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After celebrating their fourth World Series in 15 years, the Red Sox now have some significant holes to fill in the starting rotation and bullpen. They’ll also need to think about whether and how to keep their championship core together for the long term.

Guaranteed Contracts

Obligations To Former Players

Pablo Sandoval, 3B: $23MM through 2019 (includes $5MM buyout of 2020 club option), minus prorated MLB minimum salary earned by Sandoval next season

Arbitration Eligible Players (service time in brackets; projections via MLBTR contributor Matt Swartz)

Free Agents

[Boston Red Sox offseason page][Boston Red Sox payroll information]

The Red Sox won 108 regular season games and then lost just three postseason contests en route to the Commissioner’s Trophy. The good news doesn’t end there for Boston fans, as the window is still wide open for another title. Potential AL MVP Mookie Betts and Hank Aaron Award-winning slugger J.D. Martinez are the cornerstones of a dynamic lineup that will also have Xander Bogaerts, Andrew Benintendi, and Jackie Bradley Jr. as Opening Day locks. Chris Sale, David Price, and Rick Porcello sit atop the rotation, with bullpen workhorses Matt Barnes, Heath Hembree, Ryan Brasier, and Hector Velazquez all returning.

That’s an awfully strong nucleus to start from, particularly for a team that can still account for less-stable positions with players already on the roster, and isn’t shy about making big trades or signings if external help is required. The Red Sox soared over the luxury tax threshold last season and are projected to be well over the line again in 2019, though they’ll get some help in that area by the fact that the luxury tax limit will rise from $197MM to $206MM. Hanley Ramirez’s salary is also now completely off the books; the $22MM he had earned annually will be needed to cover projected arbitration raises.

So, what will president of baseball operations Dave Dombrowski do for an encore? His most immediate question is the bullpen, as closer Craig Kimbrel and setup man Joe Kelly are both headed for free agency. The hard-throwing Kelly has had his ups and downs in Boston, with a 4.33 ERA over 359 1/3 innings for the team and persistent control issues. When Kelly was on, however, he was hard to touch — over 11 1/3 IP during Boston’s World Series run, the right-hander allowed just one earned run while recording 13 strikeouts and no walks. It’s easy to see how a rival team could take a chance on Kelly as a closer or top setup option, and offer him a contract beyond what the Sox are willing to pay. Then again, there’s still a fit on paper in Boston, so it’s possible he’ll return.

Meanwhile, Boston may only have limited interest in bringing Kimbrel back.After Aroldis Chapman and Kenley Jansen raised the bar on contracts for top closers, it could be that the Red Sox simply aren’t keen on spending the big money it will likely take to retain Kimbrel (MLBTR projects him for a four-year, $70MM contract). The Red Sox also stand to recoup a compensatory draft pick via the qualifying offer if Kimbrel signs elsewhere. Kimbral had another strong regular season — 2.74 ERA, 3.10 K/BB rate, 13.9 K/9 over 62 1/3 innings — yet didn’t quite hit elite levels, and he struggled mightily throughout the postseason.

If Kimbrel does leave, the Sox don’t have an obvious in-house saves candidate ready to step up to the unique pressure of Fenway Park in the ninth inning. Free agents like David Robertson, Zach Britton, or Andrew Miller could all be targets, or Boston could pursue trade options. This is assuming, of course, that the Red Sox will take a traditional approach to the closer role, as the club could prefer to add a versatile multi-inning arm (like a Miller) or two and then give manager Alex Cora a chance to mix and match his late-game options based on matchups.

Beyond the top three in the rotation, the combination of Eduardo Rodriguez, Brian Johnson, swingman Velazquez, and (health permitting) Steven Wright should be capable of accounting for at least one of the other rotation spots. This depth also comes in handy should Sale again run into any health issues, as Boston put a priority on keeping their ace as fit as possible for October. The Red Sox will likely add to this mix with at least one more starting arm. The team has the resources to check in on any of the top pitchers available on the free agent or trade markets, with a pursuit of Nathan Eovaldi standing out as a logical option. Eovaldi will still just be 29 on Opening Day, and looked as good during his two-plus months with the Red Sox as he has at any point in his career, both results-wise and in terms of his 97.2mph average fastball speed.

If not Eovaldi, Boston could look at other pitchers that could be longer-term answers for the rotation since both Sale and Porcello are entering the last year of their contracts. As good as the present looks for the Red Sox, Dombrowski will have to turn an eye to the future this offseason as several important players are approaching free agency. Sale, Porcello, and Bogaerts are all only controlled through 2019; Betts and Bradley will reach the open market after 2020; and Martinez can opt out of his contract after any of the next three seasons.

There have already been indications that Bogaerts and Martinez will test free agency, though the team will likely at least consider broaching extension talks with all of these parties. It will be interesting to see which players the Red Sox prioritize in negotiations, as it will provide significant information about their approach for the future. Bogaerts, Martinez, and Bradley are all represented by Scott Boras, whose clients tend to reach the open market rather than sign extensions. Sale has been nothing short of outstanding during his nine-year career, though with his lingering injury concerns, are the Red Sox prepared to make an expensive commitment to the southpaw as he enters his 30s? Could Boston also look to a different type of extension, and lock up a controllable player like Benintendi (scheduled for free agency after 2022) to a even longer-term deal?

