Getting Ryan Dempster, one of a handful of mid-rotation starters who now represent the best pitching options on the free-agent market, for just a two-year deal is a small coup for the Red Sox. Other starters in this group, such as Kyle Lohse and Anibal Sanchez, apparently want deals of four or five years, and Dempster is very close to them in quality and risk, close enough that for his deal to be half that length is a big win for Boston.
Dempster's success in Chicago the past few years was largely the result of his stuff, not just of facing some very weak competition, and he should be able to maintain most of his production after moving to the AL East. Dempster still has two above-average off-speed pitches in a mid-80s slider that he throws for strikes (and throws quite often) and a low-80s splitter that functions like a hard changeup with some late tumble to keep hitters from elevating it. He does need to keep his fastball out of the middle of the plate, especially moving to the AL East, and I worry somewhat about any pitcher who has relied as heavily on a slider as he has.
He carries the same risk as any experienced starter in his 30s, and I'm sure some anxious Red Sox fans are flashing back to Matt Clement, another former Cubs starter who was broken the day he walked in the door and whose three-year deal with the Red Sox was a total loss. But this market really pointed to a three-year deal for someone like Dempster, so getting him for two years is good value and limits the downside risk for the club.
Youkilis a good fit for Yankees
The Yankees signed Kevin Youkilis to a one-year, $12 million deal in an obvious fit for both sides, maybe more so for the Bombers since there was no other palatable third-base option available. Youkilis came up as a third baseman but spent most of his earlier career at first, shifting back to third on a regular basis in 2011 and playing roughly average defense there over the past two seasons.
Even if he's five runs below average with his glove for New York, he's better than any other alternatives available to the Yankees, and provides some modest on-base skills and right-handed pop to make himself an average player overall. He gets to play in a decent hitters' park for a year to try to hit the market again next winter, and New York gets some production out of third base while giving A-Rod a full year to try to get rid of this hip issue for good.
The only significant negative for the Yanks is that Youkilis isn't as durable as he once was, playing 122 games or fewer in three straight years, but the market wasn't coughing up any better 150-game options.