Dexter's real reason for quitting his caddying job is that he's deeply affected by his first encounter with the young Judy, and he has to do something about these strong feelings right away:
But he had received a strong emotional shock, and his perturbation required a violent and immediate outlet.
Judy's overwhelming beauty and charm, along with her brutal and bratty behavior, have captivated Dexter. He can't properly express his feelings of shock and bewilderment, so he channels those feelings through the only outlet available to him: his power to quit his job.
Yes, it's a strange thing to do, for several reasons. Dexter is excellent at his job, it pays him better than other available jobs would, and he is respected and valued there. To a casual observer, there is no good reason for Dexter to quit and every reason for him to continue caddying.
His boss, Mr. Jones, even asserts that Dexter is an intelligent, honest, and grateful boy, with a good work ethic. It's out of character, then, for Dexter to not only quit his job with no notice but also to lie about why he is quitting. He tells Mr. Jones that he's become too old to be a caddy, but that's an excuse.
What this episode shows us is that Judy holds an unnatural power over Dexter. Without even trying, she's caused an upheaval in his young life: it's a pattern that will continue through the rest of the story.
Why does Dexter quit his job in "Winter Dreams"?
Dexter quits working as a caddy in F. Scott Fitzgerald's short story "Winter Dreams" when he is at the top of his game. Dexter is known as the best caddy at the club, but after seeing Judy Jones and her nurse on the course, he is motivated to quit. He makes this decision during a cold spring, and the decision scares him. He knows that he cannot make up the money he earned caddying other ways, and, but Fitzgerald writes about Dexter, "he had received a strong emotional shock, and his perturbation required a violent and immediate outlet." Part of the reason he quits is that he is shocked by how lovely and perhaps cruel Judy Jones appears, even at the age of 11, and he knows that he wants to be her equal rather than caddying for her in a servile role.
In addition, as Fitzgerald writes, "It is not so simple as that, either. As so frequently would be the case in the future, Dexter was unconsciously dictated to by his winter dreams." Over the winter, Dexter has dreams of "ecstatic triumph." He dreams of becoming a golf champion and stepping from a luxury car into the golf club, while others look at him with envy. In the spring, he realizes that his reality has fallen far short of his winter dreams, and he decides to quit his job to create a new and more majestic reality for himself.
Why does Dexter quit his job in "Winter Dreams"?
So much of people's lives are spent measuring themselves against others. In Part I of...
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"Winter Dreams," Dexter waits in the caddy-shack on the orders of Mr. McKenna who tells him to wait until the caddy master has returned. While he is waiting, a nurse and her ward, an eleven-year-old girl, the daughter of Mr. Mortimer Jones, have come so that the child can play golf. When Dexter refuses to caddy for them because he must attend the shop, and he informs them that there are no other caddies available, Miss Jones and the nurse go outside, where the girl slams her club on the ground with violence and an argument ensues between the child and her nurse.
As soon as the nurse sees the caddy-master she inquires if someone cannot now caddy for them.
"Well?" The caddy-master turned to Dexter. "....Go pick up the young lady's clubs.""I don't think I'll go out to-day," said Dexter."You don't----""I think I'll quit."
Although "the enormity of the decision frightened him as the thirty dollars a month he earned was not available anywhere else nearby, " Dexter is changed, and he feels he must react:
"...he had received a strong emotional shock, and his perturbation required a violent and immediate outlet."
This is the first of what Fitzgerald calls Dexter's "winter dreams," his dreams of being rich and having the privileges attached to this wealth. Little Judy Jones's actions have given Dexter a new direction in life in the illusions of his youth for which he will later suffer as he has become enamored of her and lets her represent all that he thinks he wants.
Why does Dexter quit his job in "Winter Dreams"?
In the beginning, Dexter quits his job as a caddy because of Judy. While he works at the golf course, he is proud of moving up to being the most sought after caddy of the place. He is not there to make a living. His earnings are merely pocket change for him, as his father is a wealthy businessman. He dreams of success, even as a teenager. He dreams of becoming a golf champion and showing up all of the golfers there at the course. However, that pride is quickly wounded when the eleven-year-old Judy Jones comes to play at the golf course. He quits his job at this point. She treats him as an inferior. That makes him want to be even more successful than he originally planned. His aspirations for a successful future slowly come to include Judy as his potential wife. He wants all of the "glitter," "glamour," and "promise" that she could offer him with his wealth.