I was looking the other day at pick 6 in 2012, with which we have secured Jackson Macrae. This was a compensation pick for losing Callan Ward. We drafted Callan Ward in 2007 with pick 19, the pick which we got from Richmond in exchange for Jordan McMahon. McMahon was drafted with pick 10 in 2000.
So essentially, we traded pick 10 in 2000 for pick 6 in 2012, plus 174 games of service (114 games from McMahon and 60 from Ward).
What are some other long strings of trades you can think of?