“Winter Dreams” illustrates how social class defines people’s lives, often with unfortunate results. Dexter Green, the story’s protagonist, is a fourteen-year-old caddie and the son of a small-town Minnesota grocer. However, Dexter is determined to become one of the wealthy men for whom he works at the Sherry Island Golf Course. These ambitions are “dictated to [him] by his winter dreams.” These “dreams” to possess “glittering things and glittering people” (the people and objects that he associates with being wealthy) are a metaphor for the American dream of economic success and social prestige. In the story, the American Dream, or the “winter dream,” is an endless—and ultimately unfulfilling—pursuit based on external standards of success and happiness.
Dexter’s pursuit of his “winter dreams” compels him to model himself after wealthy people: he views wealth as the only valid measure of success. Thus, it is significant that Fitzgerald begins the story by describing Dexter’s position in the social hierarchy, indicating that this is the most important thing to know about him. Although Dexter is working as a caddie, he is careful to mention that the other caddies “were poor as sin and lived in one-room houses,” whereas his father “owned the second best grocery-store” in Black Bear, Minnesota. Dexter provides this information because it is important to him that people know that his earnings are “pocket-money,” and not a source of his family’s income. Dexter notes that what separates his father’s store from “The Hub”—the best grocery store in town—is that the latter is “patronized by the wealthy people from Sherry Island.” Dexter’s opening thoughts on class suggest that this is a community that operates according to a strict class hierarchy, and that, at least according to Dexter, the “best” things are those desired by the wealthy.
This belief influences his decision to “pass up a business course at the State university” in favor of attending “an older and more famous university in the East” which costs much more. He associates the East with the world of “old money,” firmly entrenched in American enterprise. As the son of a bohemian in the “new money” Midwest, Dexter thinks that the “old money” culture will legitimize him. However, Dexter never overcomes his obsession with hierarchy. Just as he was aware of his father’s grocery being “the second best,” he notices his relative poverty at the elite university. Therefore, Dexter’s new experiences encourage him to “[reach] out for the best” or, to fit in among even wealthier people than those in Black Bear.
Despite Dexter’s notion that wealth makes one person better than another, Fitzgerald demonstrates that class affiliation has little to do with one’s true nature and more to do with the self-image that person projects. For example, Dexter tries very hard to appear wealthy. He wears clothes from “the best tailors in America” because he is not yet confident enough in his social position not to worry about sending the wrong message to other members of his class. His projection of the image of a perfectly-tailored man is meant to disguise his mother’s lowly, foreign origins.
Furthermore, it is only Dexter’s own inflating sense of superiority—rather than the vapidity of his performance of wealth—that gives him insight into the ways in which other wealthy people might not be as fabulous as he once thought. After achieving success with his laundry, Dexter recognizes T.A. Hedrick, the most prominent golfer on the Sherry Island Golf Course and a wealthy citizen, as rather mediocre at the sport and a “bore.” Though he is not yet as wealthy as the others, Dexter feels a “tremendous superiority” over Hedrick who, due to Dexter’s recent success, seems less impressive than before. However, Dexter’s newfound ability to see through T.A. Hedrick does not make him question whether the more rarified forms of wealth and status that he seeks might be similarly vapid—Dexter’s class obsession only allows him insight that puffs his ego, not insight that might readjust his priorities.
Dexter’s lack of self-awareness regarding his conflation of wealth with desirability is perhaps clearest when Judy Jones, Dexter’s love interest, breaks up with a man because she finds out that he is poor. Instead of making Dexter wary of Judy or aware of his own shallowness, he only desires her more. He “frankly” informs her that he is “probably making more money than any man [his] age in the Northwest.” This news “brought her closer to him, looking up into his eyes.” Dexter’s value is, thus, confirmed by Judy’s willingness to look at him and to be pleased with him because she knows he is rich. Dexter is unbothered by her fickle relationships with other men, perhaps because they are all wealthy, which places him in good company. He has become someone Judy would desire—one of the “glittering people.”
