How does Dexter's character relate to the theme of success in "Winter Dreams"?

Quick answer:

Although Dexter is clearly the central character in "Winter Dreams", it is important to note that there are a number of other characters who all have their own roles to play. Dexter's mother, for instance, is always behind the scenes, but she is clearly the one who has provided his ambition and drive to succeed. And then there is Judy Jones, who represents everything that Dexter wants most: her beauty, her status in society and even the way she dresses. When we first meet Dexter he has already set up his own laundry firm and seems to be very successful. However when Judy Jones dumps him for another man whom he calls a "clown" he feels that his dreams have been shattered forever.

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One of the aspects of contemporary society that Fitzgerald always seemed to write about, at least to some extent, is the American Dream. Here, in this story, clearly Dexter is an excellent example of somebody from more humble roots who, by hard work, manages to get ahead and become part of the "new wealth" of society. He is clearly described as being different from the "old wealth" (those who inherited their wealth rather than earned it):

All about him rich men's sons were peddling bonds precariously, or investing patrimonies precariously, or plodding through the two dozen volumes of the "George Washington Commercial Course," but Dexter borrowed a thousand dollars on his college degree and his confident mouth, and bought a partnership in a laundry.

Note how Dexter is compared to the "rich men's sons" who seem to be rather ineffectual in terms of actually going out there and earning money. Dexter, on the other hand, shows that he is "newer and stronger" by his get-up-and-go spirit.

However, apart from his ability to make financial success come true for him, what is interesting is that his "winter dreams" have focussed on attaining Judy Jones, not just becoming wealthy:

It did not take him many hours to decide that he had wanted Judy Jones ever since he was a proud, desirous little boy.

To him, Judy represents the confidence and carelessness of the wealthy. Note key descriptions of Judy that associate her with gold, such as "a slender enamelled doll in cloth of gold." Fitzgerald is keen to associate her person with the dream of wealth and success that inspires Dexter to quit his job at the beginning of the story.

However, unfortunately, Dexter's "winter dreams" are doomed to failure. When he hears of the loss of Judy's beauty, it appears that he himself experiences his own loss of innocence and youth. As Dexter himself says, "That thing will come back no more."

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