 Massie moved to Aston Villa in December 1935, but was unable to prevent their first ever relegation at the end of the 1935–36 season.Massie retired from playing at end of the 1944–45 wartime season, and was appointed manager of Aston Villa in August 1945 and lead them to top ten finishes in his first three seasons, despite not having complete control of the playing side of things at Villa Park, and twelfth place the following year.However, in August 1950 he left Villa.