I've always been against spending significant money trying to upgrade the middle or bottom of the rotation, so it really was nothing personal against Dempster. At least I never called him one of the worst pitchers in the league, like I did Masterson.
I get why they signed Dempster, and I get what he brought to the clubhouse, but I was against the deal when it happened, and then his production on the field was much worse than his previous seasons before coming to Boston. I guess that soured me even more.
It wasn't just Dempster and Masterson, it was Penny, Smoltz, Colon, Wade Miller, Paul Byrd, Jake Peavy, Erik Bedard and Aaron Cook. At least I've been consistent.
I realize some of these guys were in season acquisitions needed to fill a gap during a playoff run. Sometimes, there wasn't many other options, so I couldn't and didn't blame the GM for getting some, but I just hate the idea of building a staff from anywhere other than the top (or at least a solid 3 type).
I always viewed Brentz as Middy-light. I must have suggested hundreds of Middy trades--back when he had value. 25% K rate and unsustainable/diminishing power. I never rooted against Brentz or any Sox player, but I just never had any high hopes for the guy.