The Ellsbury Predicament

So Jacoby Ellsbury is up for arbitration for the second time in his career. Assuming the Sox don't suddenly extend him, he'll get a boatload of money 'cause he just had a monster year. But, I do believe that at some point this season the Red Sox should sign Ellsbury to an extension in order to avoid the usual inevitability that comes with any Scott Boras client, which for all you idiots out there who are reading this trying to learn the first thing about this part of baseball, that means free agency and letting teams bid against each other until he gets himself, erm, I mean his client top dollar, whether it be with the same team or a different team. Typically with a Boras client, a long term deal before free agency doesn't happen except for a few rare cases. But, I personally am hoping that Ellsbury is one of those rare cases. So, without any further useless rambling, I will propose my plan:

• First off, avoid arbitration. Sign Ellsbury to a 1 year contract, worth somewhere in the area of $7-9M. It's the right amount of money, and probably right around what he'd get in arbitration.
• Then, right around the middle of the year, sit down with Ellsbury and Boras and talk about a long term extension. He could be worth some big money assuming he continues to play at this level or an even higher level, and buying out an arbitration year would be huge for the team.
• Now, Boras is a stubborn piece of shit, so convincing him to negotiate a long term deal pre-free agency will be a pain in the ass. Hopefully Cherington has someone on his staff that has some sort of ability to manipulate/convince boras to negotiate.

So, in my first attempt at being an armchair GM, I suggest a 5 year, $67.5M contract extension. Criticize all you want people, but it is a fair deal. I suggest this based on 1) his level of play from when he played his first full year up until 2011 (I give him a mulligan on 2010, broken ribs blow). 2) I base it on his level of play in 2011, his breakout year, in which he absolutely killed the ball and was a master fielder (unlike the highly paid man to his right in left field...) and fully deserves a hefty raise. And 3) I base it on my prediction for his level of play in the years to come, which, based on the past two factors, I believe will be at an all-star level.

So while it may seem highly unlikely that they do hammer out an extension pre-free agency, I believe that to be a very fair deal if they do manage to sign one.