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.