Let's keep in mind that the Sox had a big management shakeup in the offseason and a conflict about whether the new GM should pick the manager. Plus Henry turned off the money. It was a difficult situation for the FO, but Cherington exascerbated the problem by trading for a closer (Bailey) instead of a starter (Gio G.) because he had a bug up his ass wanting to start Bard. That has blown up in his face on two counts. He also had another bug about Iglesias and Lav needing more "experience". I think he was wrong there, too. Too bad V didn't have more of a say on the matter, but that was Henry/Lucchino's fault.
As for Jackie whatnot, that was a dagger effort designed to get her promoted--maybe. Youks did not get a fair shake there. His opinions are probably shared by a few other players. It's a good argument for keeping women out of the clubhouse.