It can work in your favour to not do so. Especially if you can get a ready made player that is a must have for your list and a pick back as well.
Like Saints pick5 - basically into Carlisle and Gresham. Both now in their best 22.
Gaining a 20-24yr old player whose already had a number of years development and proven themselves helps push up the ladder faster.
Depends how far along list rebuild you are as to whether do it or not.
JJ and pick 15 off Dogs for pick5 is a no brainer IMO, especially if that pick 15 then got used on Hopper for example. Two insta-best 22 players.
Dogs would want more though. Gleeson would end up in mix as a replacement HBF.