The complicated case of the next Red Sox ace

The Red Sox are after a free agent ace this offseason, and there's no better time to be in that particular market. Max Scherzer, Jon Lester, and James Shields, to say nothing of also-rans like Francisco Liriano and wild cards like Kenta Maeda.

Those last two categories are not where the Red Sox want to be, however. At least not for the arm they're hoping will anchor their rotation for years to come. No, they're after one of those big three, and they have money to go after any of them if the willingness is there. We all have our favorites (and I'm guessing a majority of those favorites are Jon Lester considering the history there), and there's no question that all three would improve the Red Sox rotation quite a bit. But the question is which one is the best value for Boston?

The issue is that there is no clear case A, B, or C here. It's not Jon Lester, $150/6 vs. James Shields, $100/5. It's all a bunch of guesswork with pretty dramatic ranges.

Let's take Shields as an example. Earlier today, we heard that he's expected to land a five-year deal. That's all well and good, but the price range on those five years was given as $80 to $110 million. That's a ridiculously large difference between the top and bottom mark, and this is just from one report! Maybe Shields could get four years, and we drop the bottom of the range to $68 million. Maybe the pitching market goes nuts and he gets six, leaving us with an upper limit closer to $130 million. It's all one giant mess.

So we can't really say what's best. but we can start to draw lines. Lines where it stops being reasonable to choose one player over another.

Consider, for instance, the case where James Shields is as expensive as that report suggests he could be, coming in at $110 million over five years. That's $22 million per season for his age 33, 34, 35, 36, and 37 seasons.

Now consider the most commonly cited price point for Jon Lester: six years, $150 million. That's $25 million per season for his age 31, 32, 33, 34, 35, and 36 seasons.

The idea that Jon Lester is worth $40 million more than James Shields--a full 36%--seems like an overstatement, which might make Shields seem the better option. But that's not what we're really comparing here. We're comparing Jon Lester's age 31 and 32 seasons vs. James Shields' age 37 season and $40 million, and that's where it starts to seem crazy to sign Shields. Going by age alone, Shields' five years actually carry more risky years than Lester's six. If the Red Sox are as risk-averse as they seem to be, Shields at five years is actually less desirable than Lester at five.

Photo Credit:  Dilip Vishwanat

Of course...that's if Lester comes in at 6/$150. Just as Shields has a high guess, so too does Lester. What if Max Scherzer signs a truly insane eight-year contract and Lester can demand seven as a result? going from 5/$110 to 6/$150 for Jon Lester seems like a no-brainer, but if we start talking 7/$175...well, suddenly that jump is that much more intimidating. Suddenly Lester is locked in for just as long as Shields in terms of age.

There's also the low side of things. Maybe that Shields figure is actually not realistic, and he only gets $80 million over four years. At that point even at six years, the added risk of a Jon Lester contract starts to outweigh the benefit of his age and quality.

The really interesting one for me comes between Lester and Scherzer. With any other team, if those two arms came in close to one another, Scherzer would seem to be the obvious choice. For the Red Sox, though, with Lester's history of success in Boston and in Fenway, it might be hard to imagine the scenario where it's Scherzer donning a Sox uniform in 2015. That may already have seemed incredibly unlikely if you're the sort who thinks the Red Sox will never sign another player to a huge contract while Ben Cherington is around. But even for those who still hope for the top names on top dollar deals, the likelihood of Max Scherzer signing here while Jon Lester is still on the market seems very low indeed.

Frankly, I expect that the most likely combinations of price points would leave Jon Lester as both the correct choice and the probable one when taking his history with the organization into account. But...well, the question of willingness remains, and the idea that Cherington simply won't go to six years is by no means baseless. It's possible that the team would rather give up quality young players for someone like Cole Hamels than tack two more years onto a contract for Lester.

But ideally the Red Sox will simply be looking at this from a slightly more dynamic perspective. Where a high price point isn't just a high price point that shouldn't be met, but is taken in the context of the market that's forming for the other pitchers available. The Red Sox certainly can't go into 2015 with their rotation as bad as it is right now--there's no way to sell that bunch to this fanbase after 2014. And it really does them no good to reminisce about the 2013 season and its many fantastic free agent signings in a market filled with top-quality, top-price arms when it's so clear that the team needs one of them. If that means ponying up six years to Lester or Scherzer, or even five to Shields, then so be it.