My thoughts...
He makes a really good point. The sox don't hesitate to throw long term deals to other players. If I were him, and I'm looking around my clubhouse, and I'm seeing half these guys on the DL, the other half not producing, and they're secured with long term deal... yeah, I'd have a little resentment.
He had a couple rough years there, and it got to the edge a couple yrs back, but he's really bounced back. He shows up in spring, he's healthy, in shape. He's taken on a leadership role with the team. This guy is doing everything you could hope him to do, and is the sole representative for the sox at the ASB.
He needs to retire a Red Sox. Lets make sure that happens... I'd offer him a 3yr deal worth up to $36M... He's earned it.
I might even break the rules and talk to him mid-season on this... With all this drama he's causing and complaining, its not good for the club. He's not happy, and you need your star to be happy. At the VERY least... have the front office call him in, sit him down, and verbally tell him how much he's appreciated and that he WILL be taken care of this winter.