Part I: “The Devil You Know…”

The Red Sox have been fortunate enough to have an ace or near-ace for the better part of the last two decades.  From Roger Clemens, to Pedro Martinez, to Josh Beckett, to Jon Lester, the Red Sox have not wanted for much when it came to top of the rotation talent.  The latter two are certainly not of the same caliber as Clemens and Pedro, but Clemens and Pedro are literally once in a generation talents, and even that sells them short.  They are two of the greatest pitchers to ever play the game.  Even so, Beckett and Lester did a fantastic job of carrying the mantle.  Neither pitcher was ever considered the best pitcher in baseball in any given year, but each of them made a couple All-Star teams, and both of them have garnered a handful of Cy Young votes over the past 6-7 years.

For the first time in a long time, the Red Sox find themselves without a clear number one starter (the Sox were without a clear number one in 1997 and 2005, but 1998 saw the arrival of Pedro, and 2006 saw the arrival of Lester and Beckett).  The Sox will also find themselves  with a tremendous amount of money to play around with.  Accounting for arbitration raises and the addition of major league minimum salaries prorated for a full season, the Sox payroll projects to be somewhere between $110 million and $118 million; in other words, they have some significant flexibility.  Not only do the Sox not have a clear number one starter, but they don’t really have a number two or, arguably, a number three starter.  They have some interesting, albeit unproven commodities, who could potentially blossom into valuable pieces, but that’s not a smart way to go about building a contending ball club.

With all that in mind, it becomes evident that the Red Sox need to make a major move to shore up the rotation, through either free agency or trade.  Let’s take a look at the best available (and theoretically available) arms:


Jon LesterLester is the proverbial “devil [we] know” in the old adage, “The devil you know beats the devil you don’t.”  The Red Sox are intimately familiar with nearly every facet of Jon Lester’s baseball playing ability.  They, like most of us, know his statistics, his tendencies, his strengths, and his weaknesses.  They also know his makeup: what makes him tick, what motivates him, and what makes him comfortable.  Taking all this into account, re-signing Jon Lester seems to make more sense than any other conceivable option.  His performance is consistently at or near elite, and he’s remarkably durable (especially when one considers his courageous battle with cancer).  Since the start of 2008, he’s pitched less than 200 innings only once, and in that season (2011), he pitched 191.2 innings.  He’s averaged nearly 4 fWAR per season since his debut in 2006, and he pitched in a very limited capacity in 2006 and 2007.  He has a career strikeout rate over 20% and a career walk rate less than 10%.  His HR/FB% is also less than 10%.  He’s done all of this while pitching in one of the American League’s most hitter-friendly ballparks.  He’s a legitimate star, and I think we’ve kind of taken him for granted.  With all that in mind, it seems abundantly clear that the Sox should do almost whatever it takes to bring him back.

However, there are some worrisome historical precedents that are worth examining before making any long-term offer to Lester.  Using the Baseball-Reference Play Index, I did a search for players who accumulated at least 32 rWAR over any nine-year period, between the ages of 21 and 32.  Over nine years and between the ages of 22 and 30, Jon Lester has accumulated 32.6 career rWAR and put up a career ERA+ of 121.  Roy Oswalt, Carlos Zambrano, Brad Radke, and Johan Santana all had similar nine-year stretches of sustained success (Radke was actually slightly less effective by ERA+ than Lester, and Santana was actually a bit better than Lester, in terms of ERA+), and none of them lasted more than 13 years in the big leagues.  In fact, each of them only last twelve seasons, except for Oswalt, who just kind of hung on and was generally terrible in his last season.  Jered Weaver and C.C. Sabathia also had very similar nine-year performance records, and there are signs that they are on the ropes, perhaps even in the twilight of their careers.  Of course, none of this actually has any tangible bearing on Jon Lester.  He’s his own person, and his future need not be dictated by others’ past.  However, the Sox should (and undeniably will) exercise caution when talking contract length with Jon Lester’s people.  A five-year deal with 2-3 good to great seasons and 2-3 acceptable to mediocre seasons is digestible, but anything beyond that…we’re looking at something regrettable.