Beginning as a reporter on the
Paducah Daily News, by nineteen he was the paper's managing editor and a correspondent for several big city newspapers, including the
Chicago Tribune. In 1898 he worked briefly for the
Cincinnati Post and then for the
Louisville Evening Post, contributing a humor column, "Kentucky Sour Mash," which included political satire, comic verse, and descriptions of Kentucky's violent, hotheaded rebels--a stereotype later repudiated in his fiction. In 1900 he married Laura Spencer Baker of Savannah, Georgia, and he returned to Paducah the following year as managing editor of a new paper, the
Daily Democrat. Even as a young reporter he was noted for an astonishing memory, a prodigious capacity for work, and a striking ability to flesh out the details of a story from a minimum of facts.
In 1904, at the age of twenty-eight, he sent his wife and daughter to her parents and set out to conquer New York. After two completely frustrating weeks, he wrote a witty form letter to the managing editor of every paper in the city, informing them that "I was probably the liveliest reporter and the best writer and the ablest editor that had ever come to New York to uplift its journalism to the highest possible level, and yet nobody had jumped at the unparalleled opportunity of hiring me." The response was several job offers, from which he chose the Evening Sun .
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