In our U.S. History Shmoop learning guide on the 1920s, we talk about the huge rise in consumer culture at this stage of the twentieth century. Well, "Winter Dreams" was published in 1922, right at the start of the Roaring Twenties. Fitzgerald is clearly responding to the sudden, visible signs that lots of Americans are getting very rich, very quickly. Dexter Green's ease with making money demonstrates both the positives (yay! cash!) and the negatives (boo! bad human relationships and loss of romance!) of this sudden rise in American wealth. The obvious and visible class differences between the very rich and the middle class are what drive Dexter to succeed at any cost, even if it means losing the romantic idealism of his boyhood.
Dexter gets that being part of the upper class is about more than having money: after all, he insists on attending an elite college and dressing perfectly for his first dinner date with Judy.
Mortimer and Judy Jones' disrespectful behavior towards the people is Fitzgerald's way of telling us that wealth kills your sympathy for others.
Dexter strongly associates money with love in "Winter Dreams." He thinks that if he has money, he can win the love of Judy Jones. One tiny problem: he doesn't get that having money might somehow replace love in his emotional life. So when he dedicates himself to earning money, his ability to love dies away without him even knowing it. He is left instead with "the gray beauty of steel that withstands all time" (6.35). Not even the loss of Judy can get to him. The great irony of Dexter's life is that, as a boy, he links money and love together. But in Fitzgerald's world, money and love are actually mutually exclusive. No one who has a real talent for making money can hang on to their romantic ideals.
By making Judy Jones a two-dimensional character, Fitzgerald emphasizes that Dexter's attraction to her is not personal, but just a symbol of his desire to achieve upper class status.
Dexter's character in "Winter Dreams" suggests that love and desire for money are incompatible. For Fitzgerald, it appears that business success kills off human feeling.
Dexter is not ambitious just for the sake of making tons of money. The narrator of "Winter Dreams" is careful to remind us that there is nothing "merely snobbish in the boy" (2.1). Dexter is an idealist: he associates cash with the graceful, attractive lives of the members of the Sherry Island Golf Club. In fact, making money is almost secondary to his main ambition of leaving behind his humble origins and joining the upper class. (Take, for example, his embarrassment: "His mother's name had been Krimslich. She was a Bohemian of the peasant class and she had talked broken English to the end of her days. Her son must keep to the set patterns" [3.2].) Dexter dreams of starting a new family, in which his children won't have to worry about being of the right class or stock. Money is a way to make that better life possible, but it's not a goal in itself.
Dexter's effortless financial success allows Fitzgerald, as a writer, to downplay the difficulties of earning money. That way, "Winter Dreams" can focus instead on the major emotional problems that accompany business ambition.
Dexter's ambition does him more harm than good. After all, he ends up miserable and alone.
Dexter is a man of action, a self-made man who can change his life by going to an elite college and investing cleverly in business. But he can only do those things because he is, specifically, a man. Judy Jones has the same kind of restless, melancholy spirit that Dexter does. But because she is a pretty lady, she becomes an object to be admired (by men like Dexter). Her great talent is her physical beauty, and it is through her body that she tries to find emotional fulfillment. What is this, the 1920s? Oh. Yeah, it is.
The other main female character in "Winter Dreams," Irene Scheerer, represents another possible, socially acceptable role for upper class women in the 1920s: wife and mother. Irene is welcoming, friendly, and clearly destined to be great with her kids. While in many ways, Judy and Irene seem like absolute opposites, they share the same essential trait. Their characters are defined in relation to the story's central male figure, Dexter. We have no sense of how Judy and Irene think as rounded characters. The fact that they are women limits their ability to move through multiple social spaces the way that Dexter can.
Judy is a total diva. But her assumption that beauty means (or should mean) happiness is just the 1920s female equivalent to Dexter's belief that money means happiness.
Judy is looking for the same kind of emotional fulfillment from her many partners that Dexter seeks in his business investments. Their two separate responses to the same feeling of loneliness and isolation is the result of gender difference.
Memory and the past are everywhere in "Winter Dreams." Heck, the "Tone" of the story is wistful and nostalgic. On the one hand, Dexter wants to forget his humble origins. He wants to leave behind the memories of his immigrant mother and his grocer father, move to the East Coast, and make tons of money. Dexter's social success depends on his willingness to ignore his lower class background so that he can attach himself completely to the upper class. On the other hand, Dexter's eagerness to leave behind his social origins shows that he also has to sacrifice his own early memories. To make lots of money, he also has to turn his back on the romantic idealism of his younger days. Dexter appears perfectly fine with forgetting about his parents. (Nice, Dex.) But he weeps when he finally understands that he has also cast aside "the country of illusion, of youth, of the richness of life" (6.36) that used to inspire him so much. He has forgotten about the boy he used to be, which is the worst loss that Dexter can imagine.
"Winter Dreams" uses Dexter Green's sense of distance from his own past to show off the general flexibility of the American class system. (I.e. Dexter can go from humble immigrant parents to a future in which his children can afford "carelessness" [3.2] in just three generations.)
Dexter spends so much time in the past and the future that he forgets about the present moment. He would have had a more fulfilling life if he'd remembered to live in the moment.