The Cubs and Athletics just pulled off a doozy, swapping a handful of top pitchers for a handful of top prospects. Should the Red Sox follow suit?

Jon Lester by Kelly O’Connor of sittingstill.smugmug.com

Sure, say that prospects are over valued, or what ever you might like about the issues with the trade itself, but it has its merits. The Red Sox face a similar, if not identical problem as the Cubs faced just weeks ago. John Lackey is the Red Sox’ Jason Hammel and Jon Lester, their Jeff Samardzija. It’s obviously far from a perfect comparison, but is it possible to swing a similar deal?

Addison Russell‘s dont exactly grow on trees, but it’s not out of the question to wonder if Boston’s pitchers could fetch a similar return.

Jon Lester is almost a sure bet to depart at the end of the season and as such comes with less control than Samardzija and thus a smaller return. Ignoring records, the two have pitched relatively similarly, Lester to a 2.92 ERA and a Samardzija to 2.83 in a comparable number of innings pitched.  They have also managed a nearly identical WAR, with only .1 win separating the two pitchers.

Lackey and Hammel meanwhile are a different story.  Hammel, this season has by far been the superior pitcher, not to mention the four year difference in age. Hammel has amassed 3.1 WAR while Lackey has only managed 1.3 thus far. That said, Lackey owns nearly three times the career WAR that Hammel does. Hammel is in the midst of a career season, while Lackey has been a work horse for his entire career, excepting the Tommy John injury.

I don’t want to name names, as prospects of Russell’s caliber are few and far between. I think it would be unreasonable to expect a return of a Russell-type, Billy McKinney and Dan Straily. That said, I think a top-100 prospect might be a possibility, especially if acquired by a desperate team much closer to the trade deadline.

As I said, the length on Lester’s deal will no doubt drive his price down since teams will be less inclined to part with top prospects for rental pieces. But Lackey is a potentially attractive piece thanks to the reduced rate he comes at for next season. Unfortunately, there were some rumblings on the twitter-sphere that Lackey may instead choose to forego the minimum salary and retire at seasons end instead of make only ~$500,000.

The Red Sox have significantly less leverage than the Cubs held with Billy Beane and the Athletics. Lester is one year older and is a free agent at seasons’ end and Lackey is older than Hammel and even though he is under contract for next season, whether he plays or not could be up in the air. That, combined with Lackey’s poor performance in comparison to Hammel, means the Red Sox are in for a significantly lower return than three top prospects from a single organization.

The Red Sox likewise do not have to trade Lester or Lackey, either in a package or separately.  Ben Cherington and Co. must decide whether whatever he can acquire for Lester is worth more than the compensatory draft pick they would receive assuming Lester declines a qualifying offer. Given Lackey’s status for next season, teams could decide to pay a premium for a two-time world series champion who will make only the league minimum next year.

Teams tend to overvalue prospects, a weakness which Billy Beane exploited on Friday. Boston should take advantage of that overvaluation in an effort to generate a larger return than they might garner from a compensatory draft pick. History shows (Cliff Lee and C.C. Sabathia come to mind) that teams will way over-pay for quality pitching in the last year of deals. The Red Sox ought to wave the white flag on a lost season and take as much as they can get for their assets.