At the end of this season, Ben Cherrington is going to have a lot on his plate as he is going to have to deal with some of his own free agents. One of the big free agents the Red Sox will have will be Jacoby Ellsbury.
The market for center fielders this offseason looks very slim and Jacoby Ellsbury will be looking for a huge payday. There appears to be mutual interest between the Red Sox and Ellsbury to discuss a new contract this winter, but how much will the Red Sox pay for Ellsbury's services?
Scott Boras is Jacoby Ellsbury's agent and he has a history of making players filthy rich. I'm sure Boras will be playing hardball with the Red Sox to make Ellsbury a rich man. Since there will not be a huge market in free agent center fielders, this could potentially boost Ellsbury's stock value and make teams pay a lot to obtain him.
If Ellsbury had played well every season like he did back in 2011, I could definitely see why he would be worth over $100 million. He had a .321 average with 32 homers, 39 stolen bases, 105 runs batted in and a league-leading 364 total bases.
Unfortunately for both Ellsbury and Boras, the injury history for Ellsbury and his age are going to determine what contract he will get this winter from teams. Ellsbury is now thirty years old and I would be very hesitant to pay a 30+ year old $100 million for a long period of time. Ellsbury has also missed a lot of time in 2010, 2012 and parts of this season because of various injuries, so that's another reason why I wouldn't dig deep into my pockets to retain him. Injury prone.
I like Jacoby Ellsbury and I have enjoyed watching him over the years here with the Red Sox. If the asking price is going to be too high, I would say let another team pay that much. Bottom line is I do hope that Ellsbury remains here with the Red Sox, but worst case scenario would be that we will just have to be patient with Jackie Bradley Jr. and let him become the next great center fielder in the future in Boston.
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