Every team wants good players. That's how you win baseball games. Jon Lester is, I think it's easy to agree, a good player. So his current team, the Boston Red Sox, should want to keep him. Lester himself has said he wants to stay with Boston. So this should be easy. [Pours coffee.] [Waits for article to write itself.]
But, of course, it's not that simple. [Drat.] If it were, this would be an article about how the Red Sox re-signed Jon Lester. But it's not. One of the reasons is, at least on a macro level, the two sides have stopped negotiating. Lester's old deal is up at the conclusion of the current season, so the time to give him a new deal without letting him test the market is dwindling. Oddly, it seems the Red Sox are content to let that happen.
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There has long been a debate in Boston. Is Jon Lester an ace? That word is just a label and whether it fits Lester depends on how you define "ace," not Lester. We know what Jon Lester is.
Lester is a 30 year-old left-handed starting pitcher, who was drafted out of high school. He was supposed to be traded to the Rangers with Manny Ramirez in the aborted deal for Alex Rodriguez. Thanks to the players union, Lester stayed with Boston. In 2006, he reached the major leagues and got diagnosed with non-Hodgkin's lymphoma. After receiving effective treatment, Lester returned to the Red Sox in late July of 2007, and eventually started the fourth and clinching game of the World Series in the fall. He also started and won two games of the 2013 World Series.
In between there have been great seasons ('08 and '09 were both six win seasons by Baseball-Reference's WAR) and less great seasons (2011 and a particularly rough 2012 season), but overall Lester has been quite valuable. Since 2008 when he began starting regularly, he's been worth an average of four wins a season. That is very good. What is perhaps better is that, since 2008, he's averaged over 200 innings per season and is one of 19 pitchers to throw 1,200 innings (and only one of five left-handers to do it).
Since 2007, the year he became a semi-regular starter, Lester is 12th in pitcher WAR. He's well behind Justin Verlander, Felix Hernandez and Cliff Lee, but ahead of Adam Wainwright, James Shields and Tim Lincecum in total value. Over those eight seasons, Lester has been roughly equal in value to Matt Cain and Wainwright.
It may be relevant, then, that the Giants gave Matt Cain, 29, a six-year, $127.5 million contract extension two seasons ago, and the Cardinals gave Wainwright, 32 five years, $97.5 million last year. Both Cain and Wainwright were a year from free agency at the time of their deals and though both were at different ages when they signed, the average annual value of their deals is similar.
It has been reported that Lester (who's having an excellent season so far: 2.75 ERA, 10.7 strikeouts per nine innings) was offered a four-year, $70 million extension, a smaller $17.5 million AAV over fewer seasons than either Wainwright, Cain, or any other comparable pitchers who have signed free agent contracts or extensions.
He's younger and has been healthier than Wainwright, but his numbers aren't quite as good (the level of competition might mitigate this difference at least somewhat). He's older than Cain but his peripheral numbers are better. Which brings us back to whether Jon Lester is or isn't an ace.
Here are three complicating issues to said status.
1. Downward trend in performance. Lester has been a very valuable pitcher throughout his career as I hope I've demonstrated above, but it is also true that his two worst full seasons have been his last two full seasons. When you look at the way Lester's career has gone, the direction does not look promising.
That's a chart of Jon Lester's three WAR numbers by the three main purveyors of WAR (Baseball Prospectus, FanGraphs, and Baseball Reference). They're all slightly different, but they all show that Lester was amazing back in 2008 and 2009 and has been increasingly less so since. The caveat to that is that this season Lester has been more valuable already than he was in all of 2012 by two of the measurements.
2. Age. Lester will be 31 next season, the first after signing his next contract. You don't have to think too hard to name pitchers who haven't performed well in their 30s. Take CC Sabathia. (Seriously. The Yankees would like you to take him.) Sabathia is 33 and in the midst of an expensive long-term contract. He's also in the midst of a second consecutive bad season, made worse now that he's hit the disabled list with a knee issue and is about to see the dreaded Dr. James Andrews. For every Cliff Lee (who has maintained a steady level of performance at age 35), there are usually two Johan Santanas or Josh Becketts.
3. Young pitchers in the system. While most teams would dread losing a pitcher of Lester's caliber, the Red Sox are in a fairly advantageous position when it comes to young pitching. They've got a stacked rotation in Triple-A featuring first round picks Anthony Ranaudo and Matt Barnes, hard throwing former Dodgers Rubby De La Rosa and Allen Webster, and last year's World Series set-up man Brandon Workman. In Double-A they have likely top prospect Henry Owens, who almost threw a no-hitter last week. There are arms deeper in the system as well, like last year's seventh overall pick Trey Ball. The system is stacked with pitching talent. How many of those guys are going to turn into players that can replicate the success of Jon Lester? That's the question the organization has to answer because each of those players will, if they make the majors, earn about one fortieth of what Lester will make next season. While that's nice, if they're worth a fortieth of Lester's performance on the field, the Red Sox won't win many games.
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As it stands now, Lester brings top-of-the-rotation upside, while staying mostly healthy. These are valuable commodities. While you can't project health without huge error bars, the biggest indicator of future injuries is past injuries and for a starting pitcher with over 1,400 big league innings on his arm, Lester's injury history is remarkably short. So the Red Sox are left with a tough call: Commit big money to a pitcher entering his 30s, or watch a star walk away, quite possibly to a rival. More fun: Amateur GMs will judge the Red Sox decision for years, no matter what the team does. So, prepare yourself for one of the following headlines in 2019:
* Lester Beats Sox Again As Wait To Jump Off Tobin Bridge Reaches Weeks
* Yankees Mercenary Lester Loses Again; "$25 Million for this?" ask Fans
* Another Series Win Puts Franchise Icon Lester In Rare Company
* Red Sox Forced to Let Bogaerts Walk as Lester's Contract Repeatedly Beats Franchise About The Face With Dead Fish
It's the kind of decision that can make your head spin. Is Lester an ace? Is he this good? Will he stay healthy? The Red Sox don't and won't know the answers, but they'll have to make a huge bet one way or the other. Don't envy them.