Middle-class Dexter Green has big dreams—to one day be as elite as the "old-money" families he works for each day as a golf caddy. When Dexter returns to the golf club as the guest of the men he once caddied for, he meets his undoing in the enchanting Judy Jones.

First published in Metropolitan Magazine in 1922, F. Scott Fitzgerald's "Winter Dreams" was considered by the author to be the first draft of The Great Gatsby. It is his most popular and republished short story within the Gatsby-cluster.

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