Long-Term Lester

As I wrote back in October, it can be difficult for a player to shake a reputation. Fortunately, for the Red Sox, Jon Lester accomplished this very feat by showing everyone that he was a legitimate ace pitcher and not merely a cancer survivor with raw tools and potential. The 25-yr old lefty, who tossed a no-hitter in the 2008 season, put together a tremendous statline in 33 starts en route to +5.1 wins. Production like that translated to $23 mil at fair market value. Still well under club control, Lester of course earned nowhere near that salary.

His production did not go unrewarded for long, however, as he has just signed a 5-yr extension worth $30 mil, with a 6th year option valued at $13 mil. The extension buys out all of his arbitration-eligible seasons as well as his first two free agent years, and has the potential to keep the southpaw in Red Sox attire until he turns 31 years old.

Lester is tough to project thanks to just 144.1 innings logged in 2006-07 and the fact that the systems do not tend to recognize or reward breakout performances. The projection systems housed here suggest that Lester will take a decently sized step backwards, regressing to somewhere in the +3.5 to +4.1 win range. I’m a tad more optimistic and see him potentially as a +4.5 win pitcher if he can match the innings pitched total from last season.

Normally, with extensions, we break out the 40/60/80 calculator and determine the worth, but what intrigues me about this particular extension is that it has become hard to determine the true “winner” of deals this offseason. With the market as depressed as it has become, a deal that seemingly possesses a slam dunk pedigree such as this might be a bit more fair than meets the eye. Either way, the Red Sox have done a solid job of locking up two of their best players in Lester and Pedroia, players who will no-doubtedly outearn their salaries.

With the inconsistencies of Daisuke Matsuzaka, the potential that we have seen the best days of Josh Beckett, the question marks surrounding John Smoltz, Clay Buchholz, and Brad Penny, and increasing odds that Tim Wakefield will retire one of these years, the Red Sox have just locked up their best pitcher, ensuring themselves of an ace for the next several years. And if the aforementioned inconsistencies, question marks, and odds prove to be irrelevent with 2009 performance and beyond, Lester has the chance to headline one of the top rotations in the game for years to come.