| 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.
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.