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Gambling, particularly on craps or horse races, was a common theme of Runyon's works, and he was a notorious gambler himself.One of his paraphrases from a well-known line in Ecclesiastes ran: "The race is not always to the swift, nor the battle to the strong, but that's how the smart money bets." A heavy drinker as a young man, he seems to have quit drinking soon after arriving in New York, after his drinking nearly cost him the courtship of the woman who became his first wife, Ellen Egan. His best friend was mobster accountant Otto Berman, and he incorporated Berman into several of his stories under the alias "Regret, the horse player".Perhaps as confirmation, Runyon was inducted into the writers' wing (the J. Taylor Spink Award) of the Baseball Hall of Fame in 1967.
To New Yorkers of his generation, a "Damon Runyon character" evoked a distinctive social type from the Brooklyn or Midtown demi-monde.His expertise was in covering the semi-professional teams in Colorado; he even briefly managed a semi-pro team in Trinidad, Colorado.At one of the newspapers where he worked, the spelling of his last name was changed from "Runyan" to "Runyon", a change he let stand.When Berman was killed in a hit on Berman's boss, Dutch Schultz, Runyon quickly assumed the role of damage control for his deceased friend, correcting erroneous press releases (including one that stated Berman was one of Schultz's gunmen, to which Runyon replied, "Otto would have been as effective a bodyguard as a two-year-old.").Runyon's marriage to Ellen Egan produced two children (Mary and Damon, Jr.), but broke up in 1928 over rumors that Runyon had become infatuated with Patrice Amati del Grande, a Mexican woman he had first met while covering the Pancho Villa raids in 1916 and discovered once again in New York, when she called the American seeking him out.