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The Red Sox jumped from the AL East basement in 2015 to first place in 2016, and they own one of the game’s most enviable collections of young talent. Despite all this progress, however, the season ended on the sour note of an ALDS sweep at the hands of the Indians. The Sox have to address some pitching questions, as well as try to replace the irreplaceable in franchise icon David Ortiz.

Guaranteed Contracts

Arbitration Eligible Players (service time in parentheses; projections via MLB Trade Rumors)

Free Agents

Boston Red Sox Depth Chart; Boston Red Sox Payroll Overview

Front office retooling has been the early story of Boston’s offseason. General manager Mike Hazen left the club to become the Diamondbacks’ new GM and executive vice-president, while Sox VP of amateur/international scouting Amiel Sawdaye also departed for Arizona to serve as Hazen’s assistant GM. Hazen isn’t being directly replaced, as assistant GMs Brian O’Halloran and (newly-promoted) Eddie Romero will essentially fill his role as the top lieutenants to president of baseball operations Dave Dombrowski.

Hazen and Sawdaye are very notable losses for the Sox, as the two executives played big roles in the team’s recent successes in scouting and player development. Ultimately, Dombrowski is still the one calling the shots in Boston, and the coming winter will indicate whether he feels the need to significantly alter or merely fine-tune what is already a strong roster.

The biggest absence, of course, is Ortiz, who will head into retirement after an incredible farewell season. At age 40 and playing despite severe lower-leg and foot injuries, Ortiz delivered one of his best seasons, hitting .315/.401/.620 with 38 homers and a league-best 48 doubles. Filling Ortiz’s role as a clubhouse and franchise leader was already an impossible task, yet replacing his production on the field will be almost as tall an order.

Early speculation has linked the Red Sox to free agent Edwin Encarnacion, one of the few bats on the open market capable of matching Ortiz’s slugging numbers. (Ortiz himself, somewhat controversially, has also suggested that the fellow Dominican is a good fit to replace him in Boston.) Encarnacion is also capable of playing first base, so he and Hanley Ramirez could share first and DH between them, locking down both positions with big power bats.

If the Sox aren’t willing to make such a big investment in years or dollars, then they could look beyond Encarnacion to the likes of Jose Bautista, Mark Trumbo, Kendrys Morales, Brandon Moss, Mike Napoli, Carlos Beltran or Matt Holliday. The latter two names on that list may not command more than a one-year deal, which Boston may prefer for flexibility’s sake given how the team is overflowing with position player options. Beltran and Morales are switch-hitters while Moss hits from the left side, in case Boston wants to prioritize replacing Ortiz with another left-handed bat.

The Red Sox have Ramirez playing every day at either first or DH and are further set in right field (Mookie Betts), center field (Jackie Bradley Jr.), second base (Dustin Pedroia) and shortstop (Xander Bogaerts). Rookie Andrew Benintendi has the inside track on the regular left field job after his impressive debut season. Veteran outfielder Chris Young is on hand to potentially platoon with Benintendi or at least spell him against some tough southpaws, though the Sox are hopeful that Benintendi can become yet another homegrown lineup staple.

Beyond these established positions, there’s quite a bit of uncertainty at third base and the other first base/DH spot, and those two problem areas could end up being tied together. WEEI.com’s Rob Bradford speculated that, if the Red Sox don’t acquire a first base/DH type at all, they could juggle Travis Shaw, Pablo Sandoval and Yoan Moncada between third, first and DH, with notable prospect Sam Travis also in the mix at first. Super-utilityman Brock Holt (who actually started Boston’s three postseason games at third) would presumably also be in the mix in this scenario.

The issue with this plan, of course, is that all of these players carry significant question marks. Shaw’s production faded considerably after a hot start, though he still provided good defense at the hot corner. Moncada, perhaps the game’s top prospect, struck out 12 times in 20 MLB plate appearances (admittedly a small sample size) and might not be quite ready for a significant role in the bigs. The highly-touted Travis missed much of 2016 after tearing his ACL. Sandoval is a total wild card, struggling badly in 2015 and missing almost all of 2016 due to shoulder surgery, though the club is reportedly happy with his recovery and improved conditioning. Given that the Red Sox chose Shaw over Sandoval in Spring Training last year, the Panda’s big contract won’t give him any advantage in the fight for playing time.

