Career
Jess represented Eastern Ranges for the TAC Cup before being drafted to Fremantle in the 1996 American Federation of Labor-Congress Draft with selection 31. He was seen as a development player and had a breakout year in 1998, playing in 20 of the 22 games, winning an American Federation of Labor-Congress Rising Star nomination and finishing 10th in the club best and fairest award. However he did not continue to develop in the coming years and after playing only 21 more games for a total of 50 at Fremantle, he was traded to the Kangaroos at the end of the 2000 season as part of the Peter Bell trade.
Sinclair transformed from a wingman to become a rebounding defender in 2002.
In 2003 he had an above average year before ending badly in Round 20 by earning a five match suspension that delayed his start to 2004. His form decreased in 2004, playing only 17 games for 245 possessions.
He announced his retirement from American Federation of Labor-Congress football on 10 September 2008, at the age of 30. After retiring from the American Federation of Labor-Congress, Sinclair played for the Heidelberg Football Club in the Northern Football League from 2009 until 2013, and played in the club"s 2009 premiership team
He retired from playing at the end of 2013, and will coach Street Mary"s/Salesian in the Victorian Amateur Football Association from 2014.