It’s rare that a 100-win season can feel like a let-down, but when one’s chief division rival wins 108 games and captures a World Series title, the sentiment is more understandable. That’s the situation in which the Yankees find themselves, and they’ll likely act aggressively in an effort to close that gap this winter.

Guaranteed Contracts

Giancarlo Stanton , OF/DH: $270MM through 2027 (Stanton may opt out after 2020; if he does not, Marlins will pay $30MM of his remaining salary over the life of the contract)

, OF/DH: $270MM through 2027 (Stanton may opt out after 2020; if he does not, Marlins will pay $30MM of his remaining salary over the life of the contract) Jacoby Ellsbury , OF: $48.7MM through 2020

, OF: $48.7MM through 2020 Masahiro Tanaka , RHP: $45MM through 2020

, RHP: $45MM through 2020 Aroldis Chapman , LHP: $45MM through 2021 (Chapman may opt out after 2019)

, LHP: $45MM through 2021 (Chapman may opt out after 2019) CC Sabathia , LHP: $8MM through 2019

, LHP: $8MM through 2019 Brett Gardner, OF: $7.5MM through 2019

Arbitration-Eligible Players (service time in parentheses; salary projections via MLBTR contributor Matt Swartz)

Free Agents

[New York Yankees depth chart | New York Yankees payroll outlook]

Last offseason, much was made of the efforts by the Yankees (and several other big-market organizations) to dip below the $197MM luxury tax barrier (which rises to $206MM for the upcoming season). With mega-stars Bryce Harper and Manny Machado looming on the horizon, there was a belief in many instances that teams were preparing to make a run at one or both 26-year-old MVP-caliber talents. That may not have genuinely been true of all teams that endeavored to reset their tax penalty, but it does seem that there was some truth to that belief as pertains to the Yankees. They’ve already been connected to both and likely will continue to be until the pair has signed (be it in the Bronx or elsewhere).

Harper is a clumsier fit for the Yankees, who already are set to deploy an outfield mix including Aaron Judge, Giancarlo Stanton, Aaron Hicks, Brett Gardner and, if he’s healthy and still with the organization, Jacoby Ellsbury. Long-lauded prospect Clint Frazier, too, remains a consideration after an injury-marred 2018 campaign. Given that mix of outfielders, there’s no clear “need” for Harper, though as is always the case with this type of player, there will be multiple teams without an immediately clear “need” that are in the mix. In fact, that same perception applied to an extent last year when the Yankees acquired Giancarlo Stanton from the Marlins.

If the Yankees were to embark on a serious pursuit of Harper, there’d be multiple avenues to making the arrangement work. Harper could rotate through the corner outfield/DH spots with Stanton and Judge, with each seeing occasional time at DH in order to best remain healthy and fresh throughout the year. Agent Scott Boras has already pitched the idea that Harper could be a quality option at first base, though it doesn’t seem likely that the Yankees (or any other club) would simply plug him in as the everyday option there; perhaps he could get an occasional start at the position against tough righties to spell Luke Voit. The specifics behind a theoretical Harper-to-Yankees scenario are probably not all that worth dwelling on, as they seem likely to remain just that — theoretical. The fit is a bit messy, and while the Yankees won’t be entirely ruled out so long as he’s a free agent, they’re also unlikely to be portrayed as a significant favorite.

That’s less the case for Machado, whose fit in the Bronx became even clearer with the revelation that Didi Gregorius would require Tommy John surgery that’ll keep him out for much of the 2019 season. Depending on when medical experts project Gregorius to be able to return, it’s even possible that he’ll be non-tendered or signed to a different contract that lessens the burden of next season’s projected $12.4MM salary. His future is likely being debated among Yankees officials extensively, and without any specific insight into his exact recovery timeline, it’s tough to forecast exactly how (or if) he factors into the organizational plans. Gregorius is, after all, slated to become a free agent next winter.

Regardless of the return date for Gregorius, his injury opens a clear spot to play Machado at shortstop for the first few months of the 2019 season — and possibly beyond. Machado would give the Yankees a middle-of-the-order presence at a premium position, and while signing him would all but assure a return to luxury tax territory, the Yankees would be in the lowest penalty bracket thanks to last year’s financial machinations.

