Compare and contrast Dexter's desire for material success with his desire for Judy.

 In F. Scott Fitzgerald’s “Winter Dreams” financial success was Dexter’s ambition but Judy Jones was his obsession. From a young age, Dexter dreamed of joining the ranks of the wealthy men he caddied for at the country club. He wanted to be more than the other young men and proved that by choosing a prestigious college where he was uncomfortable with his lack of spending money. By the time he was in his early twenties, he was well on his way to financial success with his business acumen. His small laundry business quickly grew as did his wealth.

He was invited back to play golf at the country club where he caddied as a boy. It was during this golf game that he was reintroduced to Judy Jones. The obstinate little girl had grown into a feisty, beautiful young woman who broke men’s hearts on a regular basis.

Dexter became a successful, self-made man with the airs that he acquired during his years at university. 

He made money. It was rather amazing. After college he went to the city from which Black Bear Lake draws its wealthy patrons. When he was only twenty-three and had been there not quite two years, there were already people who liked to say: "Now there's a boy--"

Despite his rise, Judy could always bring him to his knees. She was a fickle lover to the many men she dated. For a number of years, he lived for time spent with this illusion of a lover.

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.

Eventually, Dexter became engaged to another young lady who would further his dreams of a stable home life in which his children grew up with the easy attitudes of the rich. On the night before his engagement, Judy comes back into his life. Once again he is drawn to her. He leaves his fiancée and wedding plans to spend one month with Judy Jones.

When their relationship ends on her terms, he sells his businesses and moves to New York City where he easily furthers his financial success. A gentleman from Detroit visits his New York office, and shares news of Judy’s sad marriage to a philandering man. Dexter realizes, although he became a financial success, he failed to reach his dreams.

Even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.