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Winter Dreams by F. Scott Fitzgerald: Analysis

Fitzgerald wrote his short story “Winter Dreams” while he was drafting The Great Gatsby, which became one of the most celebrated novels of all time. The two works share several thematic and stylistic elements as they each center on a young man from a modest background who strives to be a part of the exclusive world inhabited by the woman he loves. A close comparison of the two works will reveal that while The Great Gatsby becomes a more complex and penetrating critique of the pursuit of the wealth and status, the short story stands on its own as a compelling portrait of a man who is forced to face the illusory nature of his “winter dreams.” 

There are strong similarities between Jay Gatsby and Dexter Green. Although Dexter, unlike Gatsby, came from a middle-class background, (his father owned the “second-best” grocery-store in his town), he subscribes to the same American dream as does Gatsby, who grew up in poverty. Both spent their childhood in the Midwest, and from an early age, were determined to gain entry into the glittering and glamorous world of the rich. Through a combination of ambition and hard work, they achieve their goal and become successful businessmen who are accepted into this exclusive world. 

The process by which they rise to the top, however, is quite different. Fitzgerald clearly outlines the steps Dexter takes to become successful: he attends a prestigious Eastern university and upon graduation learns everything he can about the laundry business. The knowledge he gains, coupled with his confidence and a small financial investment, guarantees his prosperity. Fitzgerald is not as straightforward about Gatsby’s rise. There are suggestions that he may have been involved in a cheating scandal and a bootlegging operation with some shady New York entrepreneurs. Fitzgerald’s inclusion of the possibility that Gatsby may have prospered by his involvement in illegal activities highlights the sense of corruption he finds at the heart of American materialism, a theme he develops more completely in his searing portrait of Tom Buchanan, Daisy’s fabulously rich and morally corrupt husband. 

While both of Fitzgerald’s protagonists start out wanting only the status and power that wealth will afford, they shift their focus to a beautiful woman who embodies their dream and with whom they fall in love. Eventually, each finds little satisfaction in purely materialistic gain. Initially Dexter, like Gatsby, is not a snob; he does not want “association with glittering things and glittering people,” but he does want “the glittering things themselves.” Both men amass fortunes, but their wealth ultimately does not fulfill their dream, which focuses on gaining the love of a beautiful woman who expresses the glamour and promise of that exclusive world. At Gatsby’s extravagant parties, for example, the host retreats to the study, waiting for Daisy to appear, refusing to participate in the hedonistic atmosphere of the gathering. Likewise, Dexter has no social aspirations and “rather despised the dancing men who were always on tap for the Thursday or Saturday parties and who filled in at dinners with the younger married set.” Neither man is affected by the attitudes of others in his pursuit of his dreams, nor does either bear any malice toward the women who repeatedly scorn them. 

Daisy and Judy also are quite similar in character. Each is a shallow, ultimately cold-hearted woman who is entertained, as Fitzgerald describes Judy, “only by the gratification of her desires and by the direct exercise of her own charm.” Like Judy, Daisy enjoys “the mystery that wealth imprisons and preserves, of the freshness of many clothes .. . gleaming like silver, safe and proud above the hot struggles of the poor.” The two male characters have their hearts broken by these lovely women who exhibit “a continual impression of flux, of intense life.” Daisy and Judy are “careless people” who “smashed up things and creatures and then retreated back into their money or their vast carelessness .. . and let other people clean up the mess they had made.” 

Daisy appears to be the crueler of the two, as she allows Gatsby to take the full responsibility for her accidentally running down Myrtle, Tom’s mistress, which results in Gatsby’s murder by Myrtle’s husband. Judy’s only crime is breaking hearts. Readers feel a bit sorry for her when she wonders to Dexter, in a broken voice,”I’m more beautiful than anybody else…. Why can’t I be happy?” But ultimately, Fitzgerald creates a fuller, more sympathetic character in Daisy. 

Through his manipulation of the narrative’s chronology, readers are privy to a demonstration of the intense love Daisy had at one point for Gatsby, revealed when she breaks down in the shower, immediately before her marriage to Tom. Jordan notes how Daisy had to be forced into her wedding dress by her parents, who were determined that their daughter marry so well. Readers also see how she suffers in her relationship with her brutish husband. Fitzgerald portrays Daisy as someone who had the potential for happiness, but was not strong enough to achieve that goal. By the end of the novel, she retreats with Tom into the only world she knows. 

Fitzgerald does not develop Judy into a complete character. Readers never know how she became so callous and shallow, and as a result, they have little sympathy for her, even when they discover at the end of the story that her beauty has faded. Like Daisy, Judy has become a passive wife to an abusive husband, but because readers do not see how that process occurred, as they do with Daisy, her character remains undeveloped and not as interesting as her counterpart. 

