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But can he play in October?

It looks like the answer to that question is yes for at least 2 players (as in, Ellsbury and Buchholz). That is, my understanding of other people's understanding is that the Sox could add any two players who were anywhere in the organization at midnight on 8/31 to the playoff roster. I say two players because Brenden Donnelly and Matt Clement are on the DL. If someone else is added to the DL (the 15-Day or 60-Day) as we enter the post-season, that would be another spot that can be filled by anyone in the organization.

Apparently there used to be a position-for-position rule that is not gone. That is, prior to this year, if you put and outfielder on the DL, you could only replace him with an outfielder, but you could replace him with any outfielder in the organization. The other interesting change is that if someone is injured mid-playoff series, he can be replaced mid-series. He would then be done for the remainder of that and all of the next series. But, that's a great, fair rule.

I garnered most of this info from a great post by Amalie Benjamin on the Globe's blog. She quotes extensively Brian O'Halloran, the Sox director of baseball operations. This is what he says about the mid-series injury situation:
...teams now are allowed to substitute for an injured player during a series. Such in-series substitutions are position-player-for-position-player / pitcher-for-pitcher, and the injured player cannot be active for the remainder of that series or the next series. Those substitutions also require MLB approval.

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