Dexter's dreams in "Winter Dreams" are dreams of having a better life and rising above the station that he was born into. He dreams of being a golf champion, stepping from an expensive automobile and into the fancy club, of being respected and admired. They're the dreams of youth but also what push him forward to make money and create a life for himself.
Dexter grew up in an area where he and his family—along with others in their social class—catered to the wealthy who live nearby. This meant that he came close to wealth but didn't have it himself. His winter dreams focus on the kind of wealth he wants to achieve and the symbols of the social status he desires. The dreams and his desire for the "glittering things" drive Dexter so that he attends a prestigious college and makes a lot of money.
At the end of the story, he finds out that Judy Jones, the wealthy object...
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