Dempster – flickr’s EmmyMik

The Red Sox and Ryan Dempster are reportedly in serious discussions on a contract, Ken Rosenthal reports. While the Red Sox do need a pitcher capable of pitching in the middle of the rotation, staring at Dempster’s 5.09 ERA in 12 starts with the Rangers is certainly sobering. Add in the fact he’s likely to receive three years as a 35 year old (26 on May 3) after turning down two-year offers from (at least) the Red Sox and Brewers, and suddenly you have to question the wisdom of such a deal.

But there’s a lot to like about Dempster. For example, even with that 5.09 ERA, he finished the year with a 3.38 ERA, marking the fourth time in five years his ERA has been under 4. Over that five year span, he’s thrown 997 1/3 innings of 3.74 ERA ball, punching out 911 and walking just 361. As Fire Brand’s own Hunter Golden pointed out on Wednesday, Dempster does well at limiting walks, and Boston seems to be going after hurlers who can do just that. Walks have been a problem for the staff recently, and Dempster’s 2.71 BB/9 in 2012 certainly shows that he limits walks.

Pete Abraham of the Boston Globe is less than impressed with the idea of Dempster, though, pointing out his 5.68 ERA in September. But as tends to be the case when you’re talking small sample size, ERA is not a good indicator of success. If you strip out all his luck-based figures and look at his actual production, Dempster posted a 3.76 xFIP in September. In fact, all season long, the highest xFIP Dempster posted in one month was June, when he ad a 4.15 mark. It’s the only time all year he was north of 4.00, so that 5.09 Rangers ERA should be taken with a healthy dose of salt.

The always-valuable RedSoxStats Twitter account illustrates as much, pointing out “Ryan Dempster’s main issue with Texas was luck, .330 BABIP, 66% LOB%. Actually had excellent peripherals (SwStr%, GB%, K/BB).”

And Mike Axisa tweets: “170+ IP and 7.7+ K/9 in each of the last five years: Lincecum, Felix, Hamels, Dempster. That’s it.”

Long story short? Dempster is a good pitcher.

What makes me nervous, though, is that he will turn 36 in May, meaning he’ll be well into age 39 by the time a three-year contract expires. Can pitchers reasonably be expected to hold up over three years at those ages? Ever since Dempster returned to the rotation for the Cubs in 2008, he’s been extremely durable, although he did miss some time in 2012 with a right thigh strain and right shoulder strain. He hasn’t had any prior history with shoulder injuries, so there’s nothing to be particularly worried about there, except if you think he’s getting more brittle with age, and that’s something that shouldn’t be discounted. In addition,  his fastball velocity has been dropping consistently for three years. Last year, he averaged 89.7 mph with his fastball, down from 90.3 the year before, which was also down from 91 the year before that. Prior to that, he had been pitching comfortably in the 91-92 mph range.

Perhaps as an answer to his velocity issues, he’s reinvented himself as a pitcher, relying heavily on a split-fingered fastball he incorporated in 2009 that allows for separation from the fastball, even as the fastball velocity ticks down. He’s also added a cutter to his 2012 repertoire, and while Fangraphs believes his cutter was ineffective, there’s some indication that it helped play his fastball up. But what really concerns me is Dempster’s reliance on a slider, which has been his best and most-used secondary offering his entire career. There’s a link between heavy slider usage and injuries to the arm, and that’s where Dempster’s shoulder strain this past year might shoot up a red flag.

When compared to other pitchers on the market, I’m not sure giving Dempster three years is a smart thing. I would much rather the Sox take a flier on another pitcher that has some risk attached to him, such as Shaun Marcum or even Brandon McCarthy, who signed a two-year, $15.5 million deal with the Diamondbacks. (I have no idea if McCarthy would have even wanted to go to the east coast, but I sure hope Boston at least kicked the tires.) That’s where upside comes into play. Heck, the team should certainly look into Anibal Sanchez although he’s thought to be looking for six years around $90 million. He’s actually a remarkably similar pitcher to Dempster (h/t @RedSoxStats) but there’s less risk attached to Sanchez. What Dempster offers isn’t upside and risk. All he offers is who he is, plus risk attached to potential injury and age. (It should be mentioned that the Sox are trying to maximize flexibility with the roster, and by the time that third year rolls around with Dempster, in theory, the team’s young cadre of pitching prospects can hide any regression from Dempster. That flexibility goes away with Sanchez, but then again, there remains plenty of flexibility with the rest of the rotation.)

In the end, this deal is going to come down to the team’s evaluation of Dempster, just like its evaluation of Shane Victorino and Mike Napoli will also determine the likelihood of these deals working out. Victorino will only work out if his bat speed returns. Napoli works out if he’s not completely brittle and can sustain his power. These three deals are a major referendum on the evaluation skills of Ben Cherington and Co. There’s already been a bit of discontent against Cherington for his (so far) failed deal with the Athletics in trading Josh Reddick for Andrew Bailey and (perceived) failure in trading Jed Lowrie-plus for Mark Melancon, although I’m not part of the latter camp. I am all for maintaining flexibility, but the only way these significant dollars to aging free agents that don’t seem to have upside attached to them work out is if their evaluation skills are spot on. In that sense, I’m far more interested to see how these deals work out from a front-office perspective, not so much on the field.