Background
His father, Jim O'Brien, was a former St Kilda football player.
His father, Jim O'Brien, was a former St Kilda football player.
An Old Xaverian, O'Brien played for St Kilda's thirds and Under-19s sides before joining Collingwood. In the final round of the 1985 VFL season, O'Brien played his first and only game for Collingwood, against Carlton at Waverley Park. O'Brien joined Brisbane in 1987 and after a couple of quiet seasons kicked 19 goals from eight appearances in 1989.
He played just five times in 1990 but had a memorable game against the Sydney Swans at Carrara when he kicked a career best seven goals. A year later, in what would be his final season, O'Brien made 12 appearances and kicked 26 goals. His tally was the equal third most by a Bear for the year and included six goals against Fitzroy.
The following year he represented Victoria at the Amateur football carnival in Adelaide and kicked eight goals in the final to win the Hugh Millard Medal. This included a five goal haul in a four point win over St Kilda, which he won for his team with a soccered goal from 30 metres out late in the final quarter.