March 4, 1921: Traded by the Boston Red Sox to the Chicago White Sox for Shano Collins and Nemo Leibold. After Boston owner Harrison Frazee sold off most of his star players, including Babe Ruth, Hooper was determined to get his just dues. In 1919 and again in 1920, Hooper held out for more money, but after agreeing to a contract, was dealt to the White Sox prior to the 1921 season for Shano Collins and Nemo Leibold, both outfielders. Both of those players best years were behind them and the deal turned out to be a good one for the ChiSox, who got five solid years from Hooper.

Hooper was often known for his defensive skills and he was among the league leaders in defensive categories such as putouts by a right fielder. During several seasons with Boston, he teamed up with Duffy Lewis and Tris Speaker to form the Golden Outfield, one of the best outfield trios in baseball history. Hooper is also one of only two members of four separate Red Sox World Series championship teams (1912, 1915, 1916, 1918). He was elected to the Baseball Hall of Fame in 1971.