Ambition is one prevalent theme in "Winter Dreams" by F. Scott Fitzgerald.
Dexter Green dreams of breaking free of his humble origins and becoming a part of the society of those who frequent the Sherry Island Golf Club, where he works as a caddy. In fact, it is his encounter with the imperious upper class young girl, Judy Jones, which precipitates this decision to follow the dictates of his "winter dreams," his ill-fated ambitions for the future.
After he quits his subservient job as a caddy in rebellion against his station in life, Dexter also declines a business course at the state university and goes instead to the East. There, at a prestigious university, Dexter entertains the hope of attaining social rank by his association with "glittering things and glittering people." After college, Dexter succeeds in becoming financially successful in the laundry business. However, he desires more in his ambition; so, before he reaches the age of twenty-seven, Dexter sells his business and moves to New York.
But, a couple of years before he sells his business, back in Minnesota Dexter accompanies the men for whom he once caddied in a round of golf at the Sherry Island Golf Club. While on the course, he again encounters the rich girl, whose "passionate quality of her eyes" and her imperious demeanor captivate Dexter. Now she is a young woman of arresting beauty and "passionate vitality." Indeed, Dexter perceives Judy as the embodiment of all that he envies. Therefore, his ambition now becomes the goal of capturing her. For, in doing so, Dexter feels that he will validate his claim as a member of the upper class.
However, this "Winter Dream," like the dream of wealth, proves itself false and costly as the selfish Judy later discards Dexter. For, wealth and social status are hollow dreams that cannot substitute for genuine relationships with people and genuine values that truly bring happiness and fulfillment to a person's life. Thus, Dexter Green's ambitions have been hollow ones.