Jim Flynn

Originally a Benalla product who managed a solitary VFA appearance for Collingwood, Jim Flynn spent the first six seasons of the VFL establishing himself as a serviceable but unspectacular follower with Geelong. His career trajectory shifted dramatically in 1903 when he was lured to Carlton by the club's new secretary and coach, Jack Worrall. Worrall saw leadership potential in the veteran ruckman that others had missed, installing him as captain in 1905. The decision proved a masterstroke, as Flynn became the on-field general for the Blues' first golden era, skippering the club to back-to-back premierships in 1906 and 1907.

Flynn was a versatile big man, capable of rucking all day or marshalling the troops from centre half-back with his intelligence and sure hands. His later career was defined by a reluctant brilliance; battling the demands of running his hotel in St James, he attempted to retire multiple times, only for Worrall to talk him back into the side for finals campaigns. This unique arrangement saw him return to play in the 1908 premiership side, and famously, he was summoned one last time at age 39 for the 1910 semi-final after the club was rocked by bribery allegations against star players. He remains one of the oldest players to ever contest a VFL/AFL final.