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Tasmanian Len Pye played his early football in the VFA with Northcote before starting his North Hobart career in 1929. Strong in the air, Pye often played the role of an on baller. He won a William Leitch Medal in 1932 and in doing so became the first player from his club to win it. The previous year he won the first of his four North Hobart 'Best and Fairest' awards, with the others coming in consecutive seasons from 1936 to 1938.
Pye was a member of North Hobart's 1936 premiership winning side to go with his previous premierships in 1929 and 1932. He was voted 'Best on Ground' in the 1936 decider, as well as the Grand Final the subsequent year which they lost. Two further premierships followed and he finished his career as a five time TANFL premiership player and with three Tasmanian State Premierships. From 1935 to 1941 the league didn't award a Leitch Medal, instead handing out the George Watt Memorial Medal to the season's best player, which was Pye in both 1937 and 1938.
After not playing during the war he returned for another stint at North Hobart in 1946. The following year he decided to join New Norfolk for their inaugural TFL season and he spent two years with the club before retiring.