Success

Dexter's vision of success involves a pursuit of the American dream of wealth and status. As Fitzgerald traces Dexter's movement toward this goal, he becomes, in essence, a social historian of his generation, chronicling the dreams of the men and women of the 1920s who saw unlimited opportunities in the new century. Even as a teenager, Dexter dreams of success. While working at a local golf course, he fantasizes about becoming a golf champion and winning matches against the wealthy men for whom he caddies, or dazzling them with his expert diving exhibitions. Later, his dreams involve his movement up into the wealthy class where he would be rich enough to marry Judy Jones. She becomes the embodiment of his ‘‘winter dreams’’ of a glittering world with endless glamour and promise.

Dexter eventually gains wealth and status due to two qualities that are inherent in the American character: hard work and confidence. Even as a young man in his first job, Dexter strives to be the best. At the Sherry Island Golf Club, he is the favorite caddy, due to his devotion to learning and helping others excel at the game. He is such a success in his position that one of the men at the club, ‘‘with tears in his eyes,’’ begs him not to quit. But Dexter is too confident in his abilities to stay in a service position, especially when Judy treats him as her inferior.

Later, he turns his confidence and drive to his education, choosing a prestigious Eastern college over a state school that would have been easier to afford. After college, he dives into the business world, where he learns all he can about running a successful laundry. Soon Dexter achieves his goal: he becomes a wealthy businessman and, as such, catches the eye of Judy Jones. Yet, eventually, he discovers the hollowness that exists at the core of his winter dreams.

Hollowness

Dexter soon confronts the reality of the glittering world of which he has become a part. That reality is embodied in the character of Judy Jones, who has become the focus of his dreams of success and happiness. Underneath the beauty and vibrancy, however, Judy's shallowness and destructive character emerge.

Judy's ultimate goal is the gratification of her own desires, without any concern for those she destroys along the way. As she quickly becomes bored with one suitor, she replaces him with another, yet saves the first for future use. When she decides one of her admirers is beginning to lose interest, she pulls him back into her orbit with promises of fidelity, only to discard him again later. Dexter becomes caught up in this destructive game after he decides she has caused him to be ‘‘magnificently attune[d] to life,’’ to envision her world ‘‘radiating a brightness and a glamour he might never know again.’’ After he enters her world, he and the woman to whom he briefly becomes engaged suffer great pain and disillusionment.

Failure

At one point, Judy glimpses the hollowness of her existence when she admits, ‘‘I'm more beautiful than anybody else … why can't I be happy?’’ Her and Dexter's failure to achieve happiness illustrates Fitzgerald's fundamental criticism of the American dream. At the heart of the dream is an illusory world of glitter and glamour that ultimately contains no substance. While Dexter could have found happiness through a satisfying relationship with Judy, she does not have the strength of character to commit herself to him.

By the end of ‘‘Winter Dreams,’’ Dexter has accepted the failure of his relationship with Judy because he still believes in the glittering dream of her and her world. However, when a business acquaintance tells him that she has lost her youthful beauty and has become a passive housewife to an alcoholic, abusive man, his illusions are shattered. As a result, he concludes, ‘‘the gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time.’’ Ultimately, he grieves not for Judy, but for his lost golden world, ‘‘the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.’’

In being heralded as the “laureate of the Jazz Age,” Fitzgerald struck in his very American writing a balance between romance and disaster, glitter and delusion. His characters include the petted and popular and rich, who both dream and live recklessly and who have as their biggest enemy time, the time that ages and changes. The aging process is signified by the word “winter” in the title, but “winter” also signifies a transition that is more tragic than physical deterioration; by the end of the story, Dexter’s emotions have become frozen. He has lost the ability to care or to feel. His “dream” of Judy had kept him energetic, passionate, and alive, and now the dream has been taken from him.

The reader cares about Dexter at the beginning of the story and wants him to succeed in career and in love. One myth associated with the American Dream is that even the poor, by spunk and luck, have a chance of making it big, and Dexter, whose mother “talked broken English to the end of her days,” has worked hard to raise himself out of the poor immigrant class to which he was born. However, the dream of material success finally proves unsatisfying to Dexter, who comes to know that money cannot buy his real dream. In contrast, Judy was born into wealth and takes it as much for granted as she does her good looks. Judy, the spoiled little rich girl, gets what she deserves. She has been a merciless flirt, using her attraction to break hearts for sport. When the story reveals that she has become careworn and commonplace, married to a bully who deceives her, it is obvious that the tragedy is not hers but Dexter’s, who most wanted not riches, but a woman he could never have. What is the most tragic of all, the woman was not worth having.