Lust for the Lackeyluster (or: How I Learned to Start Worrying, and Hate the Deal)

If you're a Red Sox fan, it's hard not to like Theo Epstein. Sure, maybe not all his deals pan out, but how critical can you be of the man who led the Sox to two World Series titles. For Theophiles, there's a tendency to look at every deal as a brilliant coup. Which is why I'm looking at the Lackey deal, and the proposed trades that might result from it, very closely.

Signing Lackey is an exciting move - he's the best free agent starter on the market, and getting him makes our rotation more intimidating for 2010. And yet, I HATE this deal.

Let's be clear about this: Lackey is good, not great. His career FIP is 3.83; by comparison, Beckett's is 3.61, Sabathia's is 3.59, and Halladay's is 3.47. A more comparable player is A. J. Burnett, whose FIP is also 3.83, although Burnett is a better strikeout pitcher (career 8.37 K / 9, vs. Lackey's 7.2 K / 9). For this, we would commit over $16 million a year to Lackey, for five years, making him the highest-paid player on the team (until Beckett gets extended).

Furthermore, there are strong indications that Lackey won't provide much value over the course of his contract. Matthew Carruth at Fangraphs lists two big reasons to be concerned about Lackey: health (Lackey only averaged 170 innings the past two years) and declining stats (higher walk rates, fewer K's). I'm not terribly distressed by his health, but more walks and fewer Ks are very worrisome, especially when Lackey wasn't the best strikeout pitcher to begin with. Lackey may be worth his $16 million in years 1 and 2 of the deal, but years 3, 4 and 5 could be quite ugly.

I think this move is more about hurting the Yankees and Angels. Lackey made great sense for the Yanks, who need another starter to join Pettitte. The Angels suffer even more, especially now that Halladay and Lee are both off the market. However, beyond 2010 both teams can recover, especially by dipping into the next free agent pool (which has Webb). So for one year of pain for the LAA of A and NYY, the Sox are taking on an expensive, declining free agent. [Click Continue Reading for why this deal doesn't fit Theo's M.O., and possible trade implications.]

Generally, Theo stays away from inking the best free agent on the market (exception: shortstops). If the Red Sox do sign a top-flight free agent, he's either a shortstop or an underrated player (see Drew, J.D.). But a player like Lackey is not underrated or undervalued, and he doesn't come at any discount. Over Theo's tenure, the Sox have been building their rotations around players they traded for (Beckett, Schilling) or developed (Lester, Buchholz). This strategy has been both cost-effective and successful, and the few times we've departed from it (see Matt Clement) haven't produced results.

Because Lackey's signing was elective (like plastic surgery, which he needs, btw), there's rampant speculation that a Buchholz trade may be in the works.  Signing Lackey fills the #3 starter role, and allows Clay to be moved with others for a player like Adrian Gonzalez or Miguel Cabrera. Both of those players are great hitters, and a blockbuster trade is probably the only way to get either of them.

And then what? The Sox have to extend AGon (think $18 million + per year) to keep him past 2011, or pay Cabrera's gargantuan salary. Between Lackey and Cabrera / AGon you've got nearly $40 million in two players. By contrast, Buchholz + Adrian Beltre is unlikely to cost more than $20 million, even assuming big arb raises for Buchholz. That means more money to keep players like Josh Beckett, Victor Martinez, Ellsbury, Papelbon, Bard, etc. The Sox could also have passed on Lackey and saved money to sign upcoming free agents like Webb, Mauer, Pujols, etc. Without a major expansion of Red Sox payroll, the Lackey signing and a big trade could severely restrict the team's options in the future.

Buchholz may never be as good as Lackey, but he will be cheaper. I would argue that Buchholz has a small chance of being much better than Lackey, of becoming an elite pitcher like Halladay or Schilling. With all the trades we turned down to keep him (especially the Johan Santana deal), it seems crazy to send him packing now.

The Lackey signing is unnecessary, wasteful and could conceivably hurt the team down the road. Much like the Scutaro deal, it seems directly at odds with Theo's long-term, farm-centered strategy. I don't like it, and neither should you.

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