His first managerial job came in 1884 with the Milwaukee Brewers of the short-lived Union Association (it only lasted one year), in which he only managed 12 games (going 8–4).
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In 1890, he was hired to manage the Cincinnati Reds, who had recently made the jump from the American Association to the National League.
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His playing career began in 1877 with the St. Louis Brown Stockings of the National League, but he only played in nine career games in 1877 and 1883 as an outfielder.
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He left the game after the 1891 season, but he came back to manage the Chicago Orphans and the Washington Senators, and in each of his managerial stops, he would have part ownership of the team.
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