"Winter Dreams" is the story of the rise of Dexter Green, a hardworking, confident young man who becomes caught up in the pursuit of wealth and status, which is why he began working as a caddy in the first place. At fourteen, Dexter is described as the best caddie in the club, making thirty dollars a month, which for the summer "was not able to be made anywhere else on the lake". He wanted to be close to and eventually become a part of what all the golfers were--the glittering things. As the story says, "He wanted not association with glittering things and glittering people--he wanted the glittering things themselves".
After going to college in the east, despite his father's offer to pay for the state college, Dexter opens a chain of laundries, and slowly began to become successful in the world of business.
Dexter considers Judy Jones to be a glittering thing.
He is quite foolish in that he wants to be with Judy. Dexter should have seen what Judy was doing to the other men in her life, and he should have left her. However, Dexter did not leave her, and he ends up hurting other people because of his foolishness, namely Irene, his fiancÃÂ©e. Dexter finds out from Devlin that Judy is now married to Lud Simms, a man who "ill-uses her, drinks, and runs around". Knowing this, as soon as Judy Jones enters Dexter's life again and shows the slightest interest in him, he broke off his engagement with Irene. In the end, he winds up with neither woman, and his dream no longer exists.