But in the potential restructure, is it conceivable that the Red Sox could offer him more, and not seek the least expensive path? I guess the calculation is that JD was considered to be worth his original contract value. Could his relative value have increased to some level beyond what the Red Sox would have considered acceptable when they first signed him?
Sure, but why does he need to renegotiate with the Red Sox now? If he thinks he's worth more, and can get more, I'm sure the Red Sox are one of the teams he'll want to talk to when he's a free agent.
The one part of all this that is unclear to me is to what extent is Boras required to be acting in the dark during this period. I'm sure there have been some innuendo type conversations here and there, but I doubt that Boras has been able to go into full blown sell mode, and I doubt that competing G.M.s have been willing to have freewheeling negotiation type conversations with him. (Unless the Red Sox have given permission, which I expect we would have heard about if it happened.)
So, that adds a level of uncertainty for JD, in that he has to guess what his market will be. That's the only thing the Sox have going for him that might make them want to try to enter into an extension with him now. But otherwise, even if you really like the player, it doesn't make sense for the Red Sox to do it now. Let's say they value him right now at 4/90. (Just saying for argument, the numbers don't matter to the point.) At this point, maybe he elects not to opt out, and you've won. And even if he opts out, you still can offer him 4/90 after he does so and see if it gets it done. The only circumstance in which making the offer now doesn't backfire is if it prevents him from opting out and you could have saved a few pennies.
I guess the other thing that extending him now does is that it locks him up without you having to worry about opt outs the next two years. But, I think the Sox are in pretty good position right now. They may get a very good hitter for 3/63 and if they don't, they have $63 million to spend over the next 3 years to improve, whether by putting that same amount toward a new JD contract or something else.