Ryan Dempster is old (turns 36 in May), struggled in the AL last year, and has an astonishingly meiocre career record of 124-124. So is he worth signing? He would add depth to the Red Sox rotation, but would also add salary. Perhaps too much salary. And in his one foray into AL baseball, with Texas last season, he struggled.
The Red Sox are reportedly in talks with him. But Dempster is the type of guy who you add to a rotation that is already good at the top. He's a guy that completes an already good rotation, not a guy who turns around a bad rotation.
The top of the Red Sox rotation is not good. It's got more question marks than The Riddler's wardrobe. Dempster is a decent pitcher, but the price he seems to be commanding on the open market is too high.
The Red Sox are like a fishing boat with plenty of bait, but few fish biting. They shouldn't waste their bait to get medium-sized fish. They should save it for the big ones that will be available in the years to come.