The simplest answer, then, could be to limit all these questions to third base and sign a player like Encarnacion to solidify the other first base/DH role. Looking at the problem from the other end, could the Red Sox sign a third baseman? This would be the less likely answer, as signing the likes of Justin Turner would block Moncada (whose athleticism would be wasted in a first base/DH role) or longer-term prospects like Rafael Devers. Luis Valbuena would be an intriguing addition, as he wouldn’t require more than a two- or three-year deal. He provides additional left-handed balance to Boston’s lineup, can play both third and first base, and Valbuena’s power seems like a nice fit for Fenway Park.

Catcher is another unsettled position for the Sox, though Sandy Leon’s out-of-nowhere production gave them an unexpected boost last year. Leon posted a whopping 1.074 OPS over his first 167 PA, but he came back to earth quite sharply over his last 116 PA (a .515 OPS). The Red Sox would be satisfied if Leon can hit halfway between those two extremes in 2017, though given his .392 BABIP last year, there’s more evidence indicating that Leon was simply on an extreme hot streak last summer than there is proof that he has really turned a corner at the plate.

Boston will go into the offseason with Leon as the starter and Christian Vazquez slated for the backup role, as the defensively-gifted Vazquez is still trying to find any sort of competency at the plate. The Red Sox have already declined their $3.75MM club option on Ryan Hanigan, buying the veteran backstop out for $800K. The team could try to re-sign Hanigan as minor league depth, though he may still be able to find a clearer path to big league playing time with another team, Hanigan’s injury-plagued season notwithstanding.

If the Sox wanted to make a big move behind the plate, they could explore signing Wilson Ramos, who will be out of action until roughly midseason due to right knee surgery. This injury hasn’t stopped Ramos’ agent from seeking four- or five-year contracts this winter, and the Sox are wealthy enough to perhaps risk of giving such a commitment to a player with a checkered health history. It’s hard to tell how Ramos’ market will develop in the wake of his ACL tear, though one would expect Boston to at least check in on what it would take to sign the catcher.

Former top prospect Blake Swihart was shifted to left field from behind the plate due to questions about his defense, though his development at the new position was cut short thanks to an ankle injury that eventually required surgery. Swihart appeared in just 48 total games between the majors and Triple-A in 2016, and he’s probably ticketed for more minor league seasoning to get him acclimated to left.

If Swihart doesn’t win a reserve job, then the Red Sox bench shapes up as Vazquez, Young and Holt, with rookie Marco Hernandez an interesting candidate due to his ability to play second, third and short. Boston could seek out a right-handed hitting utility infielder given that Hernandez, Holt, Shaw and Sandoval all hit from the left side, though the switch-hitting Moncada could be an internal answer. One would think, however, that the Sox wouldn’t have Moncada on the 25-man roster unless they could give him more playing time than a part-time role.

With so much position player depth at both the major league and minor league levels, it wouldn’t be surprising to see the Sox offer some of this depth in trade talks to acquire pitching, which looks like Boston’s most pressing need. Dombrowski has historically not been shy about dealing prospects for established MLB talent, and in his year-plus in charge of the Red Sox, Dombrowski has already shipped such highly-regarded prospects as Manuel Margot, Javier Guerra and Anderson Espinoza out of town in separate trades with the Padres for Craig Kimbrel and Drew Pomeranz (though it’s probably safe to assume that the Sox aren’t likely to be doing much more business with San Diego in the near future.)

Offering Moncada or Benintendi would open the door for the Red Sox in trade talks about virtually any semi-available starter in the game. Especially in the wake of the Pomeranz controversy, however, Dombrowski isn’t dealing one of his blue chip prospects unless he got a true ace back in return. If Benintendi is ready for the bigs and Moncada is close, however, Boston could be more open to dealing from its 25-man roster.

I’d imagine the Sox would be interested in dealing Sandoval if they could, even if it means taking on another bad contract or eating some money in the process. Swihart seems like a bit of an odd man out if he’s not going to catch and he’s blocked by Benintendi in left field, and Swihart would generate some solid interest as a post-hype prospect. Travis would also get interest, though the Red Sox would be selling low on an intriguing hitter prospect in the wake of Travis’ abbreviated 2016. Shaw is probably only a candidate to be moved if the Sox made another trade or acquisition to address third base, unless they were sold on Sandoval making a comeback or Moncada’s ability to handle MLB pitching.

