A freak injury resulted in a lost 2010 season for Jacoby Ellsbury. To go along with the injury he left the team to rehab in Arizona which only ruined his image even more in the eyes of Red Sox fans. 2011 has been a different story for the former first round pick. Ellsbury has enjoyed a resurgence in 2011 as he has hit for a solid .296 average and compiled 15 stolen bases to go with his 22RBIs. Many fans expected the Sox to let go of Ellsbury after his last year of arbitration in 2012 but maybe fans should start to reconsider.
The main reason I think the Sox should extend Ellsbury is because he is proven. Despite the bad 2010 season, he was a solid player in 2008 and 2009, and looks to be doing even better in 2011. Carl Crawford is prof that no matter how great a player the replacement may be there still is a chance he won't be better then the incumbent. John Lackey is another example of a free agent signing bust. Now, although the Sox are looking to maybe replace Ellsbury with one of their younger prospects like Ryan Kalish or Josh Reddick (depending on which guy plays right for Drew), neither of these players are quite proven enough either. I think the sox should let the 2 prospects battle for J.D Drew's spot while definitely holding on to Ellsbury. By the time Bryce Brentz and Kolbrin Vitek are ready for the majors( 3 or 4 years from now), The Red Sox will have a better look at how to approach their outfield situation.
My Verdict: Extend Ellsbury to a 4 year deal worth 36 million ( 2 years of the deal will cover the remaining arbitration years).