What's this about Dempster having a drinking problem? He belongs in the bullpen, anyways. Was Cubs closer for several years. He certainly didn't belong pitching against NY the 3rd game of that series.
The braintrust on the Red Sox (if you want to call it that) has to stop thinking about the future, because the future is now. For example, they should have recognized their weakness against LHP much sooner, as was pretty obvious, and done something about it. Instead, they sat on their heels and let the Yankees get Soriano and Reynolds. Is Gomes better than Soriano? Not against LHP. In this situation, you think 2 months--not next year. And then there's the obvious platoon situation at SS, with Drew hitting around .200 against LHP. Bogaerts waiting in the wings... and waiting.
When it comes to aggressiveness and timing, Cashman runs rings around Cherington, who probably needs five alarm clocks to wake up in the morning.