Maile is not a prospect.
Tulo and Pillar are not supplanting anyone.
So basically your argument is for Tellez. And I think the board has already established that Morales would be someone to trade away if possible.
It's not like I'm against trading Pillar, but then you have to find someone better and/or cheaper on the FA market which I don't think is really that easy of a task like you make it out to be.
I agree, but this is the whole thing. The team's TOP priority should be securing starting pitching. I don't know how many miracles you expect from this team, but in your universe it sounds like they need to:
1. Dump 5 guys.
2. Pick up 2 SP.
3. Pick up an OF, maybe even a second one now because you created a hole dumping Pillar.
So that's 8/9 moves made, before addressing the bullpen, and all done on a budget (maybe down to 6/7 moves if Smoak/Pillar bring in players addressing the other issues). That's a very, very high expectation of the FO for this offseason.