I'd keep Dempster and then trade him rather than sign Drew, add $10 million in cost and probably lose a pick as a result. I wouldn't sign Drew even at $5 mil. At $4.9 mil though he would have a deal! And then I would probably trade Middlebrooks!
To me it is very important for every GM to create "value". If they play Middlebrooks and Bogaerts they have a chance to add a tremendous amout of "value" to the roster. Why is that important? Well, consider what happens when you make a trade. If you have more value on your roster, you can get back more in a trade.
For example, if KC had held onto Myers and Odorizi, they probably would have created more than $100 mil in player value instead of what happened when they traded them for 2 years of $10 mil type control of James Shields and 4-5 years of control of Wade Davis. Most analysts in hindsight think they got hosed:
What if we had sat Iglesias in AAA rather than given him a chance in mlb. Well we never would have gotten Peavy back in return if that had happened.
No doubt that sometimes a prospect will fail and you get relatively little value out of them but the chance of a hit prospect like Myers is so big that often letting them play is better. And you could make a strong case that Middlebrooks in not at optimum value right now but he may be worth a small fortune if he comes back anywhere near his rookie year levels.
Consider the situation with Bogaerts. For God's sake let the kid play and let him add value like the projected ROY candidate he is likely to be. He's this year's potential Will Myers. And some here want to lose a pick, lose $10 million in revenue and reduce his potential value proposition?
I don't get it at all.