Playfair grew up in and played his junior football with Holbrook[1] in the Riverina region of New South Wales.
Playfair was an integral part of the Cats 2007 VFL premiership team, along with players such as Charlie Gardiner, Brent Prismall and Tom Lonergan.
Playfair retired as a player at the end of the 2010 season due to injury concerns, but continued his involvement with football and with the Sydney club, being appointed as a development coach.
[4] After suffering a serious back injury in the Round 14 match against Richmond at the SCG, and after medical advice Playfair decided to call an end to his career as an AFL player.
[6] Playfair then spent two seasons with St Kilda Football Club as backline and team defence assistant coach.