[7][8] His career was marred by unfortunate knee injuries; the first came in 1965 in St Kilda's semi-final victory, which meant Oakley missed the Grand Final.
He suffered déjà vu in 1966, missing not only the Grand Final, but St Kilda's first VFL premiership.
During his time with the VFL/AFL, he was deeply involved in mergers; his administration believed that eleven Victorian clubs, many of which were in a poor financial state, was unsustainable in a national competition.
However, these merger attempts caused great off-field discord among clubs and fans, and the strategy was abandoned after Oakley was succeeded by Wayne Jackson as CEO at the end of 1996.
[citation needed] He is a former Adjunct Professor at Deakin University's Faculty Business and Law,[14] where he also lectured.