerald was never quite convinced of this fact; throughout his life, he longed for the magical quality he thought the rich possessed, even though time and again, like Dexter, the rich would only sorely disappoint him.

If you are writing a paper on this topic, you might find it helpful to visit our page here at eNotes, How to Write a Compare and Contrast Essay. 

Both stories are seem similar at first because they are both about poor young men who fall in love with rich, unattainable, women. Both women lack real values yet both Jay Gatsby and Dexter Green live their lives and attain success in order to win their love. However, Gatsby goes much farther in his pursuit of Daisy Buchanan than Dexter goes in his quest for Judy Jones. Gatsby changes his entire identity, makes up stories about his past. and gets his money through mostly illegal means. Dexter, on the other hand, attends an excellent university and makes his fortune as a successful businessman. He is able to return to his home town and is invited to meet with men for whom he used to caddy. Then he learns that Judy's "beauty and vitality have faded" and he feels empty. But at least he is still young and most importantly, alive. He can still learn from his experience. Gatsby, on the other hand, sacrifices his life for a woman who will never truly appreciate what he has done.