The Red Sox got an early start on their rebuilding for 2015, and their offseason efforts will focus on sorting through their outfield surplus and adding arms to both the rotation and the bullpen.

Guaranteed Contracts

Arbitration Eligible Players (service time in parentheses; projections via Matt Swartz)

Contract Options

Free Agents

Other Payroll Obligations

With a sub-.500 record and virtually no hope of a late-season run, the Red Sox decided to become July deadline sellers.  Most teams usually trade established players for prospects at the deadline, and the Sox didn’t shy away from this strategy themselves, adding young arms Edwin Escobar, Heath Hembree and Eduardo Rodriguez in separate deals for Jake Peavy and Andrew Miller, respectively.  Boston’s biggest moves, however, saw the team pick up pieces who can help them in 2015 — Yoenis Cespedes came from Oakland in exchange for Jon Lester and Jonny Gomes, while the deal of John Lackey to St. Louis brought back Joe Kelly and Allen Craig.  It was a nice return on two pending free agents (Lester and Peavy) and Lackey, who was contracted through 2015.

Kelly, who is controllable through the 2018 season, pitched decently in 10 starts after the trade and will join Clay Buchholz as the only locks for the 2015 rotation.  The Sox will hope that at least one of their young starters (Rubby De La Rosa, Allen Webster, Brandon Workman or Anthony Ranaudo) can win a rotation spot and provide solid innings next year, though given how this quartet struggled last season, Boston isn’t counting on anything.  Other prospects like Rodriguez, Henry Owens or Matt Barnes could be in the mix as well with a big Spring Training.

It remains to be seen if the Red Sox will pursue two new starters to fill the other two rotation spots, or if they’ll rely on internal options for one spot and then go for an ace.  It seems likely the Sox will bid on Kenta Maeda if the Japanese right-hander is posted, so he could account for one slot.  If the Red Sox look for a more proven ace, the biggest names on the free agent market are Max Scherzer, James Shields and ex-Boston playoff hero Lester; all will command big salaries, but team chairman Tom Werner recently said that the Sox are more than able to spend this offseason.

It still seems remarkable that Lester and the Sox couldn’t negotiate an extension, given that both sides were eager to work something out and Lester even indicated last January that he’d be open to taking a discount to remain in Boston.  He didn’t quite mean a discount in the form of a four-year, $70MM contract akin to the initial offer made the Sox during offseason negotiations, and it seems talks never quite recovered from that below-market offer.  It’s very possible that $70MM won’t even end up being half of what Lester receives in free agency.

While Lester could still re-sign with the Red Sox, it’s almost unheard of for a top-tier free agent to be dealt by his team at midseason and then rejoin them in the offseason.  Second of all, Boston’s uneasiness about guaranteeing long-term deals to pitchers in their 30s informed their initial offer to Lester in the first place, so it would be odd to see them reverse course now that they’re competing against others for Lester’s services.

One possible alternative could be Shields, who will be 33 years old on Opening Day (two years older than Lester) but more of a fit for the Sox since he could be open to a four-year deal, whereas Lester would want a six- or seven-year commitment.  The Red Sox have been scouting Shields already and seem like one of many teams who will be in the mix for “Big Game James.”  With a top-ten (seventh overall) protected pick in the 2015 draft, Boston will be free to pursue qualifying offer free agents while still hanging onto their first-rounder. (They would still, of course, need to forfeit their second-round selection.)

There’s also the possibility that the Sox could trade for an ace and move some of their prospect depth.  The Red Sox still have one of baseball’s most well-regarded farm systems, though the club will be a lot more careful about giving their prospects everyday roles in 2015.  Boston went into last season counting on Xander Bogaerts, Jackie Bradley and Will Middlebrooks to step up as lineup regulars, and yet all three badly struggled at the plate, with Bradley and Middlebrooks losing their everyday jobs by season’s end.

Middlebrooks in particular could be on the outs given that he declined to play winter ball, leading to some “disappointment” within the organization according to team president Larry Lucchino.  Whether Middlebrooks stays or goes, the Sox will be looking for a left-handed hitting third baseman (as Lucchino noted), and Brock Holt could be an internal fit, though he’s a middle infielder by trade.  The team could afford to use the versatile Holt mostly at third (or in a platoon with Middlebrooks) as Mookie Betts could take over the utility role.

For external options, a top-tier free agent third baseman like Pablo Sandoval would be a huge upgrade, or the Sox could pursue a trade for someone like the Pirates’ Pedro Alvarez, as the Boston Herald’s John Tomase recently speculated.  I’d also toss the Cubs’ Luis Valbuena into the mix as a trade candidate; Valbuena is coming off a quietly impressive season and has two years of control left, though he doesn’t have a long-term spot in Chicago thanks to all of the Cubs’ blue chip infield prospects.

