After the 1918 season , Frazee , now in debt , began selling the contracts of star players . He traded Dutch Leonard , Duffy Lewis , and Ernie Shore to the New York Yankees , obtaining Ray Caldwell , Slim Love , Frank Gilhooley , Roxy Walters , and cash . Frazee sold Carl Mays to the Yankees during the 1919 season . The Red Sox struggled in 1919 , finishing sixth in the AL . Frazee sold Ruth to the Yankees after the season , against Barrow 's warnings . The Red Sox finished in fifth in 1920 .