One of Dexter’s motivations for caddying, beyond the pursuit pocket money, is related to his desire to achieve success greater than that of most people in his Minnesota town. His feelings about his station in life can be seen in Fitzgerald’s use of imagery early in the story, when Dexter is detailing his feelings during the cold months:
The country gave him a feeling of profound melancholy—it offended him that the links should lie in enforced fallowness, haunted by ragged sparrows for the long season. It was dreary, too, that on the tees where the gay colors fluttered in summer there were now only the desolate sand-boxes knee-deep in crusted ice.
In contrast, he viewed Sherry Island, where he caddied, as a place where dreams came true. In the fall, when the beautiful colors of summer had faded, he would play out summer victories in his imagination:
He became a golf champion and defeated Mr. T. A. Hedrick in a marvellous match played a hundred times over the fairways of his imagination, a match each detail of which he changed about untiringly—sometimes he won with almost laughable ease, sometimes he came up magnificently from behind. Again, stepping from a Pierce-Arrow automobile, like Mr. Mortimer Jones, he strolled frigidly into the lounge of the Sherry Island Golf Club—or perhaps, surrounded by an admiring crowd, he gave an exhibition of fancy diving from the spring-board of the club raft.
Dexter‘s ambitions play a central role in Winter Dreams, and caddying serves as a launching pad for the rest of his life.
Dexter in F. Scott Fitzgerald's "Winter Dreams" "caddied only for pocket money" (Fitzgerald, 1). Dexter does not need to caddy, because his father "owned the second best grocery-store in Black Bear" (Fitzgerald, 1). However, he is the best caddy at the club, and the money is good. He is often requested by some of the better golfers at the club, and "the thirty dollars a month he earned through the summer were not to be made elsewhere around the lake" (Fitzgerald, 2). Dexter does not really need the money, though, and so he decides to quit one morning right in the middle of his shift.
For the other caddies, however, this is not just a summer job or a hobby but money that they desperately need. The opening of the text explains that "some of the caddies were poor as sin and lived in oneroom houses with a neurasthenic cow in the front yard" (Fitzgerald, 1).
https://public.wsu.edu/~campbelld/engl494/winterdreams.pdf
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