Predicting Ben Cherington's Plan of Action the Rest of the Red Sox's Offseason

Zachary D. Rymer@zachrymerMLB Lead WriterDecember 27, 2012

BOSTON, MA - OCTOBER 23:  Executive Vice President and General Manager of the Boston Red Sox, Ben Cherington, listens after introducing John Farrell as the new manager, the 46th manager in the club's 112-year history, on October 23, 2012 at Fenway Park in Boston, Massachusetts.  (Photo by Jared Wickerham/Getty Images)
Jared Wickerham/Getty Images

One of these days, Boston Red Sox general manager Ben Cherington will get to sleep again.

But not yet. It's been a busy offseason for Boston's second-year GM, but he still has miles to go and roster spots to fill before he sleeps. He's done a lot, but his checklist isn't complete yet.

With one notable exception—hint: first base—the Red Sox are pretty much out of excuses to make major transactions at this point in the winter. From now until pitchers and catchers report, Cherington will just be busy tying up loose ends and fine-tuning his roster for the 2013 season.

Here's a look at what his plan of attack from here on out probably looks like.


Phase 1: Finish Mike Napoli's Deal

Mike Napoli's deal isn't final yet. But don't worry; it soon will be.

The Red Sox have still not finalized the three-year, $39 million contract they and Napoli agreed to earlier this month. It's hit a snag, and the vibes surrounding the deal are less than encouraging.

Last week, Ken Rosenthal of reported that an issue with one of Napoli's hips is holding up the completion of his deal. Cherington has admitted that the two sides are working through some "issues," and signs point toward that meaning either inserting protective language into Napoli's deal or re-working it entirely.

The Red Sox also have the option of backing away and pursuing somebody else, and they may do that. 

As first reported by Jen Royle of SB Nation Boston and confirmed by Rosenthal, the Red Sox are still talking to free-agent first baseman Adam LaRoche, who hit a career-high 33 homers and won a Gold Glove in 2012 with the Washington Nationals.

Rosenthal, however, says that the Red Sox view LaRoche as an alternative rather than as a primary target. Apparently, they still prefer Napoli.

As well they should. Napoli may not be healthier than LaRoche, and he's certainly not a better defender, but he does have some advantages. One is that he's two years younger than LaRoche. Another is that he's a better fit for Fenway Park, a ballpark that he has owned during his career.

Just as important, the Red Sox won't have to forfeit a draft pick if they complete their deal with Napoli. They would if they signed LaRoche instead.

Napoli could pull away from the table before the Red Sox do, but it's unlikely that he will. He doesn't want to re-enter the market after all this drama with the Red Sox, as teams will be well aware that not even a team that was looking to overpay him a little wanted to take a chance on him after taking a closer look. He'd surely have to settle for a much, much lesser contract.

Napoli's best bet is to compromise with the Red Sox, and the best thing for them to do is compromise with him. It may take a little while, but a deal will get done.


Phase 2: Find a Left-Handed Platoon Partner for Napoli

The Red Sox will have a new starting first baseman once they complete their deal with Napoli, but their first base depth chart will still need some work. 

For starters, it will simply need more depth. The only true first baseman the Red Sox have on their 40-man roster right now is Mauro Gomez, and he barely qualifies as a "true" first baseman. He's more of a designated hitter-type player.

Besides which, Gomez is another righty hitter. If the Red Sox are going to commit to Napoli at first base on a full-time (or semi-full-time) basis, they're going to need to bring in a left-handed platoon partner. The only lefty-hitting infielders they have on their 40-man now are Stephen Drew and Brock Holt, both of whom are middle infielders.

This isn't an area where the Red Sox will have to break the bank. They can go for a cheap one-year option on the free-agent market, and there are still some players out there who fit the bill.

For example, former Red Sox Casey Kotchman could be open to a platoon job. He's had rough seasons at the plate two of the last three years, but he had a highly successful season in 2011 with the Tampa Bay Rays, and he still bears a solid glove.

Also out there are Aubrey Huff and Dan Johnson. Neither of them has much upside, but Huff might still have some pop in his bat, and Johnson at least has a flare for the dramatic.

Jason Giambi and Lance Berkman are also possibilities, albeit not likely ones. Both of them are over the hill, and they may not be willing to take jobs as platoon players at this stage unless they see a legit chance to win a ring. The Red Sox can't offer that.

Whoever Cherington brings aboard, this is definitely a need that won't go unfilled. 


Phase 3: Deal a Reliever

Remember when the Red Sox's bullpen didn't have enough talent in it?

Things are a little different now. The Red Sox have an All-Star closer in Joel Hanrahan after this week's trade with the Pittsburgh Pirates, a former Rookie of the Year in Andrew Bailey, two underrated right-handers in Koji Uehara and Junichi Tazawa, two solid lefties in Craig Breslow and Andrew Miller, a versatile right-hander in Alfredo Aceves and a bounce-back candidate in Daniel Bard.

