After working for the
Louisville Evening Post for a year and a half, he returned to his hometown to edit the
Paducah Democrat. In 1900 he married Laura Spencer Baker of Savannah, Georgia, who urged him to try his fortune in New York. In August 1904 he took his wife and infant daughter to Mrs. Cobb's parents, borrowed two hundred dollars from his father-in-law, and headed for fame and fortune in the big city. It was not long in coming, but it took some plotting on his part. After spending two weeks in fruitless search for a job and seeing his borrowed finances shrink to three dollars, he devised a stratagem that Benjamin Franklin would surely have approved. In the factual but flippant style that was to become his hallmark, Cobb sent identical letters to the editors of thirteen leading New York papers, informing them that he was tired "of studying the wallpaper designs" in their outer offices and wanted an opportunity to present his qualifications in person. He concluded: "A modest appreciation of my worth forbids me doing business with your office boy any longer."
From the five offers of work he received, he accepted a job with the Evening Sun.
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