CSF77
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People need to slow their roll on Lackey. They aren't going to cut him. This is a team already bumping up against the luxury tax so you don't just throw away a guy who's costing you $8 mil or so for the rest of the year. They almost certainly will ride his contract out. This is especially true when you have no idea on Hendricks' status.
As for Doolittle I don't really see the point. Uehara is effectively a LHP with his splits. Dunesing has been pretty good in Wood's low leverage role. And I'm not really sure Montgomery is better in the rotation anyways. Having someone you can confidently send out for 2-3 innings is a huge deal. It allows you to save your other bullpen guys. Plus, if you're assuming they trade for Gray, you're going to have Arrieta, Lester, Gray, Lackey + one of Hendricks and Butler. Obviously that's Hendricks if healthy but as mentioned we don't know. Point here being, you don't need to use Montgomery in the rotation. If you wanna rest the starters when rosters expand and use Montgomery as a 6th starter than sure go for it.
I'd be greatly opposed to trading more resources on another reliever because they still have yet to solve their starter situation going into 2018. Ok sure if you get Gray that helps but Butler/Montgomery aren't sure things. And you still have to replace Lackey. I'd prefer they save their resources because Gray is already going to cost a ton and you may need some prospects for other stuff such as that other starter.
I'm pretty sure Mike starts the rest of the year and Butler goes to AAA when Kyle gets back. If they trade for a SP it will be to replace Lackey who is ineffective and not on the roster.
That way they would have Lackey, Hendricks, Montgomery and (say Grey) then they can targe Darvish in the off season.
Now yes they have issues with not having a high leverage middle relief. They have Edwards and Grimm right now from the right side but a guy like Doolittle comes with 2 years of control and is a pitcher that can change momentum.
The other guy I'm thinking of is Hand from SD who is in that role also.
Sure you could take a conservative approach and keep Montgomery in the pen and just target Grey or they can do that and set up for the future.