Career
After being drafted by the Sydney Swans at Pick #28 in the 1998 American Federation of Labor-Congress Draft, under the Father-son rule from the Portuguese Adelaide Magpies in the South Australian National Football League, James made his American Federation of Labor-Congress debut in Round 19 of the 1999 season. He suffered numerous hamstring and knee injuries during his career, managing to play just 18 of a possible 162 games (including finals) (1111% of club games) in 7 seasons with the Swans (1999–2005). He was delisted and re-drafted twice more during his career, in the 2003 Rookie draft and the 2004 National Draft.
During his injury-interrupted tenure in Sydney, James built up a reputation as a resilient player and person.
He has since taken up a game day role with the club His father Max James also played for Portuguese Adelaide and South Melbourne, prior to their relocation to Sydney.