What is Dexter's motivation for being a caddy in "Winter Dreams"? How does this make Dexter different from some of the other caddies?

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In the opening lines of "Winter Dreams," the narrator observes the key difference between Dexter Green and "some of the caddies" who "were poor as sin." Dexter "caddied only for pocket-money" because his father was a successful merchant and his family was solidly upper middle-class. For some of the other caddies, the pay and tips they received from members of the golf club were necessary for their survival. For Dexter, caddying at the Sherry Island Golf Club was a means to a different end.

Dexter Green quits caddying at the age of fourteen because he realizes, at this young age, that he does not want to be, or be perceived as, a servant to the upper class. He wants to not only join the ranks of the members at the golf club, he wants to surpass them financially and socially. On the day he quits the golf club, Dexter is partially motivated by his desire to have Judy Jones not see him as beholden to the people who pay him thirty dollars a month.

At this point in his life, Dexter has had a front row view to the lives of the privileged people he serves. He is able to take stock of his life and understand that to rise and become the man he thinks he wants to be, he must strike out of his own.

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The short story "Winter Dreams" by F. Scott Fitzgerald tells of a middle-class boy from Minnesota named Dexter Green. He has a dream of being wealthy and well-respected. The story follows his life for several years as he caddies for golfers at a golf club, attends college, and then finds wealth in the laundry business. One of the main focuses is on his relationship with a gorgeous socialite named Judy Jones who he first meets at the golf club when she is only 11 years old.

Dexter's motivation for being a caddy, as explained at the beginning of the story, is to make "pocket-money." His father owns a prosperous grocery store in the town of Black Bear and presumably takes care of Dexter's basic expenses. This means that Dexter can use his caddy money for whatever he wants. In contrast, some of the other caddies are "poor as sin" and live in one-room houses. In such a situation, their caddy money would be essential and they would not be able to even think of quitting.

However, one of the story's essential plot points hinges on Dexter's loose attachment to his job. Because he is merely earning pocket money and his income is not essential to the survival of his family, he has no real need to work and can quit his job if he decides to. Young Judy Jones shows up at the golf club and calls for a caddy, but after seeing the way she treats her nurse, Dexter refuses to do work for her. He quits rather than act as a caddy for Judy because he does not want to be in a position of subservience to her.

As Fitzgerald puts it, "Dexter was unconsciously dictated to by his winter dreams," which include being wealthy, talented, and prestigious. These dreams become the motivation for many of Dexter's decisions as he proceeds through life. Caddying for Judy would not have fit with his ambitions in life, so he sacrifices his job for the sake of his long-term goals.

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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.

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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).

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