You have to see where Ellsbury is, and with his agent, he wont allow the kid to sign prior to FA anyway. It benefits both parties. Ellsbury has shown an alarming loss of power. Couple that with a shoulder injury that was rehabbed and you have to think that there is something structurally wrong in the shoulder. I wonder if the sox are going to see something on his post-season MRI/physical. But, if the physical goes well, the kid strengthens the shoulder in the offseason and comes back hitting 20+ bombs and running around the bases like a madman again, then you gotta try to keep him.
Also, a huge problem the sox seem to have is letting their guys go and overvaluing their prospects/undervaluing the wrong prospects. With the sox sunk in almost all areas of the team, they might be better served to see what they have next yr, and build for another run. They won in 2004 with veterans, but their 2007 team was grown either via trade of prospects or the ascension of prospects. Right now, their best prospects are in AA and will likely require another half season to be ready. The sox should, IMO, not do anything drastic (ie long term contracts) this offseason (maybe re-sign Ross and coax Papi into a 1 yr deal). They can try to find scrap heap signings for the rotation and hold spots for guys like Barnes, Webster and De la Rosa. Once those kids show they have mastery over AAA, they ascend, take the spots and show if they can handle it. If they show what Doubront has shown (great stuff, inconsistent command, big time promise) then you gotta ride with them. If they come up and look like Craig Hansen, you demote them and deal them before their stock is ruined.