There are many who preferred Edwin Jackson as a Red Sox target over Ryan Dempster, but there was a method to Boston's madness in acquiring the elder right-hander. The pitching market had not completely set itself then, as what had signed was mostly pitchers with question marks like Brandon McCarthy, and the very top of the crop in Zack Greinke. When McCarthy, who has made all of 43 starts in the last two years combined -- and just 60 in the last four -- thanks to recurring shoulder issues, is pulling in two guaranteed years and over $15 million in guaranteed money, you know the market could become problematic fast.
So, the Red Sox jumped in on Dempster for two years at just over $13 million a piece, with Boston accepting that average-or-better had a price range in this lucrative market, but Dempster conceding, at his age, that he was only going to get two years despite the impending rush on starting pitching. While the deal looked solid in a vacuum, what Edwin Jackson ended up pulling in would be one of those things linked to Dempster's contract, as he's produced similarly in many ways, and still has youth on his side given he won't even be 30 until the end of next season.
You won't have to wait long to see if the Red Sox were fleeced or not, as Jackson has pushed his demands up to four years, eliminating all suitors from his market besides the Cubs, who missed out on Anibal Sanchez a week ago, and the Texas Rangers, who are currently wondering why no one wants their substantial money to be their own.
According to MLB.com's T.R. Sullivan, the Rangers are willing to go as high as four years and $50 million for Jackson, or $12.5 million per year. The money isn't outrageous -- it's a little less than what Dempster is pulling in on a per year basis -- but four years for a pitcher who has been so thoroughly average is a little off-putting, youth or no.
You can blame the Sanchez deal for this, as he, who is a good, not great hurler, pulled in five years for $80 million from the Tigers. It's no surprise to see a pitcher a step down on the chart from Sanchez get the kind of offers Jackson is, but that doesn't necessarily make it the right fit for everyone. Dempster fits better into Boston's short-term plans, as they're awaiting the development of their pitching prospects, and focusing on winning with the core that's in place for much of the next two seasons in the meantime. This, while avoiding sacrifices that could damage the future of what general manager Ben Cherington likes to refer to as the "next great Red Sox team."
Jackson, as an average pitcher, is useful, for sure. But at four years, you run risks, both financially and in terms of roster space, when discussing pitchers. He's only been above-average by ERA+ in one of the last three years, and crossed the 200-inning threshold the same number of times in that stretch. He has nearly 1,300 innings of mileage on his arm, and while he's been durable to this point, guessing at exactly how a pitcher's elbow and shoulder are going to react with even more innings and aging is a difficult business -- there's inherent risk in every pitcher, whether they've been injured previously or not. Some pitchers are just riskier than others, and while Jackson has been in the less-risky camp, the more years you tack on, the more likely it is that something could go awry on your tab. With an elite pitcher, that risk is worth it. With someone like Jackson, that's debatable. Dempster has even more mileage on his arm, and is older, but that's why he just got the two years.
Jackson is not bad, but he's not necessarily someone you go out of your way to get, either -- hence his being on five different teams in the last four years, and on the way to his sixth in five. Boston was able to secure a similar pitcher in terms of production in Dempster, for less total money, two fewer years, and just slightly more per season. With the way they're setting up their future, that's the right move to make, in the same way eschewing Sanchez for Dempster was.