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What is Jon Lester really worth? And are the Red Sox better off waiting him out?

Posted by David D'Onofrio  February 26, 2014 11:17 PM

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The widespread assumption, given the apparent desire on both sides to make it happen, and maybe even more so given the freshly magical memories of this past October, is that Jon Lester's next contract will come from the Red Sox. Possibly soon, but whether it's in the coming days, coming weeks, or even coming months, most seem to anticipate an agreement will be announced, and the only question is the number dollars and years that'll comprise the terms of the deal.

The lefty himself has promulgated the idea by saying at various times that he wanted to stay, by suggesting that he'd be willing to take a discount to do so, and by recently reiterating that he'd be open to beginning negotiations. As a good union man he's also said he doesn't want to set the market back, but upon hearing that re-signing their staff ace could seemingly be done without a fight, the prevailing belief among Sox fans and followers seems to be that there's no sense letting it get to the point he could leave. The logic says that if Lester is so open to an extension that he would forego free agency, then get it done. Give him five or six years. Give him $100 million. Heck, give him $120 million. Do it. Now.

Or wait -- and potentially save tens of millions of dollars, while maybe also even mitigating the risk of regretting the late years of the deal half a decade from now.

A case can be made that Lester warrants a nine-figure contract. Clayton Kershaw and Homer Bailey both got one this winter, and in doing so became the fifth and sixth hurlers who've signed extensions so large since the middle of the 2012 season. Topped by Kershaw's $215 million whopper, the average haul on those agreements has been roughly $158 million.

But that doesn't depict the entire financial landscape a starting pitcher nowadays encounters as he seeks his next big payday. And it's the rest of the picture that challenges the assumption that the Sox should (and would) be eager to pay Lester big money before they need to do so -- based simply on comparisons of Lester to those who've been paid handsomely for a long-term extension, and comparisons of the southpaw to those who have been forced to find their money as free agents.

Here are those comparisons, for your consideration. First, the six pitchers who've agreed to extensions worth at least $100 million since the start of the 2012 season (click on the chart to enlarge it):


Between Kershaw and Lester, there really is no comparison -- nor is there a comparison between Kershaw and any contemporary pitcher at this point, really. Verlander's career numbers are hampered somewhat by his more inconsistent early days, but a better sense of his performance might be reflected in theCy Young votes he's received in six different seasons (compared to Lester's one). Lester's numbers compare more favorably with Cain's, though it's worth noting that when the Giants signed him to his extension he was in the midst of his third sub-3 ERA season in four years, he'd yet to allow an earned run in three postseason starts, and, most importantly, he was almost two and a half years younger than Lester is now.

When the Mariners tacked on five years and $135.5 million to Hernandez's deal before the 2013 season, the prized righty was 26 years old and had posted a 2.85 ERA over the previous four seasons. Hamels is another that Lester's camp could point to, but, again, age is an important consideration -- as it is with Bailey, too.

The Reds righty is the clear outlier in this group, and it remains to be seen if Cincinnati was wise to invest so much capital in a pitcher who hasn't exactly lived up to his perceived potential. But it can be justified by the fact he's two and a half years younger than Lester, with more than 400 fewer professional innings on his arm, and he's on an upward trajectory. The past two years he's basically been as good (or better) than Cain, and per year he'll be paid only $17.5 million. That's not absurd; in fact, if Lester would take a deal paying him $17.5 million annually, the Sox would happily shake his hand and draw up the papers.

Another way to compare the pitchers is to look at the Fielding Independent Pitching (FIP) number of each, and thanks to Fangraphs we can do that via the chart below. You'll notice that when he was 26, Lester was right there with the best of the best. At ages 27, 28, and 29, however, he has -- while still better than the baseball-wide average -- been worse than any of the $100 million men who've reached those respective ages. If that signifies a trend, it's not a favorable one for Boston's ace.

Source: FanGraphs -- Clayton Kershaw, Matt Cain, Felix Hernandez

Now, though, let's look at the starting pitchers who have taken their talent to free agency over the past two winters, and see how they compare to Lester. Figuring that he wouldn't probably settle for anything less -- barring a horrific 2014, or an injury -- we'll limit our look to pitchers who have received contracts of four years or more.

