Boston Red Sox: The Jon Lester Conundrum

Brief confession: I hate the MLB Trading Deadline.

I don’t mind it in theory, and if I was a casual fan with no team allegiance, it would be a blast to see how the league scrambles to make tiny adjustments (or huge-dynamite-blow-it-up moves) for a playoff push.

I hate it like I hate rollercoasters. There fun in theory, but most of the time I just close my eyes, wait for that sinking feeling, and just really hope that there’s not a loose screw somewhere on the tracks that’ll throw us off (this is not a rational hatred I guess).

And as a Red Sox fan, and as a Red Sox fan this year in particular, I hate it even more.

Why? Because Jon Lester is on the trade market. The 30-year old’s contract is up after this season, and he, along with Max Scherzer, figure to be two of the top earners this offseason. With the Red Sox out of the playoff hunt entirely at this point, would-be playoff contenders are circling like vultures to try and nab Lester, even with the knowledge that it could be for only a 3-month rental.

But the thought of Jon Lester in a different uniform makes me sick. More so than seeing Iggy go last year, or Peavy go this year. More so than Ellsbury in pinstripes. A billion times more than the Beckett/A-Gon/Crawford express heading west (though, if you’re like me, you watched that Beckett no-hitter like you’re attending your ex’s wedding: totally happy for him, but sadly remembering what could have been).

And that’s because, next to David Ortiz and Dustin Pedroia, Jon Lester is the Boston Red Sox. While the former two have struggled, the fiery left-hander has grabbed the mantle of face of the franchise, and run with it proudly.

But this isn’t a question that can simply answered by sentimental reasons. In fact it’s two separate questions, both hinging on this week’s action.

First off:

Should the Boston Red Sox re-sign Jon Lester?

The argument against extending a pitcher entering his thirties is well documented, as well as wildly convincing. There have been apocryphal stories over the years from pitchers like Barry Zito to Johan Santana to Mike Hampton. Matt Cain and Justin Verlander, fresh off of extensions, are having miserable seasons for their respective teams. The best case scenario for extending a pitcher is Cliff Lee, who signed a 5yr/120mil deal three years ago, when he 32 years old, and has been just as good, if not better, than he was before it.

imagesThe worst case scenario may be CC Sabathia. The 28-year old Sabathia, one of the most dominant pitchers in the game, signed a 7 year contract with the Yankees in 2009. Through 2012, it looked like a great deal, as Sabathia put up a 3.22 ERA and even led the team to a World Series. The last two years, however, have been nothing short of disastrous, as Sabathia’s era has skyrocketed, and his ailing knees may lead to the premature end to his career.

With that in mind, should the Red Sox bite the bullet and extend Jon Lester?

Yes, yes of course they should.

Let’s talk about the Jon Lester on the field. This year, in his 30th year, Lester has been at his best, posting career bests in ERA (2.52), WHIP (1.119), and SO/W (4.66). He’s also been solid as a rock, tied for sixth in the MLB in quality starts (16), and named an AL All-Star for his efforts.

On top of that, he’s a proven playoff pitcher. We all remember his 2007 World Series-clinching start at the age of 23, only two years after being diagnosed with lymphoma. And last year’s playoff performance was a genuine masterpiece, making 5 starts with 29 strikeouts and a 1.54 ERA.

To put it another way, if Lester was 25 and looking for an extension, this wouldn’t even be a conversation. It seems that it’s the years, and not the money, is the sticking point. But there’s no way around it, the Red Sox’ 4 yr/70 mil offer was an insult. And if the report that Lester, in spring training, would have accepted an offer of $1 more than Homer Bailey‘s 6 yr/105 mil, than the team passed up on a huge opportunity.

The fact of the matter is, retaining Lester will undoubtedly be expensive as well as a risk. But, even if this is a deal that would only definitely pay dividends in the short term (if, like Sabathia, Lester just falls apart in 3-4 years), it’s the short term that is incredibly important for this Red Sox team.

boston red soxRemember, last year’s World Series win was a huge surprise, this is a team that (was) willing to make economic and team-centric decisions, while preserving a deep and talented farm system (that has now only improved with the additions of Edwin Escobar and Heath Hembree). With aging veterans like David Ortiz, Shane Victorino, Jonny Gomes, and John Lackey not definite staples on the team moving forward, the team desperately needs a veteran alongside Dustin Pedroia to act as a bridge from one era to the next.

With the seemingly innumerable starting prospects milling about in Triple/Double A this season, it’s tantamount that the Red Sox have a stable, consistent veteran to man the rotation. We’re going to see a lot of mixing and matching, callups and demotions, and the odd spot start in this next year, as Brandon Workman and Rubby De La Rosa make a case to keep their spots, and Anthony Ranaudo, Allen Webster, Henry Owens, Matt Barnes, and Edwin Escobar try and make a case to obtain one.

