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The Freshest Boy
tears in last leaf; in very good condition.

Basil Duke Lee at prep school. The original typed title, “The Fresh Boy,” has been crossed by Fitzgerald at the top of page 1 and “The Freshest Boy” substituted in his pencilled holograph. There are extensive corrections and revisions by Fitzgerald in pencil throughout this working draft, ranging from punctuation changes and repagination, through numerous deletions (the crossed out words are easily readable) and the insertion of phrases and sentences, to the ending of the story (four-and-a-half sentences of the printed text) being supplied in the author’s handwriting. Important emendations include the alteration of the names of few characters. In total, there are more than 1,000 words in Fitzgerald’s holograph.

“The Freshest Boy,” one of Fitzgerald’s most anthologized short stories, was first published in The Saturday Evening Post, 28 July 1928 issue; it was collected in Taps at Reveille (1935) along with four other Basil stories and three Josephine (Perry) tales. It is the second in the series of nine stories centering on young Basil Duke Lee, really Fitzgerald himself, which he wrote for The Saturday Evening Post between March 1928 and February 1929.

Malcolm Cowley notes, in his edition of The Stories of F. Scott Fitzgerald (New York, 1986, p. 307): “… the Basil stories … written in 1928 … tell us nothing about Fitzgerald’s emotions at the time, except that he was unhappy about himself and in a mood for retrospection. He relived his boyhood in the stories and made little effort to disguise the fact that he was writing autobiography. Almost every incident happened in life and almost every character can be identified … St. Regis School, where Basil was ‘The Freshest Boy’ [the most unpopular boy], was of course the Newman School; during his first year at Newman [which he entered in September 1911], Fitzgerald was just as miserable as his hero.” In the story Basil Duke Lee, age fifteen, overhears an unhappy conversation between Ted Fay, the Yale football captain and his girlfriend, and “he realizes that life is difficult even for apparently successful people. He thus forgoes a trip to Europe, which would have removed him from his painful school experience, because he is unwilling to give up his dream of ‘the conquest of the successive worlds of school, college and New York’” (Tate, F. Scott Fitzgerald A to Z, p. 92). In his spring term things improve a bit for Basil, though he “was snubbed and slighted a good deal for his real and imaginary sins, and he was very much alone. But on the other hand, there was Ted Fay [the Yale captain], and ‘Rose of the Night’ on the phonograph — ‘All my life whenever I hear that waltz’ — and the remembered lights of New York, and the thought of what he was going to do in football next autumn and the glamorous mirage of Yale and the hope of spring in the air … There would be new fresh boys in September; he would have a clean start next year.”

This typescript has been sold at Sotheby’s auction.

Published in The Saturday Evening Post (28 July 1928).

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tears in last leaf; in very good condition. Basil Duke Lee at prep school. The original typed title, “The Fresh Boy,” has been crossed by Fitzgerald at the top of