In F. Scott Fitzgerald’s short story “Winter Dreams,” the links at Sherry Island represent the hopes, dreams, and ambitions of Dexter Green. Sherry Island is significant because it is the place where the rich and privileged spend their summers socializing and playing golf. It is an exclusive group to which Dexter aspires to join.
Each Autumn, Dexter allows himself to dream about becoming a golf champion on the links, a masterful swimmer, and a member of the ranks of those who he caddied for. He would be respected and admired for his athletic skills, and he would have material wealth. Dexter would not be the caddy ordered about by a rich, young girl, instead he would be her equal. He equated happiness with the lifestyle on Sherry Island.
As Dexter matured he made life choices that allowed him to attend a prestigious college, and start successful businesses....
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His position in life allowed him to go back to the Sherry Island links where he was invited to play golf by those he caddied for as a boy. He was able to attain the Sherry Island lifestyle he coveted, but was he happy? His material success did not translate into a fulfilled personal life.
October filled him with hope which November raised to a sort of ecstatic triumph, and in this mood the fleeting brilliant impressions of the summer at Sherry Island were ready grist to his mill. 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. . . . Among those who watched him in open-mouthed wonder was Mr. Mortimer Jones