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ALL the deadline deals were.
Jack looked at his underperforming roster and his minor league talent.  His burning questions:
1) If Guti, my prize acquisition, is really cooked, then what in the world are we doing in CF going forward?  And I'm low on outfielders of any stripe after seeing Wilson and Peguero in action.
Answer: Halman scared him and Saunders was looooooost, so he went out and added an emergency CF with power (Wells) AND traded for a truer CFer with some contact issues who was a bit like another Halman in AAA (Trayvon).There was nobody else in the minors to do it and only Ichiro in the bigs, and neither moving him nor paying him were certain things after this year.  Adding Chiang to the OF depth was another move to shore up this uncertainty.
2) My bullpen is sad-sack and needs life, and I have Pineda, Felix, Vargas, Paxton, Taijuan and my newly minted arm from the draft.  The bullpen arms I spent all of last draft acquiring are still a year or two away.  What kind of solution can I make?
Answer: add two good pen arms, one righty and one lefty. The righty has some decently nasty stuff, and as a bonus, the lefty can start (or bridge) so you get flexibility there.
3) My third base situation has been killing this team.  What are my options?
Answer: I don’t believe in Seager at the position and don’t want to place bets on him yet even though I’m rocketing him up the minor-league ladder, Liddi scares me, Figgins and his thousand yard stare is useless… can I help plug this hole so I don’t have to move another SS or 2B over to 3B and suffer there?  Enter F-Mart.
4) I don’t want to trade any of the crown jewels of the system to help patch all these concerns, but Vargas and Beavan have no value.  Pineda only goes for a world-class talent, Paxton on his own wouldn’t bring back multiple major-league ready players...and Fister is pitching out of his mind right now.  Who can I trade to patch the holes?
Answer: The one that annoyed me.
I get why he did it.  I got it at the time.  But yes, I think he'd do it over if he knew that he'd have to bite the bullet on a Pineda trade in order to get a decent offensive force in here over the offseason.
If I tell you now that Carp (whom he'd demoted in irritation at his attitude or whatever already by trade-time) looks like a corner gem, Seager can probably handle 3rd, Guti will be heathy and able to post average CF production (fingers crossed) and we're bursting with pen arms from the offseason...
Then yeah, it seems like some unnecessary convolutions to add depth to this team instead of true talents.
But if we're still scrambling over Guti and Seager and some of our pen arms don't work out...
It makes more sense.  He's got to down-side plan.  Can't just hope for the best results.  Our stoploss players were stopping NOTHING.  I just remember Oakland trading their Big Three and getting lots of returns, and see how smart they were since Zito and Mulder and Hudson all got injured after...
And I see where they are now. I don't want to be Oakland - and at least they squeezed all the juice from that fruit before they traded it.  We just gave up 9 combined years of club control for our #2 and #3 pitchers.  Hultzen and Paxton are very good arms, but are unlikely to exceed what Pineda and Fister were doing.  We're not saving money on the risk either.
So the parts we got back have GOT to be an improvement over what we had. 
A lot rests on Montero, but also on Wells, Ruffin, Furbush and F-Mart.  I need Jack's eagle-eye for talent to be right again - and for us not to be too conservative in deploying that talent.
~G