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Jackson grew up in Cronulla, New South Wales and attended De La Salle College before transferring to St. Joseph's College, Hunters Hill where he commenced his rugby career. In 2006 Jackson toured to Dubai with the under 19s Australian Team to compete in the world championships. This team was the first Australian team to ever win the world championships in this age group. In 2006 he also made his representative rugby debut for the NSW Waratahs scoring two tries against Saracens. In 2007 he played 4 games on the wing for the Perth Spirit and 2 games for the Sydney Fleet in the Australian Rugby Championship. He is currently a 1st grade rugby player for the Southern Districts Rugby Club. From 2008 he appeared as 'Outlaw' in Gladiators (Australian TV series).