Offseason Outlook: Boston Red Sox

After a last place finish in 2012, a heralded offseason helped bring the Red Sox a World Series title in 2013.  What can the Sox and GM Ben Cherington do for an encore this winter?

Guaranteed Contracts

Arbitration Eligible Players (service time in parentheses)

Free Agents

Other Payroll Obligations

A winning strategy always draws imitators, and there's no doubt many clubs took note of how the Red Sox returned to prominence after eschewing big-ticket moves in favor of less-expensive and more measured free agent signings in the 2012-13 offseason.  Adding the right mid-tier free agents can definitely help turn a 69-game winner into a World Series champion in one offseason — just as long as you have the likes of David Ortiz, Dustin Pedroia, Jon Lester, Jacoby Ellsbury, John Lackey and Clay Buchholz already on your roster and they all make big rebounds from down seasons.  While the free agents, improved team chemistry, and addition of John Farrell as manager unquestionably helped, Boston's worst-to-first title run isn't as much a case of a bad team suddenly becoming great as it was a good team getting back on track after a Murphy's Law season in 2012.

The strength of the Sox core is illustrated in their list of guaranteed contracts and the four arbitration-eligible players likely to be tendered contracts.  Those 16 players account for just under $128MM in payroll and only three are guaranteed money beyond next season.  This gives the Red Sox tons of flexibility in filling their few holes, whether it's re-signing some key players, taking on a big salary in a trade or making more forays into free agency.  While their core is strong, the Sox aren't afraid to shake things up in order to make the roster even stronger over the long run.

Let's start with Ellsbury, Boston's biggest internal free agent case.  The Red Sox made at least two attempts to lock up their center fielder before he hit the open market, and now Ellsbury heads into free agency wearing another World Series ring and coming off a .298/.355/.426 season that included nine homers, 92 runs scored and a league-best 52 stolen bases.  MLBTR's Tim Dierkes ranks Ellsbury second on his free agent power rankings and recently guessed that Ellsbury and agent Scott Boras could find a contract in the $150MM range. 

If the bidding goes that high, Boston could be out, as the club is reportedly unwilling to greatly exceed the $100MM threshold for Ellsbury.  I'd still consider the Red Sox as the favorites to sign Ellsbury but it wouldn't be the first time that Boras has scored an inflated contract for one of this clients.  If a team (or teams) push the bidding past $125MM, expect Ellsbury to be playing in another team's uniform in 2014.  It's not that Boston couldn't afford such a contract, but in the wake of the Carl Crawford deal, the Sox are wary about paying a speed-based player big dollars into his 30's.

If Ellsbury leaves, the Sox could give Jackie Bradley a chance at the center field job.  Bradley (a consensus top-40 prospect in preseason rankings from, Baseball America and ESPN's Keith Law) has put up big minor league numbers and could join Will Middlebrooks and Xander Bogaerts as the latest homegrown prospects to step into the Boston lineup.  Bradley could be used in a platoon to begin with, and the Sox could look for a right-handed hitting CF in the mold of a Rajai Davis or a Reed Johnson to add to the outfield depth chart.

Napoli has said he wants to return to Boston, and a reunion could happen if a three-year/$42MM contract is indeed Napoli's price.  There have been rumors, however, that the club isn't keen on giving Napoli three guaranteed years and Boston's pursuit of Jose Dariel Abreu could be a sign that the Sox are ready to move on from Napoli.  Mike Carp dominated right-handed pitching in 2013, though his less-impressive career splits indicate that the Sox would probably prefer to keep Carp as a part-timer rather than a semi-everyday first baseman. 

First base is a relatively easy enough position to fill that the Sox might prefer the compensatory first round draft pick that they would receive if Napoli signs elsewhere.  Stephen Drew, similarly, might not be as valuable to the Sox as a first-round pick, since the presence of Bogaerts and Middlebrooks on the left side of the infield makes Drew's return problematic (barring some position juggling).  Since Drew will draw attention from several shortstop-needy teams, my guess is the Red Sox will move on. 

While Ellsbury, Napoli and Drew received qualifying offers, Jarrod Saltalamacchia did not.  He could be re-signed but a slugging catcher who isn't tied to any draft pick compensation will surely draw a lot of attention from other teams, and another club could very well give him a four-year contract (Boston is reportedly willing to give "Salty" as many as three guaranteed years).  The Red Sox are, however, a team that could be well-positioned to sign Brian McCann.  Boston would have to surrender their first round draft pick (30th overall) to sign McCann but that's no big loss since the club could gain as many as three compensatory picks if Ellsbury, Napoli and/or Drew left.  A five-year, $80MM contract would allow the Sox to install McCann behind the plate for a few seasons until Ryan Lavarnway, Blake Swihart or Christian Vazquez emerges as a catcher of the future, and then McCann could become a DH…provided that the ageless Ortiz isn't still mashing, that is.

Elsewhere around the diamond, if Drew leaves, the Sox are a good bet to sign a veteran infielder who can play either third or shortstop if Bogaerts or Middlebrooks struggles.  The Daniel Nava/Jonny Gomes platoon worked out well in left field and should continue, while it will be business as usual for the trio of Pedroia, Ortiz and Shane Victorino.  It could be argued that Boston's offseason really began when they managed to lock up Pedroia to a below-market extension in July, a move that should aid the Sox payroll for the better part of the next decade.

The team boasts strong rotation depth with Lester, Lackey, Buchholz, Jake Peavy, Felix Doubront, Ryan Dempster and younger arms like Brandon Workman, Allen Webster and Rubby De La Rosa in reserve.  If that wasn't enough, the Sox have checked in on free agent starter Tim Hudson, which would seem to hint that one or more of the current starters could be moved in a trade.  The Red Sox could sell high on Lackey, or perhaps deal Peavy following his postseason struggles.  Dempster would probably be the preferred candidate to deal given rough 2013 season, age (36) and $13.25MM salary.  Boston could try to mine trade value from his durability and home/away splits to prove that Dempster could pitch better in a friendly environment than Fenway Park.

Lester would be an even bigger trade chip if the Sox wanted to really make a splash, and we know that Lester was shopped to the Royals last offseason following his disappointing 2012 campaign.  While Lester could bring back a huge return, it's more likely that the Red Sox will look to extend the southpaw given his return to form in 2013 with a strong regular season and outstanding playoff run.  No talks have yet taken place about another multiyear extension, though the Sox already made the easy call of picking up Lester's 2014 option.

Koji Uehara easily passed the 55-game plateau that caused his 2014 option to vest, and his emergence as a lockdown closer makes his $4.5MM salary for next season seem like a bargain.  Uehara's dominance solved a lot of problems in the Sox bullpen though there will be holes to fill as Andrew Bailey will likely be non-tendered and Matt Thornton's option has already been declined.  Joel Hanrahan could be re-signed to a low-cost deal since the former closer missed almost all of 2013 after undergoing Tommy John surgery.

Between a surprise World Series win, their talented veteran core and the minor league system with the best short-term potential of any in baseball, these are heady times for the Red Sox.  It's probably too much to expect everything to again work out for the franchise in 2014, just as it was pessimistic to presume that things would continue to spiral downward following the disastrous 2012 season.  If the team does even as half as good a job filling their holes as they did last winter, however, expect more postseason action at Fenway Park.

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