None of the bench guys would net the Red Sox the frontline rotation help they’d be looking for, so could they instead move one of their lineup cornerstones? They had talks with the White Sox over the summer about Chris Sale and Jose Quintana, with Boston unwilling to give up Bradley to land either pitcher. Bradley is an immensely valuable asset — a 26-year-old elite center field glove with an emerging bat who is just entering his arbitration years. That said, Bradley has struggled to hit left-handed pitching and his hitting as a whole declined over the last two months of the season. If the Sox have any reservations about Bradley’s development as a hitter or are simply willing to bite the bullet to land an elite arm, he could be dealt, leaving Betts or Benintendi taking over in center field and left field becoming the province of a Young/Holt/Swihart platoon mix (or, the Sox could turn around to try to sign another outfielder).

A player like Bradley is a high price to pay, though that could be the going rate for pitching trades this winter given how the free agent starting market is incredibly thin. The Sox might not be too active in the open market when it comes to pitching upgrades aside from checking in on a reunion with Rich Hill. The veteran lefty revived his career in the Boston system in 2015 and went on to post tremendous numbers (when healthy) with the A’s and Dodgers this year. Given the issues at the back of Boston’s rotation, letting Hill depart last winter looks like a missed opportunity.

Rick Porcello and David Price have the top two rotation spots locked up, with Porcello delivering a career-best performance in 2016 while Price somewhat struggled by his lofty standards in his first year in a Red Sox uniform. Steven Wright, Eduardo Rodriguez, Clay Buchholz and Pomeranz are all in the mix for the other three rotation jobs, though all are dealing with either injury and/or consistency concerns heading into the winter.

Signing someone like Hill or adding another top-tier arm in a trade would go a long way towards solidifying the pitching staff. If a new pitcher is added and Wright, Rodriguez, Pomeranz and Buchholz end up all being healthy and productive, then that’s certainly a “problem” the Red Sox would love to face. In the (perhaps unlikely) event that the Sox face a pitching surplus, those starters could be traded or used in the bullpen. Buchholz drew interest when his name was floated at the deadline, or even the promising Rodriguez could be shopped to land a more proven major league talent.

The Red Sox got a pretty solid overall performance from their bullpen last year, though some changes are in the offing. Kimbrel’s first season in Boston saw him post career highs in ERA (3.40) and walk rate (5.09), though while he wasn’t the utterly dominant closer he was with the Braves, Kimbrel was still very effective. Robbie Ross, Joe Kelly, Matt Barnes and Heath Hembree will all return, and 2015-16 offseason addition Carson Smith should be back at some point later in the season after undergoing Tommy John surgery last May.

Even with this depth on hand, the Red Sox will hunt for more bullpen help in the form of another left-hander to pair with Ross (Fernando Abad was very ineffective after coming to Boston) and a setup man to set the table for Kimbrel. Free agents Koji Uehara and Brad Ziegler will both get consideration for that eighth-inning role, as the two veterans were quite effective last year. Uehara still posted strong peripherals despite a 3.45 ERA inflated by a spike in homers allowed, and he’ll likely be available on a one-year deal as he enters his age-42 season, while the Red Sox will need a multi-year commitment to retain Ziegler.

It isn’t out the question that Boston makes a surprise play for one of the top free agent closers on the market this winter in an effort to create its own version of an uber-bullpen, though I’d consider it to be a bit unlikely given the team’s other needs. Given how good Kelly looked after officially switching to a relief role last year (an 1.02 ERA and 21 strikeouts in 17 2/3 IP out of the pen), the Sox are hopeful that they already have one burgeoning weapon already on the roster.

There’s certainly potential for the Red Sox to go big to address their lineup or rotation needs, though the team has so much talent on board that Dombrowski can be flexible with his offseason dealings. One notable move (like, say, dealing Bradley) could trigger a chain reaction in Boston’s plans for 2017 and in the future in terms of freeing up positions for prospects, or potentially chasing established players this winter in free agency or trades. Dombrowski could also just as easily choose to only tinker with his roster until he knows exactly what he has in certain youngsters or underachieving/injured veterans. Some moves are certainly on the horizon for a Red Sox club that clearly feels it can contend for a World Series next year.