The settings of the two works reveal Fitzgerald’s rhetorical brilliance in his poetic descriptions of the landscape. He paints detailed portraits of the landscape that artfully reflect each work’s themes. Throughout much of The Great Gatsby, Fitzgerald concentrates on images that illustrate the corruption at the heart of the American dream. His landscapes become the wastelands of garbage heaps and burned out valleys of ashes. The eyes of Dr. T. J. Eckelberg, a symbol of crass materialism and loss of spirituality, peer down from billboards along the highway. At the end of the novel, however, Fitzgerald presents perhaps the most lyrical passage in literature when he describes Daisy’s green light, representing to Gatsby the possibility of an “orgastic future” with Daisy. 

Fitzgerald’s descriptions in “Winter Dreams” are equally lyrical and resonant. They also reflect the dual nature of the main character’s experience. At the beginning of the story, when Dexter can only fantasize about a golden future, the landscape reflects his depression: the long winter “shut down like the white lid of a box” as he skis over the golf course’s snow-covered fairways. The narrator notes Dexter’s identification with his surroundings when he describes his melancholic response to the links’ “enforced fallowness, haunted by ragged sparrows for the long season” and “desolate sand-boxes knee-deep in crusted ice.” At that period of his life “the wind blew cold as misery” and the sun cast a “hard dimensionless glare.” 

At the beginning of his relationship with Judy, however, when the world is filled with excitement and promise, the landscape dramatically changes. One afternoon, soon after he has run into Judy on the golf course, the sun sets “with a riotous swirl of gold and varying blues and scarlets” and the water turns “silver molasses under the harvest-moon.” 

While Fitzgerald ends the two works with each main character losing the woman he loves, he leads the two in different directions, and as a result, creates two distinct and compelling commentaries on the pursuit of the American dream. As each story draws to a close, Fitzgerald delineates important differences between Dexter and Gatsby. 

At the end of “Winter Dreams,” Dexter accepts the fact that he has lost Judy, and accepts also “the deep pain that is reserved only for the strong” since he had also, “tasted for a little while the deep happiness.” He does, however, receive a shock at the end that alters his vision of the golden world he experienced for a time. When a business associate tells him that Judy has lost her beauty and her vitality, his dream shatters and he breaks down, overcome by a profound sense of loss. Joseph Flibbert, in his critique of the story in the Reference Guide to Short Fiction, argues “As long as he could maintain a vision of Judy as the embodiment of genteel youth and beauty, he could continue to believe in an attainable ideal of power, freedom, and beauty.” The world now becomes cold and gray with no point to the accumulation of material objects. 

Struggling desperately to regain that vision, Dexter tries to picture “the waters lapping on Sherry Island and the moonlit veranda, and gingham on the golf-links and the dry sun and the gold color of her neck’s soft down,” but cannot, insisting, “these things were no longer in the world! They had existed and they existed no longer.” He finally understands that he can never follow the same vision that had compelled him to travel in one direction all of his life. All he is left with now is a sense of emptiness, for “even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.” 

Gatsby, however, dies with his vision of Daisy and the promise of a life with her intact. He never sees Daisy’s beauty fade, nor does he realize that she has returned to the safety of her relationship with Tom. His inability to give up his dream earns Nick’s respect and his conclusion that Gatsby was “worth the whole damn bunch put together.” Gatsby becomes a mythic figure in the novel, the tireless pursuer of the American dream—the “fresh green breast of the New World.” Fitzgerald’s closing lines reinforce this mythic dimension when Nick notes Gatsby’s inability to see through the illusion and so remain devoted to his vision of Daisy. Nick echoes this enduring sense of hope in the novel’s last lines as he insists that although happiness eludes people, “tomorrow we will run faster, stretch out our arms farther…. So we beat on, boats against the current, bourne back ceaselessly into the past.” 

Fitzgerald’s exquisite crafting of these two works has created enduring portraits of characters whose fate expresses a deep resonance of the American experience. Through Dexter Green, Fitzgerald has chronicled the journey of a realist, who forces himself to shatter the illusions he has held for so long. In his creation of Gatsby, Fitzgerald presents the romantic, who refuses to give up his pursuit of the woman he loves, who represents to him, all that is possible in America. 

Source Credits:

Carol Ullmann (Editor) Short Stories for Students: Presenting Analysis, Context & Criticism on Commonly Studied Short Stories, Volume 15, F. Scott Fitzgerald, Published by Gale, 2002.

Wendy Perkins, Critical Essay on “Winter Dreams,” in Short Stories for Students, The Gale Group, 2002.

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