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Depends on whether Colletti thinks he can re-sign Dempster or not. As to him being stupid, he's seemed to be quite shrewd with trading... and not trading in the past. I doubt the FO will take big advantage of him. Then again, we don't know how highly he values his current prospects... nor Dempster. If we end up getting back a haul we'd deem more valuable than we expected... I think we may get a problem child that Colletti knows something about, and is wise enough to not broadcast.
There have been some makeup issues with Gould. I wonder if that is why his name has been leaked a few times.