Boston will be looking for left-handed bats in general, as improved lineup balance is a stated winter goal of GM Ben Cherington.  David Ortiz is the only left-handed hitter in an everyday role for the projected 2015 lineup, as Mike Napoli, Dustin Pedroia, Bogaerts, Christian Vazquez and all the outfielders (save Bradley and switch-hitting Daniel Nava) swing from the right side.  A new lefty bat could be slotted at third base, or in a platoon with Vazquez, or the Sox could explore trading two of their right-handed hitting outfielders for one left-handed hitting outfielder.

However it breaks down, the Sox certainly have to do something to finalize their outfield alignment.  The only outfielder seemingly guaranteed of a starting job next season is the one with the least Major League experience; Rusney Castillo posted an impressive .928 OPS in 40 PA in September, and Boston certainly expects him to see regular work given his seven-year, $72.5MM contract.  Castillo’s best position is center field, however, so now Betts could be blocked in both center field and by Pedroia at his natural position of second base.  There’s also Bradley, who entered the year as one of the game’s top prospects and delivered Glove Glove-caliber defense in center, despite looking completely overmatched swinging the bat.

With Castillo, Betts and Bradley in center, Cespedes and Nava in left, and Craig and Shane Victorino in right, at least one move is sorely needed to clear some room.  The other issue is that several of these players could be hard to trade since they’re coming off down years — Bradley, Nava and Craig all struggled while Victorino spent most of the season on the DL.  While Cespedes seems to be a great fit for Fenway Park, he isn’t yet sure if he wants to sign an extension in Boston, which could make him a trade candidate to be moved for pitching.

This is just my speculation, but Cincinnati and Philadelphia stand out as teams that could be natural trade partners for the Red Sox this winter.  The Reds have a hole in left field and seem destined to trade at least one of four starting pitchers entering their walk years.  Johnny Cueto or Mat Latos would provide a nice front-of-the-rotation boost for the Sox, though it’ll take more than prospects to acquire either pitcher (especially Cueto) since the Reds plan to contend in 2015.  Cincinnati could ask for an experienced, controllable youngster like Bogaerts or Betts in any negotiation, along with perhaps another MLB-ready piece like Nava (who has the on-base skills that the Reds are looking for — at least against right-handers) and/or a young pitcher.

The Phillies, meanwhile, would go in the opposite direction and ask for multiple top prospects in exchange for Cole Hamels as they attempt to rebuild their farm system.  Boston has the financial resources to pay the $96MM owed to Hamels through 2018 and they’d only be committed to Hamels through his age-34 season. It might take both fully absorbing Hamels’ contract and giving up a heavy prospect load to convince the Phils to make a trade, however, so the Sox might prefer to just spend on a free agent ace and keep their minor leaguers.

The bullpen also stands out as an area of great uncertainty for the Red Sox, starting with Koji Uehara‘s free agency.  Up until mid-August, Uehara was pitching so well that there was talk of extending him a qualifying offer (a one-year deal in the $15MM range), yet those discussions vanished after Uehara posted an 11.74 ERA over his final 7 2/3 IP of the season.  This doesn’t suddenly mean Uehara is finished, of course, as some regression was probably inevitable given the otherworldly numbers he posted in 2013 and in the first three-quarters of the 2014 season.  The Sox still have an interest in re-signing Uehara, and it’ll be intriguing to see how his market develops as teams weigh his late struggles and age against his pre-August superstar numbers.

As for the rest of the bullpen, it’s possible the young starters that don’t make the rotation could be used in relief roles, which would shorten Boston’s offseason shopping list.  Manager John Farrell would like to see free agent Burke Badenhop return, while Craig Breslow‘s $4MM team option seems likely to be bought out given his struggles in 2014.  Veterans Junichi Tazawa and Edward Mujica are still in the fold and rookie knuckleballer Steven Wright pitched well in limited action.  I’d expect the Red Sox to add at least one more experienced relief arm to the mix.  If Uehara departs, that experienced arm could well be a closer, either in a trade or as a free agent signing.

Miller has openly discussed how much he and his wife enjoyed their time in Boston, so it’s quite possible the Red Sox could look to bring back the southpaw.  His terrific season is only raising his price tag, though, and Boston may not want to pay the rumored rate of three years/$21MM for a setup man, even as one as dominant as Miller.  One potential solution could be for the Sox to sign Miller and then use him as a closer; while he’s never served as a ninth-inning man before, Miller has the classic high-strikeout rate and power arm that traditionally fits the closer mold.

The 2012-14 Red Sox became the first franchise to ever go from last place to a World Series championship to last again over a three-season stretch.  It’s been quite a roller coaster stretch for Boston fans, though they can take heart in the fact that recent history has shown their team could be back in contention very quickly.  Cherington and company have a lot of work to do this winter in sorting through both the young and veteran options on the roster, but with at least $50MM (hat tip to WEEI.com’s Alex Speier) in available payroll space to work with this offseason, the Sox are willing to spend to enable another quick rise up the AL East standings.

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