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Red Sox need to move past fear, extend Jon Lester

Or "how I learned to stop worrying and love the big contract."

Jim Rogash

Are you one of the last remaining holdouts? When your friends talk about re-signing Jon Lester, do you just smile and nod? Can you not look at talk of a six-year contract without feeling physically ill? Do visions of nine-digit numbers keep you up at night?

I was in the same boat not long ago. I wanted Jon Lester to stick around, but I also felt deep down that there was no way he would agree to stay at a price I was comfortable with. Having been burned by Beckett before, having lived through the debacle of the 2011-2012 offseason, I never wanted to see the Red Sox sign another huge contract with anyone short of Mike Trout. And certainly not with a pitcher who we had seen struggle throughout most of 2012 and even a good chunk of 2013. If he was serious about taking a home-team discount we could talk, but as it became clear the Red Sox would have to match market value to retain Lester's services, I started thinking seriously about replacements.

Two starts ago I finally broke. I don't know why it was that start which pushed me over the edge. Lester had already long since established himself as one of the season's best arms. In fact, the earned run Lester allowed that night was his first in nearly three weeks. Still, for whatever reason, that one start against the White Sox was enough:

So there's the emotional leap made. Now how about the logical end of things?

A big part of getting to this point just has to do with time. It's been a year now since Lester last slumped in the middle months of 2013, and that year has not only seen Jon Lester return to his usual form, but rise well above it. The season that is Lester's last 365 days has seen him throw 216 innings of 2.62 ERA baseball, striking out 208 batters while walking just 51. And that's not including his ridiculous postseason run! To make a long story short, it's a lot easier to write off 2012 as just being one more symptom of the terrible state the club was in, to say nothing of some bad luck.

Honestly, though, the minutiae of Lester's performances are a less important factor than the situation the franchise is in as a whole. At this point, every new amazing start from Lester is less and less impactful. He's long since established that he's quite the pitcher, but he's not going to convince anyone who's not already convinced that he's actually the best the American League has to offer after Felix Hernandez in any given start. There are limits, basically, in what an outlier year can do for a player's reputation. For instance, I'll admit that I'd still take Yu Darvish over Lester.

But Darvish is not on the table, and if Lester's superlative year can only do so much to change how he's perceived, his reputation didn't need much of a boost to begin with. So let's talk payroll.

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Photo Credit: David Butler II

Jon Lester is going to take a lot of money to sign. Let's go ahead and ballpark him at six years and $150 million to be conservative (in his favor). So what does that do to Boston's payroll? Well...not all that much, honestly. In 2015 the Red Sox are on the line for some $75 million. That's good for two starting pitchers, two infielders, a designated hitter, an outfielder, and a reliever that, trust me, you really don't want to talk about.

So that leaves two outfielders, two infielders, and a catcher needed just to fill out the starting nine. Well...Xander Bogaerts and Jackie Bradley Jr. seem like locks for two of those spots right now barring a serious change of long-term plans. Christian Vazquez will factor into the catching situation, too, leaving us with just an outfielder, infielder, and a few bench players needed to fill out the offense. And no, we haven't even mentioned top prospect Mookie Betts, the ever-versatile Brock Holt, or the resurgent Daniel Nava who, as the most expensive of the trio, might cost the Red Sox a couple million dollars in arbitration.

Then there's the rotation. Maybe the Red Sox have to reinvest in Lackey to keep him aboard, but their option should still get them a reasonable discount. And behind him and Buchholz the Red Sox have:

  1. Brandon Workman
  2. Rubby De La Rosa
  3. Allen Webster
  4. Anthony Ranaudo
  5. Henry Owens

There are plenty of names waiting in line to pitch for the Red Sox for very little money. The Red Sox aren't going to need to dump $10-$15 million into the back-end of their rotation to get some decent innings out of it.

That leaves the bullpen which, while it might need a serious overhaul in 2015, is also not the sort of thing the Red Sox will be sinking $40 million into. It's just not going to be enough to change the overall picture of a young team reaping the financial benefits of a productive farm system. The Red Sox have a lot of money to work with, but can expect to have much of their roster filled by young, inexpensive players going ahead. That leaves Boston with plenty of financial resources but relatively few roster spots to spend them on, needing to avoid the pitfall of being consistently decent but never great.

The math, then, is simple. High-priced free agents are actually the perfect complement to a farm system that's capable of filling significant portions of the roster. They manage to cram the most value into, essentially, the smallest space. In 2013, the Red Sox needed to take a more shallow approach, trying to patch up plenty of holes with above-average players. Now they're in the opposite situation, needing to fill few holes with as much quality as they can find.

Jon Lester obviously fits that bill. Moreover, he's the only player who does so without any question that he can play in Boston. Even if the Red Sox lock him in for $25 million, they're still going to have one hell of a time trying to reach the CBT threshold that has, for years, been their effective salary cap. And even if it takes six years to keep him on board, his contract will be running out at around the same time the bulk of Boston's young players start hitting free agency, freeing up funds to make sure the most important of them stick around.

It's getting harder and harder to find marquee talent in free agency these days. That makes the ability to develop talent internally that much more important, but it also means that allowing a marquee player like Lester to hit free agency is that much less acceptable. Back when the market was flooded with big-name mercenaries, a star player signed to a star's contract was not a commodity. But for a Red Sox team with a lot of money to spend and relatively few outlets on the horizon, that's just not the case anymore.

The Red Sox are right to be wary of committing both dollars and years to big-name free agents. But they can't let that wariness cripple them, especially when they're in a situation which so clearly favors making a few major acquisitions rather than a number of mid-range ones. Unless the Red Sox know something we don't about his demands or his arm, it's time to stop worrying and just sign Jon Lester.