How we cite our quotes: (Section.Paragraph)
Quote #1
Some of the caddies were poor as sin and lived in one-room houses with a neurasthenic cow in the front yard, but Dexter Green's father owned the second best grocery-story in Black Bear – the best one was "The Hub," patronized by the wealthy people from Sherry Island – and Dexter caddied only for pocket money. (1.1)
This opening passage establishes the class politics for the rest of "Winter Dreams." There are boys at the golf course who caddy because they are "poor as sin," but Dexter isn't one of them. At the same time, Dexter also isn't one of "the wealthy people from Sherry Island." By Black Bear, Minnesota standards, Dexter is middle-class. However, as we find out over the course of the rest of Section 1, middle-class isn't enough for him: he wants to rise to high society status. He wants it all.
Quote #2
"The best —— caddy I ever saw," shouted Mr. Mortimer Jones over a drink that afternoon. "Never lost a ball! Willing! Intelligent! Quiet! Honest! Grateful! —" (1.10)
For Mr. Jones, a caddy should be willing, intelligent, honest, and above all, grateful. The class dynamics in this statement are subtle: a caddy is someone who gets paid to pick up golf balls and carry clubs around. It's a job, like any other service position. But Mr. Jones wants the caddies to be grateful for the opportunity he is giving them to help him out on the golf course. Why shouldn't Mr. Jones be grateful to the caddies for saving him the trouble of carrying his golf clubs? Since Mr. Jones is the rich guy in the golfer-caddy relationship, he thinks his money should be buying him instant obedience and gratitude from the caddies. Jerk.
Quote #3
Miss Jones and her retinue now withdrew, and at a proper distance from Dexter became involved in a heated conversation, which was concluded by Miss Jones taking one of the clubs and hitting it on the ground with violence. For further emphasis she raised it again and was about to bring it down smartly upon the nurse's bosom, when the nurse seized the club and twisted it from her hands.
"You damn little mean old thing!" cried Miss Jones wildly. (1.34-5)
This scene between Judy and her nurse (who, in this context, is Judy's nanny) demonstrates the horror of class differences between rich and poor in "Winter Dreams." Judy is eleven, but because she's a spoiled brat, she gets to shriek at her nurse and whack her with a golf club without much in the way of punishment. The nurse grabs the club, sure, but there are no consequences for this little tantrum. After all, the nurse is a Jones family employee, and Judy is like her boss. Thanks to her family's money, Judy is a powerful little eleven-year-old.
Quote #4
Next evening, while he waited for her to come down-stairs, Dexter peopled the soft deep summer room and the sun-porch that opened from it with the men who had already loved Judy Jones. He knew the sort of men they were – the men who when he first went to college had entered from the great prep schools with graceful clothes and the deep tan of healthy summers. He had seen that, in one sense, he was better than these men. He was newer and stronger. Yet in acknowledging to himself that he wished his children to be like them he was admitting that he was but the rough, strong stuff from which they eternally sprang. (3.1)
Dexter is fully aware that Judy has other lovers. He also has a definite image in his mind of what kind of men they are: prep school guys. Here, Fitzgerald is setting up an interesting distinction between Americans with old money – who "entered from the great prep schools with graceful clothes and the deep tan of healthy summers" – and Americans who make their own fortunes. Dexter is a self-made man, "newer and stronger" than these sons of well-established families. But he also wants his own children to join that elite class of people with old money. It's not enough to be rich; Dexter also wants his family to be socially accepted by the upper class. Basically, he wants to have his cake and eat it, too.
Quote #5
Then, as he turned up the street that led to the residence district, Judy began to cry quietly to herself. He had never seen her cry before. (4.58)
There is something about Judy that is hard and untouchable. But here, as Judy tries to persuade Dexter to come back to her at the end of Section 4, she cries. This weeping makes her seem more vulnerable and human to Dexter. Why do you think she cries at this moment? What emotions could Judy be feeling here?
Quote #6
For the first time in years the tears were streaming down his face. But they were for himself now. He did not care about mouth and eyes and moving hands. He wanted to care, and he could not care. For he had gone away and he could never go back any more. The gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time. 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. (6.35)
For Dexter, Judy's aging is physical proof of the fact that dreams just don't last. His childhood dreams of playing golf with T.A. Hedrick have all come true long ago. He has achieved all the material success he could possibly want. But what has happened to Dexter as a person? He has lost his ability to feel. All he has left is "the gray beauty of steel that withstands all time." He has become a mechanical force for making money. Fitzgerald suggests that achieving your dreams means losing emotion in favor of wheeling and dealing. He doesn't even care about Judy anymore – he's totally lost his ability to care.