In the end, like “the snow that hid the fairways of the golf course,” Dexter’s “winter dream” evaporates. After he learns that Judy’s youth has faded and that she entered an unhappy marriage, he realizes that the “glittering things and glittering people” cannot sustain him. He can no longer retreat to them or to their memory to find something to care about. Thus, he cries for the first time in years, but only for himself and for the “thing” that was in him which “will come back no more.” Fitzgerald’s characterization of the dream and its loss suggests that Dexter never had a self-defined motivation, nothing outside of Judy and materialism, to give him purpose.
Related Themes from Other Texts
Class Mobility and the American Dream ThemeTracker
Class Mobility and the American Dream Quotes in Winter Dreams
Some of the caddies were poor as sin and lived in one-room houses with a neurasthenic cow in the front yard, but Dexter Green’s father owned the second best grocery-store in Black Bear—the best one was “The Hub,” patronized by the wealthy people from Sherry Island—and Dexter caddied only for pocket-money.
He became a golf champion and defeated T.A. Hedrick in a marvelous match played a hundred times over the fairways of his imagination, a match each detail of which he changed about untiringly—sometimes he won with almost laughable ease, sometimes he came up magnificently from behind. Again, stepping from a Pierce-Arrow automobile, like Mr. Mortimer Jones, he strolled frigidly into the lounge of the Sherry Island Golf Club—or perhaps, surrounded by an admiring crowd, he gave an exhibition of fancy diving from the spring-board of the club raft….
“I think I’ll quit.” The enormity of his decision frightened him. He was a favorite caddy, and the thirty dollars a month he earned through the summer were not to be made elsewhere around the lake. But he had received a strong emotional shock, and his perturbation required a violent and immediate outlet. It is not so simple as that, either. As so frequently would be the case in the future, Dexter was unconsciously dictated to by his winter dreams.
Now, the quality and the seasonability of these winter dreams varied, but the stuff of them remained. They persuaded Dexter several years later to pass up a business course at the State university—his father, prospering now, would have paid his way—for the precarious advantage of attending an older and more famous university in the East, where he was bothered by his scanty funds…. He wanted not association with glittering things and glittering people—he wanted the glittering things themselves. Often he reached out for the best without knowing why he wanted it—and sometimes he ran up against the mysterious denials and prohibitions in which life indulges. It is with one of those denials and not with his career as a whole that this story deals.
He did not consider it necessary to remark that he had once carried Mr. Hart’s bag over the same links, and that he knew every trap and gully with his eyes shut—but he found himself glancing at the four caddies who trailed them, trying to catch a gleam or gesture that would remind him of himself, that would lessen the gap which lay between his present and his past.
One minute he had the sense of being a trespasser—in the next he was impressed by the tremendous superiority he felt toward Mr. T.A. Hedrick, who was a bore and not even a good golfer anymore.
Next evening while he waited for her to come down-stairs, Dexter peopled the soft deep summer room and the sun-porch that opened from it with the men who had already loved Judy Jones. He knew the sort of men they were—the men who when he first went to college had entered from the great prep schools with graceful clothes and the deep tan of healthy summers. He had seen that, in one sense, he was better than these men. He was newer and stronger. Yet in acknowledging to himself that he wished his children to be like them he was admitting that he was but the rough, strong stuff from which they eternally sprang.
He could have gone out socially as much as he liked.... His confessed devotion to Judy Jones had rather solidified his position…. Already he was playing with the idea of going East to New York. He wanted to take Judy Jones with him. No disillusion as to the world in which she had grown up could cure his illusion as to her desirability.
A sort of dullness settled down upon Dexter. For the first time in his life he felt like getting very drunk. He knew that he was laughing loudly at something Devlin had said, but he did not know what it was or why it was funny. When, in a few minutes, Devlin went he lay down on his lounge and looked out the window at the New York sky-line into which the sun was sinking in dull lovely shades of pink and gold.
