Offseason Outlook: Boston Red Sox

Longtime GM Theo Epstein is gone and recently-appointed replacement Ben Cherington will try leading the Red Sox to their first playoff appearance since 2009 by improving the pitching staff and tinkering with the offense.

Guaranteed Contracts

Arbitration Eligible Players (estimated salaries)

Contract Options

  • Dan Wheeler, RP: $3MM club option with no buyout (Type B)
  • Marco Scutaro, SS: $6MM club option/$3MM player option with a $1.5MM buyout (Type B)

Free Agents

To fully understand the challenges the Red Sox face this offseason, we must review the events of the past two months. Red Sox fans already know the unpleasant details, so I'll be brief: since the beginning of September, the Red Sox — a franchise no longer accustomed to losing — lost 20 games and their seemingly unshakable grip on a postseason berth. Days after the collapse, they lost their manager and within weeks their longtime general manager left, too. Now, they're about to see their designated hitter and closer hit free agency along with franchise icons Tim Wakefield and Jason Varitek.

No, Cherington's first offseason in the GM's office won't be an easy one. But unlike his predecessor, Cubs president of baseball operations Theo Epstein, Cherington doesn't face anything resembling a rebuilding process. Despite the chaos of the past eight weeks, Boston is well-positioned for success in 2012 and beyond.

It starts with the search for a new manager: someone who can restore order in a clubhouse that apparently featured more than its share of beer and fried chicken in 2011. Boston's search is in its early stages, with the team set to conduct first-round interviews soon.

The September version of the Red Sox played roughly at the level of the 1962 Mets or 2003 Tigers. A whole lot went wrong down the stretch, so it would be unfair to put all the blame on Boston's starting rotation. But make no mistake — Cherington must obtain starting pitching this winter. Pencil Jon Lester, Josh Beckett and Clay Buchholz in and you have three above-average starters leading the rotation, as long as Buchholz recovers from the lower back stress fracture that sidelined him at the end of 2011. John Lackey and Daisuke Matsuzaka will be recovering from Tommy John surgery, which leaves two openings in Boston's rotation.

Reinforcements could come internally, where the Red Sox have Andrew Miller, Kyle Weiland and Felix Doubront. They could re-sign Wakefield, since the knuckleballer contributes every season and was his usual self in 2011, even as a 45-year-old. Cherington will be looking for more.

At his introductory press conference, the new GM suggested he'll search for buy-low starters. Perhaps this means the Red Sox will offer veteran starters one-year deals and hope for better results than John Smoltz and Brad Penny provided in 2009. Roy Oswalt could be an option, if the Red Sox believe his back is healthy. 

As usual, the Red Sox and Yankees engaged in a bit of gamesmanship at the other's expense last offseason. Boston expressed interest in Mariano Rivera and New York drove up the price for Carl Crawford. Boston should inquire on C.C. Sabathia if he hits the open market this offseason. Sabathia could help the Red Sox and interest from Boston would at least drive the price up for the Yankees, if they successfully re-sign him. While the Steinbrenners spend more than any owners in the game, there's no harm in making the Yankees pay more than they'd like to.

Cherington hasn't publicly ruled out the pursuit of other top free agent starters and until he does, the Red Sox will be linked to the likes of Yu Darvish, C.J. Wilson and Edwin Jackson. The team could also try luring Hiroki Kuroda to Boston, though he appears to favor Los Angeles. 

The Red Sox could inquire on any number of trade candidates, including Fausto CarmonaJonathan Sanchez, Ricky Nolasco and White Sox starters Gavin Floyd and John Danks. Though Orioles right-hander Jeremy Guthrie and all the Rays' starters are likely off-limits, the Red Sox should check in on the best arms available on the trade market. Unfortunately for them, the Yankees will be doing exactly the same thing. Depending on how the Red Sox approach their offseason, Jed Lowrie, Ryan Lavarnway, Ryan Kalish and Josh Reddick could all be viewed as expendable in trade talks.

Jonathan Papelbon has anchored Boston's bullpen since 2006 and he recorded the final out of Boston's 2007 World Series championship. However, it's no secret he wants to follow the money and the Red Sox have a ready-made replacement in Daniel Bard, who should be fine in 2012, despite his awful September. Boston will surely offer Papelbon arbitration, as he's a Type A free agent, but I'll be surprised if he reports to Fort Myers with the Red Sox next Spring Training.

Like the rotation, the bullpen requires some offseason work. Bard, Alfredo Aceves and Franklin Morales will return and the Red Sox can hope for more from Bobby Jenks in 2012. Dan Wheeler, a valuable yet replaceable reliever, projects as a Type B free agent, so the Red Sox could decline his option and offer arbitration. This would assure them of one of two acceptable results: a draft pick or one more year of Wheeler at an affordable rate. Cherington will likely pursue relief pitching even if Wheeler and non-tender candidates Miller and Matt Albers return.

Lost in the drama of the past two months has been Boston's impressive offensive output. The Red Sox scored more runs than any team in baseball in 2011 and with most of their core players returning, there's no reason to believe they won't have one of the league's best offenses again. The Red Sox are likely to exercise Marco Scutaro's option for $6MM. This would give Jose Iglesias more time to develop and relegate Lowrie to the bench. The rest of Boston's infield is set, with Adrian Gonzalez at first, Dustin Pedroia at second and Kevin Youkilis at third.

The outfield features the American League's most surprising player this side of Mike Napoli and its most disappointing player this side of Adam Dunn, in Jacoby Ellsbury and Carl Crawford, respectively. Likely joining the two as starters is Reddick, who hit .280/.327/.457 in roughly half a season of playing time. The Red Sox may explore an extension for Ellsbury, not that negotiating with a Scott Boras client coming off of an MVP-caliber season would be easy.

After yet another productive season, David Ortiz is the top designated hitter available on the free agent market. He posted a .309/.398/.554 line, and even though he turns 36 this November, he seems well-positioned for a generous contract. Will the Red Sox finally provide him with the long-term deal he's been seeking for years? Maybe. They'll probably start by offering arbitration, an advisable move given Ortiz's power. But there's no sense in overcommitting to a positionless player who may be approaching his decline phase, so expect the Red Sox to be prepared to walk away. Other free agent DHs are available and Lavarnway is an internal candidate for the job, so Boston isn't bound to Ortiz. 

When he introduced Boston's new general manager, Red Sox president and CEO Larry Lucchino pointed out that Cherington will not have the luxury of a peaceful start. “He will hit the ground running, in full stride, and no one will outwork him,” Lucchino said. The way the 2011 season ended, there's no other choice.


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