The premise behind not loving the deal depends on one's understanding of player opt-outs, which, for whatever reason, seems to be a very contentious subject on this board.
When you give a player an opt out, you're hoping that he will exercise it. In other words, the Red Sox are hoping that this is a 2/50 contract. If a player does not take the opt out, then it means it was, by definition, a bad deal. This last sentence is the controversial part. For my part, I don't know how it's debatable, but I understand that there are many (many many) on SOSH who disagree with me. (Is it possible that 3/60 will, in 2 years, seem "just about right" such that JDM just takes it and we think, "well, that's about right"? Sure. But looking forward, not in hindsight, the fundamental premise of an opt out is that you're giving the player a guarantee that he will only take if it's good for him, which necessarily means bad for you. At this moment in time, the value proposition is the sum of all possible results multiplied by their expected incidences.)
So, when one says it's a "bad" deal, it's not because one thinks that 2/50 is bad. It's not. 2/50 is great. Heck, 2/60 would have been great. Nor is it that one thinks 5/110 is a "bad" deal. It's not. I would have been delighted with a straight 5/110. Heck, I would have been delighted with a straight 5/120. Because both of those give the team the upside, which is what it's buying for the $110 million or $120 million guarantee. The part that's "bad" about this deal is guaranteeing a guy $110, which is an additional $60 million against injury or being sucky in years 3-5, with no commensurate upside -- other than the upside of thinking he'll be worth more than $50 million over the next two years. If there's upside in years 3-5, or if it looks like there will be at the end of year 2, the Red Sox will not get it. They'll either pay market for it, or some other team will.
What's the upside of getting 2 years for $50 million? Let's say that a very well-constructed valuation of JDM over the next two years puts his value at $65 million, even baking in injury potential. Seems a bit high to me, but whatever. Let's just use it. The question then becomes is the expectation of $15 million in added value over the next two years worth the $60 million guarantee. Reasonable minds can differ over that question, surely. There's a small back and forth earlier in this thread where I think syd and I are basically having an abbreviated version of that discussion. But I don't think it's crazy for someone to say no, it's not worth it. Does that make the deal "bad"? I dunno. I don't want to use a simple word for a non-simple answer. I'm glad the Sox got JDM. I don't think they could have been competitive without him in this division in the next two years. Having stared down what contracts like Panda's, Castillo's, Allen Craig's, and, soon, Price's can do to you, I have some concerns about the opt out portion.