Cleary played as a fullback and won two best and fairest awards for South Melbourne, in 1942 and 1944.

He was a highly regarded player, and attracted lucrative offers – an undisclosed amount from Brighton in 1940,[2] and £400 from Camberwell in 1945[3] – to cross to the Victorian Football Association during the throw-pass era, but chose to remain with South Melbourne.

Cleary's reputation as a fair player earned him the nickname "Gentleman Jim";[4] this did not stop him from being suspended for eight matches for a striking offence in the notoriously violent 1945 VFL Grand Final – in an incident team-mate Laurie Nash later described as "one of the few honest accidents in the game".

[6] He remained involved in the game even after retiring as a coach, becoming a regular panelist on World of Sport.

This Australian rules football biography of a person born in 1914 is a stub.