We'll actually find the answer within the first sentence of the story:
"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-store in Black Bear--the best one was 'The Hub,' patronized by the wealthy people from Sherry Island--and Dexter caddied only for pocket-money."
What this means is that, because Dexter would like a little...
We'll actually find the answer within the first sentence of the story:
"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-store in Black Bear--the best one was 'The Hub,' patronized by the wealthy people from Sherry Island--and Dexter caddied only for pocket-money."
What this means is that, because Dexter would like a little extra money for himself so that he can spend it on whatever he wants, he does the work of a caddy.
What's a caddy? Also spelled "caddie," it's someone who works at a golf course, helping the players by carrying their equipment around for them and talking to them as they play. This job can be done by young teenagers, since it doesn't require a lot of skill.
Like you might guess, caddying is not a very glamorous job. And Dexter's thoughts reveal, at the end of Section I of the story, that he only earns $30 per month while working full-time in the summer. Since the story takes place in about 1922, that would be like only earning about $400 in today's money, which is really a small amount in exchange for laboring for the entire month!
Dexter is only about fourteen, so he can't really get a higher-paying, more respectable job that requires a full high school education--yet. For now, caddying is a good option. Of course, the story of how he quits is how "Winter Dreams" really begins.
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