Betts has preferred to take a year-to-year approach rather than sign an extension, a gamble that has thus far handsomely paid off for the superstar outfielder. Could his stance change if the Red Sox were to approach him with one of the biggest contracts in baseball history? The argument can certainly be made that Betts is deserving of such a pact based on what he has done through his age-25 season, and the Sox could get some obvious contact comps this winter in whatever record-breaking deals Bryce Harper and Manny Machado (both of whom are 26 themselves) find in the free agent market this winter.

The Sox are set in the outfield, DH, and shortstop, and we can pretty safely pencil Rafael Devers at third base and Mitch Moreland for a timeshare at first base next season. Despite below-average overall hitting numbers and a shaky glove in 2018, Devers is still only 22, and the former top prospect will certainly be given plenty of opportunity to break out. Moreland will continue to provide his solid defense and bat from the left side of the plate, though the Sox will need to find another right-handed first base as a platoon partner.

World Series MVP Steve Pearce filled that role in spectacular fashion after coming to Boston in midseason, and while his price tag may go up, the free agent market has been unfriendly enough to veteran first basemen in recent years that a re-signing is certainly feasible from Boston’s end. For Pearce, he may also welcome another crack at a ring rather than aim for a few extra dollars in free agency.

Could the Red Sox make a bigger splash at first base? That’s what we thought could be in store last winter before the team re-signed Moreland to a two-year contract, so Boston seems content for now to just stick with a platoon situation rather than deal Moreland and then pursue a bigger name in free agency or on the trade market. There’s also the possibility that the Sox might not want to block the position in the event that Devers needs to be moved to first base, as star prospect Michael Chavis is knocking on the door as a potential third baseman of the future. (Chavis himself has also seen some time at first base, plus young first baseman Sam Travis is still in the picture, albeit in need of a rebound from a lackluster Triple-A season.) All that said, there are some intriguing potential options and a move can’t be ruled out.

Catcher is another position where the team could theoretically stand pat with in-house options, as the duo of Christian Vazquez and Sandy Leon each posted outstanding framing numbers and were widely praised for their game-calling abilities. The Sox have enough big bats in the lineup that they could afford to devote one position entirely to defense, yet the near-total lack of offense generated by both Vazquez (42 wRC+) and Leon (33 wRC+) begs to be addressed in some fashion. Blake Swihart also contributed little at the plate while seeing some action at catcher as part of his super-utility duties.

The boldest move would be a trade for J.T. Realmuto, who will be targeted by every team in need of catching upgrades this winter. Vazquez or Swihart could go back to the Marlins as part of a trade package, though obviously Boston would need much more to pry Realmuto out of Miami. If the Red Sox aren’t willing or able to meet the Marlins’ price, they could aim lower by signing a free agent backstop like Kurt Suzuki or Robinson Chirinos or by taking over part of the contract of a pricey veteran such as Russell Martin. This would allow Vazquez to stay in the mix. The Sox have committed to him to some extent as their catcher of the future via their three-year contract extension, and Vazquez did post decent hitting numbers just in 2017. It remains to be seen exactly what the Sox will do with Swihart, who was kept despite a flurry of trade rumors last season, and whose stock has dropped even further after a forgettable 2018 season.

The experiment with Swihart as a utilityman led him to appear as one of the nine Red Sox players who played at least one game at second base last season, as the position became a revolving door thanks to Dustin Pedroia’s recurring knee problems. The longtime face of the Boston franchise was limited to just three games last season, leading the Sox to rotate several players through the keystone before Ian Kinsler was acquired at the deadline to solidify the position, though Kinsler didn’t play particularly well.

It’s an open question as to how much Pedroia will be able to contribute next season, especially since Dombrowski isn’t yet certain if the veteran infielder will be ready for Spring Training. Given Pedroia’s status within the organization (and the $40MM still owed to him through 2021), the Sox may have to hold off on any moves to address second base until they get more clarity on Pedroia’s health. If Pedroia isn’t an option, another in-season trade is likely, unless incumbent options Eduardo Nunez, Brock Holt, or maybe even longer-shot candidates like Chavis or even Swihart can all combine to handle the position.

A reasonably healthy and productive Pedroia, a step forward from Devers, and Vazquez returning to even his 2017 form would go a long way towards firming up three positions that were rather glaringly weak links last season. Even while receiving sub-replacement level production at second base, third base, and catcher all season, the 2018 Red Sox were still one of the best teams in recent baseball history. It’s a tribute to Cora’s work in the dugout and Dombrowski’s roster-building that Boston achieved what it did even with some notable flaws, and with another winter to address these areas and others, the possibility exists that next year’s Red Sox could be even better.