Note: This article was inspired by several things. One was some original research done by the author weeks ago. Two was this Sons of Sam Horn thread, and three was this article by Ben Badler from Baseball America where he actually did the research I had intended to do. Credit where credit is due.
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The Red Sox have not had what you might call success when it comes to free agency. To prove the point we don't need to run through a whole bunch of numbers, though we can if you enjoy getting physically sick, but for these purposes a simple list of names will suffice.
Those five players cost the Red Sox a shade under $60 million in 2011. But the common thread between them is not that they were expensive, the Red Sox could afford that. No, the commonality is that they were awful. Putrid in some cases, but achieving full fledged awfulness in all.
In fairness, Jenks was awful then hurt. And it probably isn't completely fair to call Drew's contract awful though his season certainly was. The point sustains no damage to say the Red Sox spent $60 million, more than the Tampa Rays payroll, on effectively nothing at all. Just threw it right into the rubbish bin.
The five names above isn't the extent of the list either. There is a precedent going back through Theo Epstein's time in Boston. Look back at the 2007 World Champion Red Sox roster. The best free agent on that team was Manny Ramirez, but he was signed by the previous administration (in fact it was common knowledge that Epstein attempted to get rid of him numerous times). After that, could the best free agent on the team really be Julio Lugo? Fortunately not, because '07 was Drew's first year in Boston and no matter what you think of Drew, he was unquestionably better than Lugo. On the pitching front you had Daiusuke Matsuzaka and Julian Tavarez. Not inspiring stuff.
It's all enough to raise the question, are the Red Sox just bad at big ticket free agency? While there is ample evidence to give an affirmative answer, I think it may be premature. Recall, teams make free agency choices without the benefit of hindsight. In other words, they can only use the information that existed at the time. I's unfair for us to look at the way specific deals turned out and then criticize the team after the fact for things they could not have known at the time.
So the question becomes, was it reasonable at the time they were signed to think the contracts doled out to the above five players would end badly? (To be clear, I know labeling the Crawford contract a failure is premature after one season, but as it was a season that went so utterly terrible I think it's fair to include it here for now.)
Let's take a look at those five and see if there is some pattern or a discernible potential for failure.
1. John Lackey - In the four years before signing with Boston, Lackey's walk rates consistently rose while his strike out rate consistently fell. Also, after five years of throwing at least 198 innings, Lackey experienced an injury which held him to 163 innings pitched the year before signing with the Red Sox. Then there was his age. The Red Sox would be paying for Lackey's age 31 through 35 seasons. Not one of those factors is a death knell by itself, but putting them all together paints a picture of a pitcher in decline. That's not to say it was fated or even obvious that Lackey's contract would turn into the burden it has become, but there was at least some reason to question the deal the day it was signed.
2. Carl Crawford - Crawford is the anti-Lackey in that there seems to be no statistical warning of impending doom. His numbers were mostly trending upwards and age was on his side before coming to Boston. If there were no or few reasons to question Crawford the player, there were reasons to wonder about Crawford's fit with the Red Sox. Taking Crawford out of the Rays lineup where he was a premium offensive player compared to his team mates and putting him into Boston's where he wasn't could allow pitchers to pitch him more aggressively, resulting in fewer walks. Of course if he adjusted to that he'd reap a higher batting average and possibly a higher slugging percentage as well.
It is also true that fewer walks aren't terrible for a player with as many different avenues to accumulate value on a baseball field. It's unclear how the Red Sox or any team for that matter could have predicted that Crawford would turn in a performance even half as bad as the one he actually turned in. The only way one might have been able to see this coming is by focusing on what Joe Sheehan calls soft factors (maybe others call them that too, but that's where I first heard it from). Soft factors are non-quantifiable aspects, like chemistry, fit, and the like. If the Red Sox had refused to sign Crawford even though he was a premium player at a position of need because the left field wall at Fenway Park wasn't perfect for him, or because his game is more suited to turf than grass (a thought belied by his splits), that might be a reason to fire the GM.
3. Bobby Jenks - A victim of a high BABIP last season, Jenks came to Boston ready to assume the 8th inning or, if Papelbon pitched like he had the previous two seasons, possibly the ninth. Instead he pitched 15 innings all season, giving up 12 runs in the process. As a reliever, and a very large one with crumbs in his beard, it isn't hard to see Jenks as a risk. He's a walking, talking, doughnut-eating risk. Jenks and conditioning go together like Andy Dick and the Catholic Church, so there was reason to worry. He just turned 30, though that isn't an outrageous age by any means.
4. JD Drew - Drew's five year contract consisted of two excellent seasons, possibly the best by a free agent outfielder ever in Boston, two decent seasons, and then the disaster that was 2011 where Drew slugged .302. Drew experienced some personal problems at the beginning of his tenure in Boston that may have impacted his performance, though in his defense the team won the World Series so it couldn't have gotten in the way that much. Drew's contract covered his age 31 through 35 seasons, so some decline was expected. It's an open question whether or not the Red Sox would re-do the contract again if they could go back in time, but as DeLoreans are expensive to acquire I don't imagine they'll be doing that anyway making the question moot.
5. Mike Cameron - Cameron was old when they signed him, though the two year deal wasn't going to debilitate the team even if it turned out atrociously, which is good, because it did. Cameron was immediately severely injured and never was able to regain any semblance of his former self. In the team's defense, it was a freak injury, but one that considering the player's age and position, the team should have and likely was prepared for when they signed Cameron.
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By my count, roughly three of the five were questionable at the time. Lackey because of decline issues, Cameron because of age, and Jenks because he is a large man who stores candy in his beard. I'm utterly befuddled by Crawford and I don't think I'm the only one. Drew's contract is a polarizing one, but one that was fairly successful until this season. In a better universe the Sox would have wrung a bit more value out of Drew.
Finally, while these weren't necessarily fatally flawed signings from the beginning, they were risks and part of taking risks is accepting losing. The Sox seem to have received the brunt of that big stick to the side of their head recently and repeatedly so. Still, anytime you bet on a player for four years, or five, or even seven, there is a large component of luck involved. Each player is an individual and even though statistical trends may tell you one thing, and it may be corroborated by the historical record, that best educated guess may not come to be.
It's unfair to paint eight years of Theo Epstein's rule as General Manager with a brush consisting of just five free agents. In no way is this article intended to be any kind of statement about whether or not Epstein should return next season. I firmly believe he should, though looking at his recent free agent signings, Epstein may be right when he said the organization needs to revamp it's decision making processes in regards to signing free agents.