Pitt began playing senior SANFL football for Norwood in his late teens.
[1] As the SANFL is semi-professional, Pitt had a day job a police officer,[1] but he continued to play senior and reserves football for Norwood.
Despite an impressive first AFL season,[2] Pitt opted to leave Collingwood to go back to South Australia, to continue working as a police officer.
[4] Pitt again drew the eye of AFL recruiters at the age of 26, when he won Norwood's best and fairest award for the 1999 season.
[8] Pitt had decided to give his AFL career another chance, as he felt that he had left Collingwood prematurely.