Last week, I wrote about how the Red Sox are in great shape headed into the offseason thanks to their financial and organizational flexibility. With the Nick Punto trade creating more salary relief than anyone would’ve thought possible and a big steps forward by a majority of the Sox’ better prospects this season, Boston is in an enviable position when it comes to building a roster for 2014 and beyond.

A big part of that strategy revolves around whether Jacoby Ellsbury resigns with the Red Sox after this season.

You already know the details surrounding Ellsbury, so I’ll just gloss over them here: it was once considered a foregone conclusion that he would leave for greener pastures after 2013, but now there’s a prevailing sentiment that the Red Sox at least have a shot
at retaining Ellsbury past this season. There are three primary events over the past year that have shaped this new line of thinking:

1) The aforementioned trade with the Dodgers, in which the Red Sox freed up a tremendous amount of money, but also lost two left-handed bats in Adrian Gonzalez and Carl Crawford
2) Ellsbury’s own performance this season, which will essentially split the difference between his superstar campaign in 2011 and his frustrating, injury-riddled season in 2012
3) The Red Sox’ performance in 2013, which sees them no longer as a rebuilding club but rather as one that’s poised to compete for the next several years

Jacoby Ellsbury is undeniably handsome. Photo by Kelly O'Connor,,

Jacoby Ellsbury is undeniably handsome. Photo by Kelly O’Connor,,

Pegging down the type of contract Ellsbury is going to receive is quite difficult. The whispers of a Carl Crawford-type megadeal that persisted after 2011 seem farfetched now. Ellsbury has been worth more than 2.5 fWar exactly three times in his career now – 2008, 2011 and this season – and played in just 92 games in 2010 and 2012 combined. The prodigious power we saw during his 32-homer, .552 SLG season in 2011 looks to be a mirage, and Ellsbury is more likely to hit for 8-15 homers a year as we’ve seen him do in 2008, 2009 and 2013.

That being said, when he’s healthy it’s hard to argue against placing Ellsbury among the best outfielders in the game. His 4.7 fWAR this season ranks 16th in all of baseball, fifth among outfielders and fourth among center fielders. Those ahead of him include bonafide superstars in Mike Trout and Andrew McCutchen and then Carlos Gomez, who is having a career year.

Red Sox fans generally rationalize accepting Ellsbury’s absence by stating that Jackie Bradley Jr. is waiting in the wings and can easily fill in as a replacement. While I agree that Bradley can hold down a starting center fielder job for a contender, we shouldn’t confuse his upside with what Ellsbury can bring to the table. The argument should be that Bradley can produce 70% of what Ellsbury can do at a fraction of the cost. It should not be that Bradley can reasonably recreate what Ellsbury brings to team at the plate or on the bases.

I do not know what type of contract Ellsbury will receive this season, and I won’t explore it in depth here because that’s a column in and of itself. My guess is the five-year, $75.5 million contract B.J. Upton signed this offseason is probably a floor, and that something in the vicinity of $17-18 million per season is the ceiling.

We know that Ellsbury will have no shortage of suitors, and that teams with serious financial muscle can compete with Boston for his services. We also know that Ellsbury is probably the second-base player on the free agent market, trailing only Yankees second
baseman Robinson Cano. The market for Ellsbury this offseason is going to be heated, and there’s no reason to think that anything resembling a hometown discount is going to come into play. If the Red Sox want Elllsbury, they’re going to have to pony up.

And in my opinion, they should.

When the Red Sox enter the offseason, they’ll be faced with holes at catcher, first base and center field, assuming that Xander Bogaerts will begin 2014 as the everyday shortstop and Will Middlebrooks as the everyday third baseman. They have six starting pitchers who are league average or better, a fairly deep bullpen and an insane amount of pitching depth in the upper minors.

Boston could opt for a big splash and go after Brian McCann, or perhaps they’ll pursue the newly available Jose Dariel Abreu to play first base. I think the latter is more likely
to happen than the former, given the Sox’ plethora of left-handed bats. Perhaps they’lldiversify their spending like last offseason and sign veterans with upside to more modest deals.

But I’d argue that Boston’s best option is to resign the occasionally frustrating but very steady Jarrod Saltamaccchia, then make a big push for Ellsbury and use what they have to fill their 1B hole.

It’s not a perfect scenario, but this would allow Mike Carp to start against righties – an opportunity he very much deserves – and give Daniel Nava at-bats against lefties. Nava hits better against righties than southpaws, to be sure, but he’ll likely put up more of a fight than would Carp against same-side pitching.

Here’s how the Sox could configure this sort of platoon. What you see below would allow for more frequent days off for the fragile Shane Victorino as well.

Against LHP
1B: Nava
LF: Gomes
RF: Victorino (Bradley)

Against RHP
1B: Carp
LF: Jackie Bradley Jr.
RF: Victorino (Nava)

And here’s a look at how the lineups would play out 1-9.

2014 Red Sox vs. RHP 2014 Red Sox vs. LHP
Jacoby Ellsbury, CF Jacoby Ellsbury, CF
Shane Victorino, RF Shane Victorino, RF
Dustin Pedroia, 2B Dustin Pedroia, 2B
David Ortiz, DH David Ortiz, DH
Mike Carp, 1B Jonny Gomes, LF
Xander Bogaerts, SS Daniel Nava, 1B
Jarrod Saltalamacchia, C Xander Bogaerts, SS
Will Middlebrooks, 3B Will Middlebrooks, 3B
Jackie Bradley, LF David Ross, C

That’s a pretty daunting lineup for righties to have to go through, and if one of Bogaerts or Middlebrooks really clicks then lefties wouldn’t have the easiest time either. While the Nava at 1B solution isn’t ideal, it’s really the only weak spot I can see at any point on the roster.

And most importantly, Boston keeps its very effective Top 4 in the order from 2013 intact. These lineups possess a really nice mix of power and speed, are fairly balanced in terms of lefties and righties and open the door for interesting late-inning replacements and combinations as well.

Maybe Ellsbury will price himself out of Boston’s reach, or maybe another team will blow everyone away with a deal that pays him like it’s 2011. Perhaps Ellsbury really doesn’t want to stay in Boston and, remembering the ugly incidents with his medicals, will look
for greener pastures.

If it’s at all reasonable, though, the Red Sox are best off splurging to keep their leadoff hitter, center fielder and one of the best homegrown players they’ve produced in the past decade. It’s easy to point out what Ellsbury isn’t or what he might cost, but it’s
hard to like this lineup as much without him.