After winning the 1994 Swan Districts Best & Fairest award, Gerard Neesham saw him as a natural selection for Fremantle's inaugural squad for the 1995 AFL season. Neesham was right as Callaghan became a star in his 5 years at the club, being nominated for the AFL Rising Star award in both 1995 and 1996 and finishing in the top 5 players of Fremantle's best and fairest award three years in a row between 1996 and 1998.[1]
St Kilda
In 2000 the Dockers traded Callaghan to St Kilda in exchange for Matthew Carr. Callaghan's time at the Saints was marred by injury, spending two of his four years sidelined by knee injuries.[2] So in 2004 after only 29 games for St Kilda he decided to retire from AFL football.[3]
Swan Districts
Callaghan returned to Western Australia to again play in the WAFL for the Swan Districts. He announced his retirement on 22 July 2006, due to another knee injury.[4]