With Chatwood, I wonder what his psyche is, his mental toughness?
We know he's got good stuff. And we know the Cubs are pretty comfortable going with wild, inconsistent relievers. And the Cubs think they've got awesome player development, even if that may be self-delusion when it comes to pitchers.
Why they should maybe keep him: His stuff is plenty good. He might thrive as a short reliever, getting used several times a week. A few tweaks to his delivery, some confidence, and you might have a very, very effective relief arm, capable of going >1 inning. And *IF* he did get squared away, you might have a very desirable rotation-replacement, if/when injury necessitates. Also think that obviously nobody is going to claim him and pay him. So I think you've got a fair chance to send him to Iowa and let him regain his confidence, without needing to waste a roster-spot at the beginning. (That chance depends on him not refusing to go, which of course he might. That's partly where his mind-set and psyche and sense of Cub loyalty and trust, or lack thereof, factors.)
Why they shouldn't: Not many Steve Blass recovery guys. May think you've "fixed" it, but the second a pitch or two goes wild, that brain might be going "here we go again", and rebuilt confidence can vanish in a second. So I think it may be much harder to get back to the bad-control Rockies version this second time than it was getting to anti-awful control originally. He didn't have all these crazy bad memories originally. Second, he may not have any Cub loyalty and trust. They had all kinds of ideas to improve him when they got him; major fail. And they had ideas to help him fix, also failed. Plus obviously they lost trust in him; so it wouldn't be surprising if he'd see this as the worst place for him to be, and that he'd reject an Iowa assignment.
Not sure what I think. I kinda feel like trading him will just lock in a loser contract, and that you aren't really going to offset any signfiicant salary. And that it might almost be best to give him another shot; that his chance of becoming useful, slim as that chance is, might almost be less slim than the bad-contract you'd need to take on in order to offload him? If you release him in the spring and eat the contract, not sure that's really going to be any worse than taking on some bad contract and bad player instead.