Pickett rejoined Port Adelaide from the North Melbourne Football Club, where he played after being recruited from Port Adelaide Magpies in the SANFL. He was an immediate success, winning the Rising Star Award and playing in the 1999 Premiership. He returned to Port Adelaide as part of a trade in 2003, and was an immediate success playing in a more forward role than he had played at North Melbourne. In 2004 he was an integral member of the Premiership winning side, playing an outstanding game against Brisbane Lions, which saw him win the Norm Smith Medal as best afield in the Grand Final, picking up 20 possessions and booting 3 goals. His career at Port Adelaide finished at the end of 2005, after which he was traded to the Melbourne Football Club.
2003-2005 Statistics:Games: 55
Goals: 80
Average kicks: 8.40
Average handballs: 3.07
Average disposals: 11.47
Average marks: 3.38
Average tackles: 2.44
Total Brownlow votes: 8