Concerns regarding Machado’s makeup abound following his October comments about his habitual lack of hustle and his likely deliberate clipping of Jesus Aguilar’s foot on a play at first base in the NLCS. Yankees managing partner Hal Steinbrenner has already declared that such antics “ain’t going to sell where we play baseball,” and emphasized the importance of the organization having a heart-to-heart discussion with Machado regarding his attitude. To be fair to Machado, while his “Johnny Hustle” and “not my cup of tea” comments reflect poorly, the latter half of his sentiments — the ones in which he said his lack of hustle “looks terrible” and is something he’s worked to change — have been largely ignored in favor of the more sordid portion of his interview. He clearly should have taken a more apologetic tone in the first place, but he’ll surely point to the second half of his comments when meeting with teams in an effort to curb the sting of his jarring comments. As for his actions against Aguilar, it’s unclear exactly how he could justify that behavior.

Looking strictly at the on-field fit, adding Machado would create some problems for the Yankees — at least on the defensive side of the equation. For all of rookie third baseman Miguel Andujar’s accolades at the plate, he rated as the worst defensive third baseman in the Majors this past season by measure of Defensive Runs Saved (-25), Ultimate Zone Rating (-16.0) and Revised Zone Rating (.634). Machado’s glovework at shortstop also checked in well below average, and while he made some improvements as the season wore on, the defensive pairing of Andujar and Machado on the left side of the infield would be lacking.

That dovetails, to an extent, with the Yankees’ need for rotation improvements. Andujar’s bat makes him a fan favorite in the Bronx, but there’s been plenty of speculation that he could also be used as a trade chip in order to acquire some rotation help. Machado could slide over to third base in that instance, with Gleyber Torres assuming his natural position at shortstop. That’d free the Yankees to peruse a deep slate of options at second base, where free-agent options would include Brian Dozier, DJ LeMahieu and Jed Lowrie, among others.

Including Andujar in a trade for rotation help is far from a given and is but one of many possibilities that Cashman and his staff figure to explore when looking to add to a group that is still unsettled even after re-signing CC Sabathia almost immediately after free agency began. Trade possibilities will be plentiful, with James Paxton, Zack Greinke, Robbie Ray and even Indians stars Corey Kluber, Carlos Carrasco and Trevor Bauer seeing their names surface in early offseason rumors. Free agency will have its options, too; Patrick Corbin heads up the free-agent market and has been connected to the Yankees for the better part of a season. Dallas Keuchel, J.A. Happ, Charlie Morton and Nathan Eovaldi are among the next tier of names that could be considered.

Of course, the Yankees have a trade candidate of their own on the roster at present. Sonny Gray’s time in Yankee pinstripes is all but finished, as Cashman as taken the somewhat uncommon approach of publicly declaring that a change of scenery is likely best for Gray. At least five clubs already have interest in Gray, who was generally excellent away from Yankee Stadium in 2018, so the Yankees should find a trade partner — perhaps even one willing to send something of modest 2019 value in return.

However things shake out with Gray, the Yankees seem likely to add multiple starting options this winter. Luis Severino, Masahiro Tanaka and Sabathia are currently penciled into the rotation, and while fans are anxiously anticipating the day when Justus Sheffield receives an earnest look as a starter, the team would be better served if Sheffield were able to be eased into the mix rather than thrown into the fire and counted on as a contributor from day one. Beyond Sheffield, names like Jonathan Loaisiga, Domingo German and Chance Adams can be viewed as depth options or possible bullpen pieces, depending on organizational preference.

On the subject of the bullpen, the Yankees already have an imposing group of relievers that could withstand the losses of both David Robertson and Zach Britton. Currently, the relief corps is anchored by Aroldis Chapman, Dellin Betances and Chad Green. Jonathan Holder made strong strides in 2018, as well, while Tommy Kahnle remains with the club as a high-upside option coming off a disastrous 2018 campaign. That’s a nice foundation to a strong ’pen, but there’s clearly room for the Yankees to add to the mix — with a possible emphasis on looking at options who throw from the left side. A reunion with either Robertson or Britton would certainly make sense, but there should be quality options at more affordable rates in free agency. The trade market, too, will feature myriad options as it does every offseason (as explored in MLBTR’s Market Snapshots for righty and lefty relievers).