I think that's everyone. Even if it's not, you get the point. This is a deep bullpen.

Too deep, in fact, and that's something the Red Sox can take advantage of. Pete Abraham of The Boston Globe has the right of it in noting that Boston's bullpen has a couple dealable assets:

Tradeable #RedSox pieces: One of the catchers, Aceves, Bailey, one of the lefty relievers.Not sure what that adds up, however.

— Pete Abraham (@PeteAbe) December 27, 2012

Dealing a reliever could be a way for the Red Sox to fill their need for a lefty platoon partner for Napoli at first base if they don't like their free-agent options. They could also package a reliever with an expendable player (i.e. Jose Iglesias, Franklin Morales, et al) and set their sights a little higher.

For example, the Red Sox could make a play for one of the Los Angeles Dodgers' excess starting pitchers. Danny Knobler of has reported that both Chris Capuano and Aaron Harang are available.

The Red Sox could just keep all their relievers and move forward with an uber-deep bullpen, but it's better to have rotation and lineup depth than it is to have bullpen depth. If the Red Sox can sacrifice some of their considerable bullpen depth to upgrade their roster elsewhere, they will.


Phase 4: Get Extension Talks Going with Dustin Pedroia

Once Cherington is finished rounding out the club's roster, he can turn to internal matters.

An extension for Dustin Pedroia could be in the cards before the 2013 season opens. Joe McDonald of reported earlier this winter that the Red Sox were considering getting something done once everything else on their offseason docket had been taken care of.

It makes sense for both sides to sit down and hammer something out sooner rather than later. The Red Sox have to be mindful of the fact that Yankees star Robinson Cano is poised to set the market for elite second basemen next winter.

Pedroia, meanwhile, has to be mindful of the fact that he's had issues with injuries two of the last three years and that he won't be hitting free agency until he's in his early 30s. If the Red Sox want to pay him a ton of money now, he would be wise to take it.

Pedroia is on the books for $10 million in 2013 and 2014, and the Red Sox hold an $11 million option for him in 2015. An extension would likely be for something more like $15 or $16 million per year, a la the average annual value of the extension Ian Kinsler signed with the Texas Rangers in April.

The Red Sox might even be willing to overpay Pedroia because of what he means to the organization from a leadership perspective. Even if he breaks down physically, he could still be a valuable member of the team because of his presence in the clubhouse.

While the Red Sox are at it, they should also consider extending the youngster at the hot corner.


Phase 5: Lay Groundwork for a Will Middlebrooks Extension

He only played in 75 games as a rookie in 2012, but Will Middlebrooks was a huge bright spot for the Red Sox in what was otherwise a dreadful season.

The 24-year-old posted an .835 OPS and hit 15 home runs, and he also showed some promise on defense. A small sample size, to be sure, but good enough to entertain notions of an All-Star future.

The Red Sox don't have to worry about Middlebrooks hitting free agency for many more years still, but they could do themselves a favor by jumping the gun and signing their young third baseman to a team-friendly extension. They could lay groundwork for such an extension now and move forward with it once the 2013 season is underway.

The Red Sox could take a Rays-like approach to an extension for Middlebrooks by looking to lock him up at reasonable rates through his arbitration years. They could even look to lock him up through a couple of free-agent years (i.e. 2019 and 2020).

The longer the Red Sox wait to extend Middlebrooks, the more they risk his price tag getting higher than they would prefer. There's also the possibility that Middlebrooks will be more inclined to hit the open market than to sign an extension as he gets closer to free agency.

There's some risk in extending him sooner rather than later, but not much. The Red Sox wouldn't be locking him up for an absurd amount of money—$100 million or so—meaning that Middlebrooks' contract wouldn't be a huge burden if he fails to pan out.

Given the amount of young talent the Red Sox have down on the farm, "lock 'em up while they're young" could be the club's mantra before long. It's in their interest to get some practice in now with Middlebrooks.


Note: Stats courtesy of unless otherwise noted. Salary and payroll information courtesy of Cot's Baseball Contracts.

If you want to talk baseball, hit me up on Twitter.

Follow zachrymer on Twitter


    Tommy Layne Signs Minor League Deal with Red Sox

    Boston Red Sox logo
    Boston Red Sox

    Tommy Layne Signs Minor League Deal with Red Sox

    Ohtani Surrenders HR, Strikes Out 2 in Debut

    MLB logo

    Ohtani Surrenders HR, Strikes Out 2 in Debut

    Mike Chiari
    via Bleacher Report

    Ten Ways to Improve Major League Baseball

    MLB logo

    Ten Ways to Improve Major League Baseball

    Clarity Could Come on Martinez on Saturday

    MLB logo

    Clarity Could Come on Martinez on Saturday

    NBC Sports Boston
    via NBC Sports Boston