Signing Jon Lester to Long-Term Extension Is a No-Brainer for Red Sox

Zachary D. Rymer@zachrymerMLB Lead WriterJanuary 24, 2014

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The Boston Red Sox can get away with not signing Jon Lester to an extension. They'll have options if he walks, something he could very well do after the 2014 season.

But since Lester is apparently willing to make like Dustin Pedroia and give the Red Sox a discount on a long-term deal, then, hey, why the heck not? As averse to long-term deals as Ben Cherington's Red Sox seem to be, they should know a good deal when they see one.

We'll get to breaking down why soon enough. But first, we need some context.

At an awards dinner this week, Lester acknowledged to Peter Abraham of the Boston Globe and others that he's well aware that Clayton Kershaw just got $215 million and Masahiro Tanaka just got $155 million, but he knows signing an extension would mean signing for less than market value.

Said the 30-year-old southpaw:

I understand to stay here, you’re not going to get a free agent deal. You’re not going to do it. It’s not possible. You’re bidding against one team. I understand you’re going to take a discount to stay.

Do I want to do that? Absolutely. But just like [the Red Sox] want it to be fair for them, I want it to be fair for me and my family. If we can get to something in spring training, that would be awesome.

Lester added: “I want to win. If that means taking a Pedroia deal [a modest $110 million over eight years] where you stay here for less money to be happy and be competitive and win every year, let’s do it. Let’s get it done.”

Now, Cherington must know that he has a wealth of MLB-ready or near-MLB-ready arms waiting in the wings. One of those is Henry Owens, a lefty B/R's Mike Rosenbaum has down as Boston's No. 2 prospect between Jackie Bradley Jr. and Xander Bogaerts. If he's the real deal, he'd be more than a fine replacement for Lester.

Another thing Cherington has to know is that next winter's market could be loaded with talented pitchers. Max Scherzer, James Shields, Homer Bailey and Justin Masterson are all slated to be free agents. If the Red Sox don't extend Lester, they could use their riches on somebody else next offseason.

However, we can all see how the cost of good pitching is skyrocketing. It's not likely to slow down next winter considering how much talent will be out there. So if the Red Sox sign Lester to a discounted extension now, it's probably going to look like even more of a discount later.

That's one reason extending him is a no-brainer. Beyond that, it comes down to what Lester has been in the past and what he is now. And after what happened in the second half of 2013, the latter is just as encouraging as the former.

Let's briefly talk about Lester's track record, which is quite strong. Since he came into his own in 2008, he's compiled a 120 ERA+ over 1,232.0 innings. Per, the only other lefties who can say that are Cole Hamels, CC Sabathia and Cliff Lee.

Look strictly between 2008 and 2010, and you'll see that Lester and Sabathia shared the top of the lefty charts with 17.6 rWAR apiece.  So for a while there, Lester had a strong claim to the title of baseball's best lefty. A high honor, indeed.

What's more, Lester's also been durable. He's been on the disabled list just once since battling cancer in 2006 and 2007, and it was a mere 15-day DL stint with a shoulder strain in 2011. Aside from that, his arm and shoulder have been fine.

That's Lester's track record. In short, pretty good stuff. Yet another reason for the Red Sox to feel comfortable about extending him.

David J. Phillip/Associated Press

Then there's what Lester did following the break last season. You'll recall he was outstanding, posting a 2.29 ERA and a 3.43 K/BB across 122.1 innings in 18 starts between the regular season and postseason, and he was able to do it because he wasn't pitching like he had been ever since late 2011.

You might remember that span. In 70 starts from the end of 2011 to the All-Star break of 2013, Lester posted a 4.46 ERA and a 2.44 K/BB ratio over a little under 440 innings. It was a rough stretch, one that made it easy to ponder, "You know, maybe this guy just doesn't have it anymore."

What led Lester out of it? Mainly a much-improved four-seam fastball that he allowed himself to trust a whole lot more.

It's encouraging enough that Lester isn't bleeding velocity. His velocity did peak in 2009, but Brooks Baseball can show that his velocity has actually been staying steady rather than declining.

Even more encouraging is that Lester's velocity was on the upswing when we last saw him, as was his effectiveness. Here's some more numberific data from Brooks Baseball:

Jon Lester's Four-Seamer
SplitUsage %VeloBAAISO
9/11/11-ASB 201338.6692.71.278.211
Post-ASB 201349.3593.29.239.137
Brooks Baseball

That's not the biggest velocity spike you're ever going to come across. But in a sport where mere microseconds can make a big difference, a pitcher adding over half a mile per hour to his heater can likewise make a big difference. 

And in this case, that it happened was no fluke.

Here's where I'll concede the floor to FanGraphs' Eno Sarris. After Lester had done his (quite big) part in helping the Red Sox win the World Series, Sarris investigated all the talk that had gone on about Lester's mechanics and found some interesting things.

What Sarris noticed was a subtle change that took place with Lester's delivery in the second half, one that involved him being a bit more direct to the plate with more drive from his back leg. This helped lead to the increased velocity, which in turn led to increased trust in it and better results with it.

It was at Boston manager John Farrell's encouragement that Lester went about fixing his mechanics. As such, the notion that Farrell, Boston's pitching coach from 2007 to 2010, would be able to help get Lester back on track in his first year as manager ended up being validated. 

That's a comforting notion for Cherington regarding Lester's extension candidacy, as it means that potentially keeping Lester around would mean keeping him paired with a guy who can keep his mechanics and, thus, his stuff in working order.

Of course, we would be remiss if we didn't note the other big change Lester made in the second half of the season. It involved him being considerably less predictable with one pitch in particular: his cutter.

Lester's cutter used to be his go-to pitch with two strikes. So much so that it got to a point where it really wasn't much of a two-strike weapon.

But then this happened:

Jon Lester's Cutter with Two Strikes
SplitUsage %VeloHMov (in)BAAISO
9/11/11-ASB 201336.0089.821.84.235.150
Post-ASB 201326.7289.
Brooks Baseball

You can see in the velocity and horizontal movement that Lester's cutter didn't really get nastier. But simply by cutting down on his use of it with two strikes, he was playing against the book on him. With hitters more on their toes, it's no wonder his cutter produced better results when he did use it.

Now then, let's clarify why all this kinda-sorta complicated stuff is important.

I'm guessing the Red Sox are receptive enough to keeping Lester around based solely on his track record and his clean injury history, not to mention his relative youth and left-handedness. But they must also want some assurances that the pitcher they got in the second half of 2013 is the pitcher they're going to get going forward.

No such assurances would exist if Lester's strong second half was the product of mere luck. That's been known to happen with pitchers, and the way in which luck tends to manifest itself in a given pitcher's ERA can lead to misleading conclusions about said pitcher's talent (see Kelly, Joe for an example).

But Lester's second half wasn't the product of luck. It was the product of adjustments, ones that encapsulated the best of both worlds: They made him both a better thrower and a better pitcher. The result was the triumphant return of a pitcher who had been one of the game's best lefties in the very recent past.

Again, the Red Sox don't have to extend Lester. They'll have options if they don't. But when you have a chance to lock up a lefty starter who's both proven and looking good for the future at a cheap price, well, sometimes you just gotta do it.


Note: Stats courtesy of unless otherwise noted/linked.


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