As far as the Yankees’ lineup is concerned, there’s arguably only a true need for one significant upgrade — be it at shortstop to replace Gregorius for half the season or at second base in the event that Torres slides over to short in Sir Didi’s absence. Beyond the bevy of corner outfield options noted above, Aaron Hicks delivered a terrific all-around season in center and should be counted on as the primary option there. Voit’s Herculean showing in September may have earned him a legitimate look at first base, leaving Greg Bird behind as a leapfrogged depth option. Perhaps relying on a pair of players who are still largely unproven would be leaving too much to chance for the Yankees, however. If that’s the case, then there’s no reason they couldn’t make a legitimate run at perennial NL MVP candidate Paul Goldschmidt, for whom the D-backs are reportedly open to exploring trades. Goldschmidt is only a season away from reaching free agency, but would be a massive addition to the lineup and the rental scenario has its advantages as well. (He wouldn’t tie the organization’s hands in the long run and the club could anticipate recouping draft compensation through the qualifying offer system at season’s end.)

Gary Sanchez struggled through a miserable season at the plate, but he’s since undergone left shoulder surgery to address an issue that could certainly have impacted his swing. He’s expected to be ready for the start of Spring Training. I’d argue that the Yankees could be well-served to add a backup option with more offensive upside than Romine — particularly with Sanchez now recovering from surgery — but Cashman suggested last season that non-tendering Romine was never really a consideration. Romine, to his credit, showed more power than ever in 2018 and seemed to take a legitimate step forward with the bat — all while delivering solid defensive contributions.

Perhaps for the Yankees, then, the rest of the bench will be the primary area of focus once the middle-infield situation is sorted. Tyler Wade, Ronald Torreyes and recent waiver claim Hanser Alberto are among the top options for a utility infield role, but none brings much in the way of offense to the table. There’s arguably no great need for a player of Marwin Gonzalez’s caliber, but there’s also little denying that he’d strengthen the bench and give the Yankees the type of versatility that teams increasingly covet. While he’ll be substantially move expensive than Neil Walker was last winter, Gonzalez would fill the role Walker occupied much more capably for years to come. In theory, he could even be the Yankees’ primary infield addition if Machado lands elsewhere, as he’d be more than capable of starting at second base while Gregorius mends.

That’s likely too great a focus on one individual option, however — particularly one who’d fit on virtually any team in the league. Any of Lowrie, Asdrubal Cabrera or Josh Harrison could be fits in a semi-regular role before shifting to a utility capacity when the Yankees are at full strength. If the organizational preference is to simply find a strong defender to replace Gregorius in the early going, either Jose Iglesias or Freddy Galvis could fit that bill before moving into a utility role later on, though neither brings much offensive excitement to the table.

Generally speaking, the Yankees have the ability to spend at levels that far outpace their financial behavior in recent offseasons. New York has $156MM on the books in 2019 (including arbitration projections and pre-arb players) and would see that number dip to $147MM if and when Gray is traded. That’s a relative pittance for a club that has opened the season with a $200MM+ payroll eight times dating back to the 2008 season. And, taking a long-term look, the Yankees have just two contracts on the books as soon as 2021 — those of Stanton and Chapman, either of whom could technically opt out of their contracts before that point.

Viewed through that lens, the Yankees have the resources to be as bold as they like this offseason. The most straightforward approach could include something like signing Machado and Corbin while also trading for Paxton, and they’d have the financial means to not only do so with ease but to do so with the knowledge that such an aggressive slate of moves could come with just a single year of luxury tax penalties. That’s but one example of the manner in which the Yankees could operate this winter — and, likely, one that is too simplistic — but serves to underscore one bottom-line point: if they wish to do so, the Yankees are better-positioned than at any point in the past half decade to emulate the “Evil Empire” era with a hyper-aggressive series of offseason expenditures.