Caylor was also a manager for the Cincinnati Red Stockings of the American Association, succeeding the original manager, Pop Snyder. His stint with the team was mixed, since he finished in second place in his 1885 debut season, but the following year, he finished with a losing record (65–73) and in fifth place. Caylor resigned after the 1886 season due in large part to his combative nature that put him at odds with the press and new club ownership.\n', '

Caylor moved to Philadelphia where he began writing for the Sporting Life. The New York Metropolitans then hired him as their manager on June 11, 1887, with Caylor inheriting a team with a 9–28 record. He was fired in the off-season by new owner Charlie Byrne after finishing the season with a dismal 35–60 record and a seventh-place finish. Caylor\'s career as a manager was over with an overall managerial record of 163–182 (.472 winning percentage).\n', '

Caylor moved to Carthage, Missouri, where he proceeded to start The Daily Democrat newspaper. In 1890, he would move back to New York City after being hired by Albert Spalding to be the editor for the New York Sporting Times.\n', '

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