In 1896, William Randolph Hearst hired Dryden as a writer for the "New York Journal". While working in New York, Dryden gained national fame as a result of a lengthy public quarrel with Andrew Freedman, the owner of the New York Giants. The feud began during spring training in 1898. Dryden asked Freedman for a comment on a player with whom Freedman was in a salary dispute. Dryden published a story the next day making fun of both Freedman and the player, referring to Freedman as "the spurned magnate." Freedman was angered by the account and had Dryden banned from the hotel where the Giants were staying. The next day, Dryden ran an article noting that he had been informed of the ban while trying to put a tablespoon of soup in his mouth at the hotel restaurant. Freedman escalated the punishment by banning Dryden from the Polo Grounds. The next day, Dryden watched the game from Coogan's Bluff, overlooking the Polo Grounds, and reported that "the Giants don't look any better from here." When Dryden continued to make Freedman the butt of his jokes, calling him "Andy" in a series of articles, Freedman announced publicly that "this here feller Dryden had better look out because he's standing on the brink of an abscess [sic] and the first thing he knows I'll push him in." The next day, Homer Davenport published a cartoon showing Freedman pushing Dryden, with his pencil and scorecard, into a black abyss. The Freedman articles were a sensation and reportedly "kept not only New York but the entire country convulsed by [Dryden's] clever quips." In 1900, the publisher of "The North American" (later merged into "The Philadelphia Inquirer") hired Dryden away from Hearst. Hearst reportedly made "exceptional offers" to persuade Dryden to stay, but the Philadelphia newspaper was the high bidder. The Philadelphia Athletics of the early 1900s, with colorful players like Rube Waddell, Ossee Schreckengost, Chief Bender and Socks Seybold, were ideally suited to Dryden's colorful writing style. One colleague recalled, "This team gave Charley Dryden a chance to exercise his talents to their utmost. Story after story was a classic." In one of his most famous stories, Dryden wrote about a "bleary-eyed" Rube Waddell leaving a saloon and jumping into the Delaware River to rescue what he believed to be a drowning woman.