The Brandon Five
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When the Sox signed Crawford to that absurd contract, I openly wondered why since they already had a Crawford on the team by way of Jacoby Ellsbury. From what I've read and heard over the years, Ellsbury is the type of player that wants to play out his years till free agency. His having Boras as an agent lends credence to that. Obviously the Sox have a history of locking up players before they hit free agency, but those guys (pedroia, lester, youk) are different animals than Ells is. Lester had cancer, and the latter 2 of high intensity dirt dog guys who love playing in Fenway. Not to say that Ellsbury doesn't like Fenway, but he comes across as more of a delicate soul so to speak. Of the group, he seems like the most likely to seek the largest deal. When he sees Crawford sign for $142 million to play LF, he's got to wonder what he's worth in CF. He's going to be looking for $20 million per I'd think, or $15 million per at a minimum. I don't think the Sox would pay that to two identical OF'ers. They'd probably prefer to invest that in a power bat, corner OF type. You can only have so many $10-20+ million players on your roster. In 2013 I think the higher dollars start to kick in on the other 3 who signed early too. It will be interesting to see how it plays out. I'd imagine that the Sox might even consider trading high on Ellsbury this offseason, if they know a long term deal will be difficult. With 2 years of control left they'd get a serious haul I'd think.
A base-stealing, home-run hitting, high BA center fielder with above average range is worth at least $15 million. You would need two players to replace that kind of production.