A ruckman, after a single game for Collingwood in the VFA in 1896, the
Benalla-born Flynn started his career in earnest in 1897 where he was part of Geelong's inaugural VFL side. Flynn stayed with the club until the end of the 1902 season when he crossed to Carlton. He was made Carlton captain in 1905, and in 1906 led them to the premiership, defeating Fitzroy in the Grand Final. Due to business commitments in
St James, running the local
hotel (pub) which still operates today (37 kilometres north of
Benalla), he retired from football; however, he returned for the 1907 finals series after captain
Fred Elliott was suspended. Flynn's captaincy was sought after and he led them to another premiership. In 1908, Flynn did not play a game during the home-and-away season but was again used by Carlton in the finals, this time under the captaincy of Elliott, and was a member of a premiership side for the third successive year. He played his last match in Carlton's semifinal of 1910 after three players had been dropped, accused of
tanking in Carlton's upset Round 18 loss to St Kilda. As of 2021, at 39, he is the oldest player to play in a final. Flynn was captain of the St. James Socialables FC that defeated St. James FC in the 1910 Dookie Football Association premiership. He was a member of the 1913
St. James FC premiership that defeated
Yarrawonga in the Yarrawonga and Border Football Association. ==Death==