In October 1926, Bush was hired to replace Bill McKechnie as manager of the Pittsburgh Pirates. The Pirates were loaded with talent but had finished in third place in 1926. In Bush's first year in Pittsburgh, he led the 1927 Pirates to a National League pennant with a 94–60 record. The Pirates were then swept in the by the 1927 New York Yankees in the World Series. During the 1927 season, Bush had a feud with Pirates star Kiki Cuyler. Cuyler was unhappy about being switched from third to second in the batting order, and he allegedly slackened his effort for a few games. Bush reacted by benching Cuyler in August and not playing him again for the rest of the season, even keeping him out of the World Series. Bush ignored chants from Pirate fans, "We want Cuyler! We want Cuyler", in the games at Pittsburgh. After the season, the Pirates traded Cuyler to the Cubs.