Managerial Career
Following the departure of Frank Brettell, Jack became player-manager of Plymouth Argyle in 1905, 1905–06, and led the club to third in the Western League and fifth in the Southern League. He left the club in the summer to take up the position of player-manager at Southend United. In his first two seasons with Southend they won the Southern League Second Division title, gaining election to the Southern League First Division in 1908.
He retired as a player at the end of the 1909–10 season and re-joined Plymouth Argyle as manager, remaining in charge at Home Park until April 1938 when he retired. During his 28 seasons in charge, Jack had guided Argyle to the Southern League title in 1913 and into the Football League in 1920. In their first season in the league they finished 11th in the Third Division, but finished runners-up in all of the next six seasons. They finally clinched the title and promotion in the 1929–30 season. In total, he took charge of 1,093 matches for the "Pilgrims".
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