Can anyone top 29 years?
1988: Pick 24 (David Hynes)
1995: David Hynes traded to Fremantle for Phillip Matera and pick 3 (Brendon Fewster)
1999: Brendon Fewster traded to Fremantle for pick 16 (David Haynes)
2003: David Haynes traded to Geelong for pick 20 (Sam Butler)
I believe this is the oldest live pick still going around.
I checked 1986 and 87 draft and nothing there still alive so unless some pick in a pre-season or mid-season draft from 86 or 87 is alive you have found the winner.