Winter Dreams

Dexter Green caddies at the Sherry Island Golf Club outside the Minnesota lakes town where he grew up. He is fourteen, the son of a small grocer, and is good enough at the job that the members tip him well. One spring day a girl of eleven appears on the practice green, swings a club at her nursemaid, and demands a caddy. Her name is Judy Jones. The encounter lasts five minutes; the imprint lasts a lifetime. Dexter resigns the caddy job on the spot rather than have her ever see him in uniform again, and the rest of the story tracks the long, gleaming, half-resigned arc of his life — through college in the East, through a successful laundry business, through a doomed engagement to a sensible girl, through a series of evenings on Judy Jones's porch when she chooses to call him.

Fitzgerald wrote Winter Dreams in 1922, three years before The Great Gatsby, and described it himself as a kind of first sketch of Gatsby's emotional architecture. Both stories work the same territory: the romantic intensity of an unreachable woman, the financial striving meant to bridge the gap, the gradual recognition that the woman herself was never the real object — the dream of the woman was. But Winter Dreams ends in a different key, less elegiac and more bewildered, when Dexter, years after losing track of Judy, hears from a casual acquaintance what has become of her, and discovers that he has lost not the woman he wanted but the capacity to feel what wanting her once felt like.

Winter Dreams rewards readers who want to see Fitzgerald's signature insight in concentrated form: that desire in America is structured around objects that cease to exist the moment they are obtained, and that the saddest losses in his fiction are the losses of the ability to grieve them. The final paragraph is one of the most quoted in twentieth-century American short fiction, and the story as a whole is the indispensable bridge between Fitzgerald's early Saturday Evening Post stories and the masterpiece that was to follow.