The hope was that Clay Buchholz could be that guy, but with his injury history and consistency issues, that seems like a huge stretch. John Lackey would be an ideal candidate, but at 35 and already publicly mulling retirement, how long will he be around? Jon Lester, on the other hand, is the perfect candidate to be the Red Sox ace, which is not just a great pitcher, but a great leader. Remember, this is a guy whose teammates can’t stop praising, who’s beaten cancer to be a star in the MLB, and who’s fresh off of one of the best 12-month stretches in Red Sox history.

downloadNot to mention that he loves playing in Boston and has proven success here. We’ve seen plenty of star players flame out under the scrutiny of Boston’s fanbase (poor, poor Carl Crawford), here we have one who positively thrives under it. Lester’s been extremely vocal about his desire to stay in Boston, and is someone who clearly values his comfort in an environment over top dollars (within reason, of course).

Let’s say Jon Lester turns into CC Sabathia, which is the worse case scenario. Even if the contract is for six years, it’s the next two or three that will absolutely worth it, as the team can lock down one of the MLB’s premier starting talents, as well as a top-of-the-line mentor and leader for a soon-to-be extremely young Boston rotation. And, to boot, he’s a workhorse, a proven playoff warrior, and the model of consistency, who doesn’t have the injury concerns or volatile form of some of his contemporaries.

You don’t quibble about risk at that point. That’s not something you can find on the open market. You don’t refuse to re-sign Lester and then trade away top prospects for his replacement. Extend the man.

And now the second question

If the team can’t come to an extension agreement this week, should they trade him?

Well, don’t get whiplash from this turnaround, but the answer to this one is yes as well.

The tricky thing about this whole situation, from a fan’s perspective, is we don’t really know what’s been said between the two parties. Everything we do know has been released as a ploy to gain leverage, or occurred months ago. We have no way of knowing the exact figures of the potential deal, or whether a potential deal has been put on the table.

But in the last week, every person involved (Lester, Cherington, the owners) has come forward, and said that no deal will be done until the season is over (as far as we know, things can still change, blah blah blah).

And make no mistake, this is terrible news for the Bring Lester Back camp. Because if Lester hits the open market in the winter, no matter how much he says he wants to re-sign with the Sox* , it’ll be hard for him to turn an absurd contract to return. And there will be a team more than willing to throw an absolutely ridiculous amount of money at Jon Lester, no doubt about it (cut to Brian Cashman cackling with glee).

*(My favorite sub-plot in all of this is just how Lester is handling this. By proclaiming loudly how badly he wants to stay in Boston, even going as far to say that, even if he’s traded, he’d still have Boston as his no.1 free agent destination, he’s definitely lowering his trade value a bit. While there are obviously plenty of teams who’d trade for him even knowing it was a three-month rental, it does change things a bit. Is it his final push for an acceptable extension offer from the Sox? A way of forcing the Sox’s hand further? Or part of Ben Cherington’s elaborate plan to get top prospects for nothing.)*

If the Red Sox can’t even pony up 5 yrs/120 mil (a pretty reasonable offer, in my humble opinion), they won’t be able to jump in when that number jumps up an extra year or two, or 50-60 million more. No, if the Red Sox know for certain that they can’t come to an extension agreement in the next few weeks, they can’t risk him hitting the market and signing elsewhere. It’s bad to lose a star pitcher, it’s worse to lose him for nothing. If talks are really as far apart as reported, (know this breaks every part of me) they have to trade him.

download (2)Obviously you can’t just give a pitcher like Lester away, but luckily there are a ton of would-be contenders who would love to have a pitcher like Lester on their squad come playoff time, as well as several teams with the pieces to make it worth the Red Sox’ while. The LA Dodgers, should they miss out on David Price, would love to go all in on a World Series, with either Matt Kemp or Joc Pederson as a package centerpiece. The Seattle Mariners, suddenly a contender, could offer Taijuan Walker, James Paxton, or Danny Hultzen, and jump at the chance to bring Lester to his home state. Same goes for playoff hopefuls Kansas City, Baltimore, or the Angels.

Looking at similar hauls for starting pitchers at the trade deadline, there’s no question that the Red Sox could receive an unbelievable bounty for their star.

But whatever package is out there shouldn’t be the only reason to deal Lester. Only if the team is certain that they can’t work out a deal this season should a Lester trade even be considered. But if they can’t reconcile, then they have to trade him.

And so now the clock is ticking. It’s a monumental decision, and one that may come to bite them either way, but it’s one that has to be made in the next three days.

Like I said, I hate the trade deadline.