Though the working relationship between Jon Lester and the Red Sox organization remains civil and complimentary, there seems to be a growing split between the two parties regarding Lester's value as a starting pitcher. Though the Red Sox are rumored to have offered a deal in the $70 million range on a four-year stint, the response from the Lester camp was cool, to say the least.
And though the Red Sox have made a concerted effort over the past few seasons to be more fiscally responsible, they do still clearly sit in the upper echelon of franchises in regards to revenue, sitting comfortably behind the Yankees and Dodgers while still looking down on a majority of the Midwest teams and their southern counterparts.
But all of this back and forth between one side and the other has never really gotten down to the central question of whether or not Jon Lester is actually worth the $70 million offer he presumably received, or even worth the presumably much higher amount that he (or, at least his agent) seem to think that he is worth.
Jon Lester has been a remarkably durable pitcher over his career, making at least thirty-one starts since his sophomore season, bottoming out at 191.2 innings in 2011 and topping out at 213.1 innings last year. From 2008 to 2013, he averaged 4.48 fWAR per 200 innings, putting him solidly in the upper tier of starting pitchers over that same time frame. The only pitchers to accrue more Wins Above Replacement over that same stretch is a short, distinguished list; Cliff Lee, Justin Verlander, CC Sabathia, Roy Halladay, Zack Greinke, and Clayton Kershaw.
And therein lies part of the problem. For the first three years of this stretch, Lester averaged just over 5.5 WAR. Over the last three seasons, though, Lester has averaged just 3.67 WAR. He also turned 30 prior to the season, meaning his well on his way to the declining phase of his career, where injuries and a loss of youthful vigor have a tendency to rob a pitcher's effectiveness.
Complicating things further is the fact that Lester is on his way to having potentially the best year of his career. His strikeout rate has spiked to 10.23 K/9 (career 8.20) in addition to limiting his walks and keeping the home run in check.
So let's assume he ends this season around 5.5 WAR, a reasonable figure considering his past performance. Pitchers who have earned around 14-16 WAR over the previous four seasons are some household names, to say the least: Zack Greinke, Doug Fister, Roy Halladay, Adam Wainwright, C.J. Wilson, James Shields, Mat Latos, Gio Gonzalez, and Hiroki Kuroda.
Zack Greinke received six years and $147 million prior to the 2013 season, though he had the best pitching season in recent memory on his resume at the time. C.J. Wilson received five years and $77.5 million from the Angels after posting 9.7 WAR over two years with the Rangers.Hiroki Kuroda has more or less been averaging about $18 million a season during his tenure, though he is pushing 40.
The most recent trend outside of Chavez Ravine has been to show more caution regarding long-term investments in starting pitchers. Anibal Sanchez, coming off of a career year in 2013, re-signed with Detroit for $80 million over five years. And though Lester is perhaps a touch better than Sanchez, Anibal also signed his deal heading into his age-30 season.
If the rumors are true, and the Red Sox offered four years and $70 million, that would seem to be about in-line with recent trends regarding starting pitcher contracts.. Lester could almost certainly find a team somewhere willing to go an extra year for a few dollars more, but the negotiations seem to be in the ballpark of standard operating procedure around the league. And though effective free agent spending is paying a player for what he can produce over the length of his contract, too often players are paid for recent performance instead of future projection. And the truth is, Lester has been one of the top ten pitchers for over half a decade, and those guys don't come cheap anymore, even if he hasn't been what he once was.