Before the 1921 season, the media questioned whether Hooper would re-sign with the Red Sox for the coming season, saying that Hooper may have been disappointed not to be given an opportunity at manager. Since 1919, Red Sox owner Harry Frazee had been getting rid of expensive veteran players in what has been called a "fire-sale". Hooper was traded to the Chicago White Sox in March 1921 in exchange for Shano Collins and Nemo Leibold. Newspaper accounts said that Hooper had not been warned about the trade, that he would demand a higher salary from the White Sox and that he was prepared not to play unless the team met his demands.