Shires broke into the majors on August 20, 1928 with three singles and a triple off Red Ruffing. Cocky and brash, he embodied the Jazz Age twenties. Appointed team captain in 1929, Shires became involved in fist fights with manager Lena Blackburne on two occasions that season, once after refusing to discard a red felt hat which he wore to the plate during batting practice, and once when discovered drinking bootleg whiskey in his Philadelphia hotel room. During that first winter of the Depression, Shires arranged a number of professional boxing matches for himself, and he won all but his contest against George Trafton, center for the Chicago Bears. His challenge of crosstown rival Hack Wilson and fears that Shires might become involved with gamblers led Commissioner Landis to intervene in Shires’s boxing career, and Shires retired from the ring. After demanding a $25,000 contract for the 1930 season, Shires was traded to Washington on June 16 and was out of baseball by 1932.