Somewhat surprisingly, there's only seven of those, with Ervin Santana still dangling on the open market hoping some suitor will soon bite. Here's how Lester stacks up against those who've been paid after getting to free agency:


And here's how his numbers fit in from a FIP perspective:

Source: FanGraphs -- Edwin Jackson, Zack Greinke, Anibal Sanchez

Now, against this cast, Lester looks a bit more appealing. He's clearly better than Jackson, Vargas, and Nolasco, and -- though it's a narrower argument -- he's better than Garza and Jimenez, too. Where FIP showed him trending the wrong way compared to the nine-figure pitchers, among the free agents he's almost every year been somewhere between the middle and top of the pack.

Greinke is the most accomplished of this mix, and accordingly his deal is the outlier of the bunch, both the longest (by a year) and the richest (by a whopping $71 million), so if that's the contract Lester's camp brings with it to the bargaining table then their idea of a hometown discount might well be $140 million. But the fairest comparison of all might be made between Lester and former Double-A teammate Sanchez, who re-signed with the Tigers before the 2013 season despite getting the chance to explore free agency.

Lester is a month older than Sanchez, and three injury-plagued seasons earlier mean Sanchez has thrown 325 fewer big-league innings than Lester. And he got his contract at least a year (maybe two) sooner than Lester will. But, beyond victories, the rest of the career numbers for each hurler are almost identical. So Sanchez's five-year, $88 million pact might be a good starting place for the Sox and Lester.

Another good reference point should be the deal the Cardinals struck with ace Adam Wainwright prior to last season, which kicks in this year -- when Wainwright will turn 33. That agreement will pay him $97.5 million over five years. And even though Wainwright lost 2011 to Tommy John surgery, and was outpitched by Lester in Game 1 of the World Series last October, Wainwright has been one of the three best pitchers in the National League in three of his last four healthy seasons. Lester hasn't been one of the three best pitchers in the American League for even one full season in his career.

So, then, based on comparables, and age, and his body of work, Lester is probably deserving of something in the neighborhood of five years and $85 million-$90 million. That's an average of $17 million-$18 million per year. That's not unreasonable for a team with a payroll like the Red Sox', which will include seven players making at least $12.5 million this season.

In fact, at that number the Sox wouldn't necessarily need Lester to take a discount -- so instead the club could attempt to parlay Lester's willingness to sign into a deal with less of a landmine at the back end. If the Sox can convince Lester to begin the extension immediately, thus overriding the final year of his existing contract, they'd pay him more money than the $13 million they otherwise owe him for 2014, but the club will one year sooner be out from under its commitment to a pitcher who'll then be in his mid-30s.

The other option for the Sox is to play out the season, and see what type of market emerges for Lester. If Max Scherzer doesn't re-up with the Tigers, Lester won't be the best available option, and this past winter suggests a general trepidation about giving megabucks to good-if-not-great pitchers in their 30s, especially one who'd almost certainly also cost a draft pick after being extended a qualifying offer, so Boston could choose to gamble and let the real-world demand directly dictate how much it is willing to spend. It's somewhat odd, and illogical, but the evidence suggests the Sox may pay significantly less by exposing him than they would by essentially bidding against themselves.

It's not a bad way to go for Boston -- except that it only takes one team to swoop in and swipe him from atop your rotation. And when the Yankees are willing to pay Masahiro Tanaka $155 million before he's thrown a pitch in the big leagues, it's hardly beyond the realm of possibility that they'd throw silly money at a left-handed horse who is battle-tested in the AL East and has an impressive postseason pedigree, and who would otherwise be the proven leader of a young staff that projects to soon be loaded with the talented young arms that are on their way.

That'd be a risky way to go if the Sox really do want him to anchor their staff now, and later help steer their future -- but, then again, there's risk to signing him early, too, financially in particular. Actually, they're assuming some risk no matter how they choose to handle this situation.

So maybe we're being a bit presumptuous in assuming that something is imminent.

This blog is not written or edited by or the Boston Globe.
The author is solely responsible for the content.

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About the author

Dave D'Onofrio is a sports journalist who focuses on the Red Sox and Patriots, and also writes's "Off The Field" blog about what Boston's sportsmen do away from the More »

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