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.