A Contract Extension for Jon Lester?

Chip wonders if the Red Sox should extend Jon Lester now,

'Jon Lester' photo (c) 2011, Keith Allison - license: http://creativecommons.org/licenses/by-sa/2.0/Rob Bradford of WEEI asked a very interesting question on Tuesday, and it’s certainly one worth examining.  Here’s what he had to say:

“If Lester hadn’t signed his five-year, $30 million extension (with a $13 million club option for ’14) in the spring of ’09, he would have been hitting the free agent market this season. (As a quick aside, if the lefty finishes in the top two of Cy Young voting his ’14 option disappears.)

And while ’12 represented a dramatic turn for the worse, with Lester finishing at 9-14 with a 4.82 ERA in 33 starts, he’d still represent a highly valued pitcher given his age (28), health (good), and pre-2012 track record. From 2006-11, Lester totaled the fourth-most wins of any lefty in baseball (76), while managing the sixth-best ERA (3.53) and batting average against (.245). The Red Sox were also a gaudy 98-57 over that stretch with Lester on the mound.


Simply put, even with the downturn of ’12, Lester was going to put a dent in somebody’s payroll if that extension hadn’t been signed. And, whether or not you view the southpaw as a top-of-the-rotation pitcher, if he does leave, that’s another significant hole for the Red Sox to fill.

So, with history as a guide, the question should be asked: Might it be time for the Red Sox to approach Lester once again?”

At first glance, this might sound like a crazy proposition.  Jon Lester is coming off of a disastrous season in terms of traditional stats.  His win-loss record? 9-14.  His ERA?  A bloated 4.82, by far the worst of his career when adjusted for the run environment.  Strikeouts?  After dominating hitters with a 9.4 K/9 mark over the course of his three previous seasons, his rate plummeted to 7.3.  Home runs?  He allowed quite a few of those with 25 round-trippers.

Advanced statistics have painted a much rosier picture for Lester’s 2012 campaign.  His .312 batting average on balls in play indicate that he may have been a touch unlucky.  The same is true for his career worst 13.9% HR/FB ratio.   In theory, over enough innings both of these indicators will regress toward the mean.  This explains why his FIP and xFIP were 4.11 and 3.82 respectively.

While there’s a certain degree of legitimacy to the luck argument, it’s very difficult to contribute everything to bad fortune given what we all saw.  Poor control and poor location, played a much bigger role.  Lester often put himself in hitters counts, which forced him into one of two situations:  either he nibbled and walked too many batters or he threw strikes that caught too much of the plate and got hammered.  Regardless of the outcome, the additional baserunners he allowed caused more runs to cross the plate.  It turned into a vicious cycle.

Luckily, Lester’s track record suggests he’s an ace (or a near ace) quality pitcher.  As a pitcher entering his age-29 season, it’s fair to expect him to bounce back to his at least the 2011 version, if not the 2010 version.  If he does rebound as expected, his contract situation becomes a little more interesting.

Currently, Lester is under contract through the end of the 2013 season.  The club holds a very reasonable option for 2014 that would pay him either $13M if it was exercised or $250K if it was bought out.  Either way, it’s a win-win for the Red Sox.  If they want to retain him, they’ll have a very good pitcher on their staff who will likely be underpaid considering the on-field value he’s producing.  If they decline his option, the cost to the bottom line is negligible.  As such, they’re under no obligation to negotiate an extension with him right now when they have the added cushion of a very club-friendly option year as a buffer.

Still, might it be better to try to sign him for 2014 and beyond? 

Honestly, it’s not a bad idea to explore.  Why?  For starters, we’ve already established Lester’s pedigree as a top of the rotation pitcher.  Those types of pitchers are neither plentiful nor cheap.  Even if he hasn’t turned into exactly the pitcher we’d hoped he’d be, he’s still pretty damn awesome.  That, in of itself, has value.  Secondly, Lester is coming off of the worst full season of his career.  His value is at his lowest.  The amount of money he could reasonably demand in any contract negotiation is considerably lower than it would have been after the 2010 or 2011 seasons.  As a result, the Red Sox could be able to sign him at a bargain price…relatively speaking.

