As a teenager, what daydreams does Dexter Green have about the men he caddies for?
Because he comes from a solid middle class family, it is asserted early in the story that Dexter Green caddies only "for pocket money." He does, however, daydream about beating the wealthy patrons who play the country club at Sherry Island. He fantasizes that one day he will be a "golf champion" and beat Mr. T.A. Hedrick, a rich man who frequently plays the course. In some scenarios he beats Hedrick easily "with almost laughable ease" and sometimes "he came up magnificently from behind."
Like Gatsby in Fitzgerald's most famous work, Dexter wants money, but more than that, he wants to feel as though he is better than the rich he caddies for on the golf course. Later in the story he actually plays with Hedrick, commenting that "he was impressed by the tremendous superiority he felt toward Mr. T.A. Hedrick, who was a bore and not even a good golfer any more." It is during this round of golf that Dexter once again meets Judy Jones after, in a comic scene, she hits Hedrick in the stomach with a golf ball, casually saying she was sorry before playing through with little regard for the man.
Dexter dreams of not only beating the men at golf in marvelous fashion, but he also dreams of living their glamorous lifestyles and experiencing their almost worshipful admiration of him (similar to his own admiring perspective of their lives and fame).
Fitzgerald includes this description at the beginning of the story when Dexter bemoans winter's effects on the fairway, and so instead, in his mind,
"he became a gold champion and defeated Mr. T.A. Hendrick . . . [or he steps] from a Pierce-Arrow automobile . . . [or he strolls] frigidly into the lounge of the Sherry Island Golf Club"
as he is surrounded by admirers or gawked at by Mr. Mortimer Jones (another golfer). Dexter's dreams about what life would be like as the idle Old Money golfers demonstrate that possessing a lot of money is not his objective; rather, he wants the fame, superiority, and seemingly effortless effect that belong to the men for whom he caddies.