Prior to assuming the managerial job with the Browns, Diddlebock had never played or managed in the major leagues. He was the head sportswriter for The Philadelphia Times for eleven years and held the same position at The Philadelphia Inquirer for six years. He was the longtime president of an organization known as the Scorer\'s Association, and he was a horse racing official. He also covered the famed 1892 fight between boxers John L. Sullivan and James J. Corbett.\n', '

Within baseball, Diddlebock variously served as president, secretary and treasurer for the Eastern League, a minor league that served as one of the precursors to the International League. He later held financial interest in a team in the Pennsylvania State League, which became a rival of the Eastern League.\n', '

In December 1895, he was hired as the manager of the St. Louis Browns for the 1896 season by the team\'s owner, Chris von der Ahe. The Browns and their owner were held in low regard at the time. Sportswriter Alfred Henry Spink wrote that "Mr. Diddlebock\'s mission will be to repair the damage Von der Ahe has done the game and the St. Louis club." Newspapers in St. Louis were initially supportive of Diddlebock, but before he took the field, the team was embroiled in controversy when it was announced that they would spend $30,000 to bring in five star players from Philadelphia. The Browns did not have the money to finance such a deal, and von der Ahe blamed Diddlebock for the story that had gotten out.\n', '

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