Let's put it a simpler way: I think they're losing value in both trade #1 and trade #2. #1: I know some have really soured on Baez thanks to his contact rate issues, but I still think he's more valuable in a trade than almost any pitcher, including Ross. CJ for Grandal also seems like a value sacrifice, so if we're giving up value twice to dump Wood, I'd almost rather just dump Wood for nothing, then. #2: I don't see the value in trading Castro at all, especially if they aren't getting a better player in return, which I'm not sold on for either Harvey or Syndergaard. If they're already trading Baez, there's especially no reason to trade Castro unless the return blows you away, which it doesn't on its own, let alone adding assets to send with him. As for the rest, Headley is a valuable asset if there's a need there, which there'd only be if you're creating one by dumping the existing plan. Jackson for Crawford...sure, I'd rather have Crawford as a 4th OF than Jackson as a 5th SP...but that Crawford contract goes on longer and I'm not sure how much use the Cubs would have with a 33 year old corner OF that's best asset is speed.