Jon Lester extension: Red Sox should be patient with negotiations

Scott Rovak-USA TODAY Sports

Jon Lester is likely in line for an extension at some point soon, but the Red Sox would be wise to wait a bit.

There is this thought around the game of baseball that, in order for a team to succeed, they need an ace at the head of their starting rotation. While that has been largely disproven, it still seems to be true that they at least need good, front-line starters. On their way to the 2013 World Series title, the Red Sox found one of those guys in the middle of the year in Jon Lester, who performed admirably down the stretch of the regular season, then pushed forward to another level with an amazing postseason. Unfortunately for Boston, the soon-to-be 30-year-old left hander will be entering the final season of a six year deal signed prior to the 2009 season. Because of his performance at the end of the season, he could be looking at some big money if he hits the open market, especially considering the contracts that have been thrown around already this winter.

For this reason, the Red Sox will do what they can to lock him up with an extension. While the discussions likely won’t begin until Spring Training as to not mess with the 2014 team’s luxury tax, it would be smarter to wait even longer than that. There are still plenty of question marks surrounding Lester, and while it could be risky to wait, they should wait a few months into the regular season before deciding whether or not they should work out an extension.

We’ll start by looking at why Lester is such a hot commodity right now. Even beyond how well he pitched, he’s a homegrown talent, drafted all the way back in 2002. There’s a connection between him and the city, especially after he was diagnosed with non-Hodgkin Lymphoma in 2006, eventually returning from the illness and helping the team to the 2007 World Series. He has stayed connected with the community throughout his tenure in Boston. Then, of course, there is his tremendous skills. He’s been a workhorse in his career, topping 200 innings in five of the last six seasons, tossing 191-2/3 frames in the one other season. During the team’s improbable playoff run this season, Lester started five contests, going 4-1 with a 1.56 ERA over 34-2/3 innings, a legendary stretch. Even in the final two months of the season he was outstanding, with a 2.78 ERA over 74-1/3 innings, with a 58/20 K/BB ratio. Clearly, he has the stuff to be outstanding in this league. However, is that the Jon Lester he’s going to be going forward?

Photo Courtesy of Gail Oskin

It wasn’t so long ago when people weren’t sure if Lester was even a middle-of-the-rotation pitcher anymore. It was easy to throw his awful September of 2011 away due to small sample sizes, but he followed that up with an extremely rough 2012. Though he was able to avoid injury once again, he struggled to a 4.78 ERA and an 87 ERA+, the first (and only) below-average ERA+ of his career. That year, he also saw his strikeout rate fall to 19 percent, after K-rates of 23, 26 and 27 percent in the last three years, respectively. He struggled for a large portion of the middle of this past season as well. From May 20 to August 2 - a span of 14 starts - he pitched to a 5.81 ERA while batters hit .304/.367/.504 off Lester. Of course, these are arbitrary endpoints and should be taken with a grain of salt, but they do show that for a large portion of the season, he was extremely hittable.

There are plenty of reasons to believe that 2012, and that middle chunk of the 2013 season were an aberration for Lester. If that turns out to be the case, the Red Sox would be taking a huge risk by not trying to get an extension done as soon as possible. The more he pitches well, and the closer he gets to the open market, the more it’d cost to lock him up long term before that can happen. There’s a very real possibility that the Red Sox would be costing themselves a huge amount of money by waiting a little longer to try and figure out who Jon Lester actually is.

Even considering the risk, though, waiting on an extension until the summer of 2014 is the best move for the Red Sox, all things considered. While it’ll give them time to see what they have in Lester, it also gives them time to see what they have in their young pitchers. There is a possible scenario - however unlikely it is - that Allen Webster, Anthony Ranaudo, Brandon Workman and Matt Barnes all prove to be worthy of a starting gig in 2015. At that point, paying huge dollars for Lester doesn’t become as vital for the team. There’s also the fact that the Red Sox aren’t the Athletics. Efficiency is the name of the game in today’s MLB, and avoiding albatross contracts is key. However, if they end up waiting too long and Lester plays himself into an even bigger deal, Boston can afford to pay him what he earns. It wouldn’t be an ideal situation, but this franchise can still pay big money for a certain caliber of player, especially a homegrown potential ace.

There will be a lot of talk in the coming months about locking up Jon Lester. After what he did in this past postseason, many think he is a sure-fire front of the rotation pitcher. It doesn’t seem so simple, though, as he’s had plenty of recent struggles as well. Between getting a better look at some of the young arms, and being able to endure a potentially higher price tag, the Red Sox can afford to wait a few months on Jon Lester.

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