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Hidden in brief and cryptic entries in his ledger and notebooks, the story of Fitzgerald’s encounter with Mary Harriman Rumsey, one of the most powerful women in America during the author’s lifetime, has gone largely unnoticed. In addition to helping Fitzgerald discover the lifestyle of the moneyed aristocracy of Old Westport, Long Island, and their involvement in the movement of eugenics as material for “The Great Gatsby,” Mary Harriman Rumsey shaped the author’s view of the very rich and won his applause for her work in New Deal politics. Fitzgerald’s assessment of her role in breaking away from the traditional behavior of her class is reflected in his “Count of Darkness” stories, strengthening the argument that these stories can be read as political allegory and commentary on the Depression and the New Deal. There is a parallel, moreover, between the protagonist’s humbling and that of the author, each leading to recognition of the power of women and their role in politics. Full appreciation of all documentary evidence supports the argument that Fitzgerald’s portrayal of “the pretty woman in a brown riding habit” in a scene in chapter 6 of The Great Gatsby is a lasting memorial to Mary Harriman Rumsey.