Tabling Jon Lester extension negotiations is troubling

I'm struggling with how to start this piece. I toyed with the idea of calling it "Matt gets drunk and complains about Jon Lester not getting an extension" but then I thought that would be too crude. Also inaccurate as I'm not drunk. I'll say this though, the day Jon Lester signs with the New York Yankees is the day I will get powerful drunk. And powerful sick. Also I'll probably break some things. Nothing valuable. But based on the recent news, I'm setting some breakable yet cheap items aside, because that day is coming people. That day is coming.

In case you spent the entire first paragraph thinking 'what the heck is he talking about,' the Red Sox and Jon Lester have "amicably" "tabled" their talks on a contract extension for Boston's Opening Day starter. Lester is entering the final season of what has become a six-year, $43 million contract, which he signed back in March of 2009, and barring a change of heart on the part of the team and the player, he will hit the market at the conclusion of this season. He'll be 31 and, pending the outcome of this season, one of the best starting pitchers to hit the free agent market. Probably the second best behind Max Scherzer.

So that's what I'm talking about. I'm talking about Jon Lester leaving the Boston Red Sox. It might be for the Yankees, it might not. But mark my words, if this extension doesn't happen, he's gone. They're not going to sign him after he hits free agency. Dave Cameron of FanGraphs wrote about this in his write-up on Miguel Cabrera's extension. He said, in part,

...elite players who aren’t signed to long term extensions simply do not re-sign with their original clubs when they hit the free agent market. It just doesn’t happen. Over the last five off-seasons, there have been 30 free agent contracts signed with a total value of $50 million or more. Of those 30 free agent contracts, exactly one — Derek Jeter — re-signed with the team that passed on giving him an extension before he got to free agency.

I'm not sure I'd have correctly guessed the severity of the numbers, but that make sense. And for Lester it means, without this extension, good-bye, Boston. So sign him now or not at all seems to be the Red Sox choice. Lester has publicly stated on numerous occasions that he wants to stay with the Red Sox. He wants to spend his whole career in Boston and he's willing to give the team a home-town discount on his contract to do it.

Everything was lined up. And now nothing is happening. Why?

Photo credit: Rob Carr

Well of course I don't know specifically. The team and the player didn't line up on the terms of the deal. It's easy to speculate that the Red Sox are the ones at fault here, because Lester clearly said he'll give the team a discount. Here's the thing though. Sometimes the car dealership down the way puts BMWs on sale. When they do I don't rush out and buy one. They're fine cars and if anyone wants to give me one, I'll be grateful, but whether it's a $65,000 BMW or a $59,000 BMW makes no difference because I can't afford either one. It's possible when the Red Sox got to the bargaining table and saw Lester's price tag, the discount didn't matter because the price was just too high.

This is bugging me though because, baring something nuts at the negotiating table, the price shouldn't have been too high. The Red Sox are in a great position regarding their farm system. Their Triple-A team features four highly thought of prospects who could become good major league starting pitchers one day soon. They also have Felix Doubront for three more years after Lester's deal expires, another year of John Lackey at the league minimum (with a chance to leverage that into a cheap-ish extension), and Clay Buchholz will be around through the 2017 season. They have options, is what I'm saying. Lots and lots of options. And with starting pitchers, you need lots of options. That's great. It's all great and the organization is better off for all of it. But none of it is likely to replace the quality and quantity that Jon Lester provides.

We'd all love to think differently, but the chances that just one of Matt Barnes, Anthony Ranaudo, or Allen Webster turns into a number three starter are not all that high. It's even money they're all relievers in the long run. All those guys have talent, but ain't one of them a sure thing. Even sure things aren't sure things when you're talking about minor league pitchers. In Lester the Red Sox have a guy they know can throw lots of good innings, who came up in the organization, who beat cancer as a Red Sox, who is a good guy, a strong citizen, a positive in the clubhouse, and a leader on the pitching staff. What's more, because of those young pitchers and their young hitting brethren, the Red Sox payroll stands to shrink in the coming seasons. That's not a reason to throw money away, but it does mean the team will have money to spend. What better way to spend it than on Jon Lester?

The guys at Sons of Sam Horn were discussing this and whether they'd rather have probable free agent Max Scherzer or Jon Lester. No doubt Scherzer is an amazing talent and he is probably the better pitcher going forward, except there are a few mitigating factors. You can guess what they might be, but the point isn't to compare the two pitchers, so much as to say that the Sox know Lester. They've seen him excel under the bright lights of October, they've seen him struggle and come out the other side to succeed again, they've seen him face the strongest lineups in the game, and they've seen him do all these things year after year after year. What's more, they've got him now! Right now! He's sitting at the negotiating table, pen in hand, saying "I want to be here." They have the money, they have the need... and yet, nothing.

I don't want to see Jon Lester in pinstripes. I don't want to see Lester in a Mariners hat. I want Jon Lester, ace or not, to stay with Boston because it's what I want, but also because it's what I believe is best for the team. Sometimes it's difficult to separate analyst and fan. In this case, there's no need to separate because we both want the same thing. The Red Sox should sign Jon Lester, and if they don't do it soon, they're going to regret it.