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The sad state of this offense says we still need two bats so that Ackley and Smoak don't have to to it all themselves.
LF and DH are where those bats need to come from.
If Saunders is gonna be able to post a 110 OPS+ then that counts as decent.  Not great, but survivable.  We can't be getting another 85-90 out of the position.
Same with DH.  The kids have to have room to struggle without feeling like every loss is their fault because they ARE the offense.
Jack knows this.  He needs some players who can be productive from the first April game.  But we can't be trading Smoak or Ackley and taking one of our "add 25 OPS+ points" patches on last year's roster and ditching them for a similar patch.
We need both Ackley and Smoak.  If Upton alone costs us Smoak and Pineda, it's not worth it.  I'm willing to swap pitching help for hitting at this point. 
I'm not willing to just move the hole from the 2nd "easiest" hole to fill to the 3rd.  That's not trading a bat at an offense position for a bat at a glove position.  We might as well have just moved Smoak to the OF and shot Pineda in the leg in the process.
Doesn't make sense.  Which is why I don't expect Jack to do it.
~G