Measuring The Real Market Value Of Jon Lester

The Boston Red Sox stand on the cusp of trading Jon Lester. In fact, the time it takes me to write this post on early Wednesday evening, might be enough to time to complete the trade. As a Red Sox fan, I’m heartsick. As a baseball observer, I think the Red Sox are being stupid.



Lester is going to be a free agent in the offseason. Last year, in the aftermath of the World Series win, the team had the chance to re-sign the 30-year-old lefthander. Boston offered 4 years/$70 million.

Jon LesterNow, I realize (more so than most) that this is hardly chump change. It’s not money to sneer at in these economic times, or any economic times. But if you compare it to market value for major league starting pitchers, the offer made by the Red Sox was crazy and Lester would have been insane to take it.

I think the point can best be made by comparing Lester to Los Angeles Dodgers starter Zack Greinke, who was on the market prior to the 2013 season. Greinke got a six-year deal with nearly $160 million—more than twice the total value of the offer made to Lester, and nearly $2.5 million higher on a per-year basis.

Greinke is an apt basis of comparison, because he and Lester have had fairly similar careers. They’re both 30-years-old. A typical year for both has seen their ERA somewhere in the respectable 3s, and to be in the neighborhood of 200 innings. Greinke has taken his ERA into the 2s twice, while Lester has one additional year of clearing the 200 IP threshold.

Both distinctions can be seen as a byproduct of either the leagues or park they pitch in. Greinke was able to get a 2.63 ERA last year with the Dodgers, easily better than Lester’s career-best of 3.25 (though the Boston lefty is on 2.52 this season). But that’s in the DH-less National League and a deep home park in Dodger Stadium. Lester doesn’t have that advantage, but the presence of the DH makes working deeper into games more feasible for an American League starter.

The pro-Greinke side of this argument would point to his Cy Young Award season in 2009, when he was off-the-charts good for the Kansas City Royals, winning 16 games and posting a 2.16 ERA. But while Lester can’t match that, he can bring something that Greinke doesn’t—a demonstrated record of success in October.

Lester won the clinching game of the 2007 World Series. He pitched brilliantly in two wins over the Los Angeles Angels in the 2008 Division Series. Lester was dominant in last year’s playoffs, including twice shutting down the St. Louis Cardinals in the World Series. Even some of his notable postseason losses—Game 7 of the 2008 ALCS coming to mind—were more a case of losing a big-time pitcher’s duel, as opposed to not pitching well at well.

Now it’s not like Greinke has been a failure on the October stage, but nor has he stood out. Over six starts between the Milwaukee Brewers in 2011 and the Dodgers last season, Greinke’s ERA is 4.30 and the worst outing was the most significant start of his career to date, Game 5 of the 2011 NLCS when the Brewers and St. Louis Cardinals were tied two games apiece. Greinke didn’t make it out of the sixth inning and his team lost 7-1.

The point of this though, is not to knock Greinke’s October record—he pitched pretty well in three starts last year. It’s to say that Lester’s record is superior enough—and the successes recent enough—that it counteracts Greinke’s Cy Young Award and makes the two pitchers comparable in terms of market value.

If the Red Sox don’t want to go to six or seven years on a contract, that’s understandable. The track record on deals for pitchers that go past 4-5 years isn’t very good. But the front office can come up with an offer in that five-year window that’s appropriate to Lester’s position in the market—say $100-$110 million over five years.

Boston is coming off an offseason where they let Jacoby Ellsbury walk and take an insane seven-year deal from the New York Yankees. I was fine with that, and fine with them not replacing Ellsbury, choosing instead to see this year as a chance to re-tool and introduce some younger players. I’m also fine with not going to a sixth year on Lester, and if some other team wants to challenge recent history, so be it.

But I’m not fine with letting Jon Lester leave Boston and not even an attempt made at a legitimate offer. This is more than just a good pitcher, and more than someone that we’ve watched come up through the Red Sox system.

More than most, it seems like we’ve watched Jon Lester grow up. We saw him come up in 2006 as a highly touted prospect. We prayed for him when he was diagnosed with lymphoma later that same year. We cheered his courage when he was on the mound to clinch a World Series a year later.

We saw him make the screw-ups of youth when he got hung up in the chicken-and-beer fiasco of September 2011. And we saw him publicly make amends, come back and be a World Series hero one more time.

All of that has value too. Again, it doesn’t mean, the Red Sox have to resign him at any cost, but they should pull out all the stops. It’s time to put a real offer on the table. Five years. $110 million. If someone else pays more, so be it. But if not, the blame for this lies exclusively on the Red Sox front office.