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Jon Lester isn't worth it for the Yankees

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For the second straight winter the Yankees are going to try and spend their way back into the postseason. Jon Lester shouldn't be their answer.

Lisa Blumenfeld

For all their woes on offense, the Yankees are going to spend a lot of time over the next few months worrying about their pitching. The number of starters they have under contract and free from injury concern heading into 2015 amounts to a grand total of zero. As well as their scotch tape rotation has performed this year, it doesn't provide much in the way of long-term certainty. Brandon McCarthy and Hiroki Kuroda are free agents to be, Ivan Nova and CC Sabathia are on the mend from major surgeries and Masahiro Tanaka's right UCL gets so much press it should have its own publicist. Shane Greene's breakout rookie season has come on the back of a spotty minor league track record, David Phelps has had arm troubles of his own and Michael Pineda hasn't exactly demonstrated he can be counted on.

So yes, it's pretty much a given that the Yankees will be on the hunt for starting pitching, especially since the coming free agent class looks much stronger there than it does on the position player side. The name that's speculated most often belongs to Jon Lester. At 30, he's in the midst of arguably the finest season of his career, currently sporting a 2.54 ERA, 2.76 FIP and 1.10 WHIP, all of which are personal bests. His success hasn't been luck-based. His BABIP, left-on-base rate, and homer-to-fly-ball ratio are all right around his career norms. Lester has plenty of experience pitching in the American League East and in the postseason, and he's been pretty extraordinary in the latter, where he boasts a 2.11 ERA and 1.04 WHIP in 76 2/3 innings. Lefties historically spend less time watching their pitches sail over the short right-field porch at hitter-friendly Yankee Stadium, and since Lester was dealt at the trade deadline this year, he's ineligible for a qualifying offer and won't cost the team who signs him a first round pick like fellow free agents Max Scherzer and James Shields most certainly will. Then there's the whole "stick it to the Red Sox" philosophy of roster construction, which has guided Yankee off-seasons for the past ninety-plus years and has brought plenty of Boston expatriates to the Bronx. For all those reasons, Lester will be tempting - maybe too tempting to pass up.

Wait a minute...this is supposed an article about why the Yankees shouldn't go all-in for Lester. Obviously there are some pretty strong points to be made for the opposite point of view, that is, until you think seriously about what a free agent Jon Lester is going to cost. There's a very strong chance that when the dust settles on this winter's free agent frenzy, Lester and Scherzer will emerge in some order as the second and third highest paid pitchers in baseball history. Lester is very, very good, but giving him a contract worth something close to, or north of the seven-year, $180 million pact that Justin Verlander is currently nursing would be severely stretching the boundaries of what sort of pitcher gets paid that kind of coin.

Over the past seven years, eight pitchers have signed deals for six or more seasons, worth $135 million or more. Here's a look at their performance in their three seasons prior to landing those commitments, compared with Lester and Scherzer who will soon expand the roster to ten.

Pitcher Contract FIP FIP- fWAR
Clayton Kershaw 7 years, $210 million (2014-2020) 2.58 70 18.6
Justin Verlander 7 years, $180 million (2013-2019) 2.97 70 20.3
Felix Hernandez 7 years, $175 million (2013-2019) 3.00 78 16.1
CC Sabathia (Part I) 7 years, $161 million (2009-2015) 3.10 71 19.4
Masahiro Tanaka 7 years, $155 million (2014-2020) N/A N/A N/A
Zack Greinke 6 years, $147 million (2013-2018) 3.16 78 13.3
Cole Hamels 6 years, $144 million (2013-2018) 3.34 85 12.5
Johan Santana 6 years, $137.5 million (2008-2013) 3.21 74 19.3
Jon Lester ??? 3.51 85 12.9
Max Scherzer ??? 2.93 72 15.9

This isn't a referendum on how these guys have performed once their deals were signed, but rather what they did that made their value so high. The only pitcher on the list with numbers comparable to Lester's is Hamels, but his deal began before his age 29 season, whereas Lester will throw the first pitch of his next contract at 31. I wouldn't have much of an issue handing Lester the Hamels contract, but that's not very realistic since he's going to end up with at least $25 million more than that guaranteed. While Lester's uncharacteristically poor 2012 skews his numbers downward, his 2014 performance is uncharacteristic, too. Going back five years instead of three doesn't improve the picture much. In that span, Lester's FIP drops only by 0.02. If the Yankees are insistent on spending copious sums of cash on a front line starter this winter - and there's a good chance they will be - Scherzer seems like the better bet, even with the draft pick cost attached.

It's not that Lester isn't phenomenal...he is. Barring catastrophe, 2014 will be his seventh straight season making 30 starts or more. His reputation for reliability and his postseason pedigree have earned him Andy Pettitte comparisons, and those are actually pretty fair. Pettitte's 3.74 career FIP and 84 FIP- are right in line with Lester's marks of 3.59 and 83. But Pettitte was never among the highest earning players on his own team, let alone in baseball. He was paid like good number two or three for the most part, never working on a contract longer than four years or for a salary higher than $16.4 million. Like Pettitte, Lester hasn't usually been someone who's dominant enough to out-pitch bad hitting. No matter what the Yankees offer him, it will be hard for him to have a significant impact if the team spends another year as an offensive bottom-feeder.

The Yankees have a decision to make on how they'll approach the rotation this winter. They can pull the old dump truck full of cash routine on Lester or Scherzer, or they can spread the wealth around by re-signing McCarthy and Kuroda for about a third of the total cost, combined, while hoping for the best from Tanaka and Pineda. It's not like option "A" isn't alluring. These are the Yankees and they can pay guys what they want without feeling much of a pinch. But there is a limit somewhere. No matter where it is, not allocating twenty-something million per season to a starter would leave them more to work with toward improving a lineup that badly needs help.