Of course, Lester has to be interested in negotiating a contract extension now.  The club option on his current contract for 2014 is very reasonable.  Despite the incredibly low cost of the buyout, it’s likely to get picked up regardless of his performance in 2013.  Furthermore, the franchise has been in flux for the past fourteen months.  This may give him reason to pause.  As such, he may be content riding out 2013 in hopes of not only rebuilding is value, but also getting a better feel for the direction of the Red Sox.  At the very least, it could put him in a much better position to negotiate during the 2013 offseason.  Then again, he could see the option for 2014 looming, and choose to enter negotiations now in hopes of retaining the feeling of security brought on by a long-term deal.

What should the Red Sox do?

I’m in favor of the Red Sox negotiating a new contract extension, provided the terms are reasonable.  The cost for premium starting pitching is skyrocketing both via the free agent and trade markets.  We aren’t just talking about ace-quality starters either.  We’re talking about middle-of-the-rotation guys as well.  As a result, it’s becoming increasingly more important to retain the talent you already have in house…assuming you have it.  Lester definitely qualifies. 

In terms of a contract, there are a few things I’d like to see happen.  First of all, I’d like to see the 2014 option declined.  The option is only for $13M, and the buyout is dirt cheap.  It’s probably better to fold that season into his new contract.   

Secondly, I’d like to see the contract extension limited to three years.  Once Lester’s current deal expires, he’ll be 30.  It doesn’t take a genius to understand that baseball players typically decline once they hit that age.  Lester has a lot of wear-and-tear on his left arm due to the number of innings he’s thrown.  Naturally, he’ll become more susceptible to injury the longer he continues to pitch.  Additionally, limiting his contract to only three seasons not only improves long-term payroll flexibility, but also lowers the overall risk of the contract. 

Lastly, I’d like to see the average annual salary of the contract settle around $17-18M, if at all possible.  While this might sound like a lot of money (and it is), it’s actually slightly below market value for a pitcher of his caliber.  Considering he’d under contract, as opposed to being on the free agent market, this might be doable.

Overall, Lester has been too good to not at least consider the option of extending him.  If Lester’s camp starts requesting parameters that are far outside of what the Red Sox are comfortable accepting, they should step away from the table.  With one, potentially two, season(s) remaining, no one should be in any rush to get a deal completed.  Still, completing one now could end up saving the Red Sox a ton of money if Lester rebounds in a big way in 2013. 

What are your thoughts on a potential Jon Lester extension?  Is it a good idea?  Will three years $54M get it done?  Is it too much money?  Not enough?  You tell me.  Share your thoughts in the comments section below.

Categories: Boston Red Sox Jon Lester

After being slapped with a restraining order for stealing Nick Cafardo's mail, I was forced into retirement for a brief period of time. As fun as it was to lounge around the community pool and play shuffleboard with noted internet columnist, Murray Chass, I quickly felt a yearning to write again. Now in my second tenure with Fire Brand, I have set lofty goals of achieving world domination, ending the plight of the hipsters, and becoming BFFs with Mike Trout. I am fluent in two languages (Sarcasm and English, in that order); have an intimate relationship with M&Ms; firmly believe that Lucille is the best character on Arrested Development; and spend my spare time trolling select members of the Boston media. You can follow me on Twitter @Chip_Buck.

3 Responses to “A Contract Extension for Jon Lester?” Subscribe

  1. Daniel Poarch October 26, 2012 at 6:23 PM #

    I say do it. I don't think he'll be this bad ever again. That's just a gut feeling, though.

  2. Steve October 30, 2012 at 10:22 AM #

    Go ahead and offer but I doubt he signs. Not in his best interest to sell low if he thinks this year was an aberration.

  3. Gerry October 31, 2012 at 4:15 PM #

    I would hope they offer Becket/Lackey money in a 5/1 deal keeping him through 2018. Of any pitcher in the system, including Doubront, Morales, DLR, Webster, Barnes, Renaudo, Pimental, Workman, etc., Jon Lester has the best chance in that time frame to be the Ace or near-ace. He is sufficiently valuable, as his history demonstrates, to take such a flyer on. For that matter, that premier status applies to Sanchez, Jackson and others that we hope Ben signs.