Clogged and committed, there are few ways for the Yankees to improve in 2026
The New York Yankees want to improve in 2026, but that may not be possible.
Not easily, at least, as years of pedal-to-the-metal procurement, spliced with reluctance to change, have left little room for manoeuvre.
Brooding after a 94-win season yielded a sixteenth straight fruitless October, aloof owner Hal Steinbrenner is sticking with stale general manager Brian Cashman, who is persisting with flawed manager Aaron Boone. Why? Because everyone gets a job for life, apparently, regardless of results.
With little top-down pressure and a surfeit of institutional stubbornness, Cashman and his obstinate minions face a complicated winter plagued by awkward roadblocks. Yes, there is almost $70 million coming off the books, as Cody Bellinger, Paul Goldschmidt and Devin Williams highlight a slew of expiring contracts. (1) But with a clogged roster containing too many similar players who do not complement each other, and a budget that is already uncomfortably large for Steinbrenner, there are few pathways to the kind of dramatic overhaul that is required to take the next step.
Already, the Yankees have extended the $22.025 million qualifying offer to outfielder Trent Grisham, who had a career year in 2025, clubbing 34 home runs while playing solid defence. Something of an afterthought who hit .191 in 381 games between 2022 and 2024, Grisham earned $5 million this season, and while he delivered tremendous value, dangling a 340.5% pay rise in front of a career backup seems shortsighted. Rooted in historic data, the odds of regression are huge, and allowing someone else to overpay for Grisham seemed like the easiest way of beginning to ease the Yankees’ logjam of lefty hitters – especially in the outfield.
With Aaron Judge ensconced in right field and Giancarlo Stanton marooned at DH, if Grisham accepts the qualifying offer and the Yankees bring back Bellinger, as most fans want, that would essentially recreate the 2025 outfield at a greatly inflated cost. Such a schematic would also consign Jasson Domínguez to a backup role while keeping Spencer Jones – the 6-foot-7 outfield prospect – in the minors. Those outcomes do not clarify the Yankees’ long-term roadmap, in my opinion, adding to the stultifying stasis.
Domínguez played 123 games in 2025 but lost reps to Grisham due to inconsistency. That said, The Martian is still only 22-years-old, and viewed through that prism, his .257 average, .331 OBP and 23 stolen bases in 2025 were cause for quiet optimism. Only nine players 22-or-younger accumulated at least 400 MLB plate appearances in 2025, and Domínguez ranked fourth among them in OBP. He is something of a butcher in the field, though, with -13.2 defensive WAR this season, and while nominally a switch-hitter, Domínguez hits far better from the left side, exacerbating the logjam. (2)
A similar status enshrouds Jones, a first round draft choice long mooted as a potential Judge heir. Jones has prodigious power, but eye-popping strikeout numbers have slowed his minor league progress. He seemed to finally put it all together this season, however, hitting 35 home runs to complement a .274 average, .362 OBP and .932 OPS across Double-A and Triple-A. Importantly, Jones will turn 25 in May, and he needs big league exposure – either with the Yankees or somebody else – right now. And as a fan of homegrown Yankee stars, I want that deserved opportunity to come in the Bronx.
In my mind, then, the starting point of this Yankee winter was deciding whether Domínguez and Jones will get a shot to play every day in 2o26. If so, Grisham and Bellinger could walk, to be replaced by a righty-hitting fourth outfielder. If not, move the Baby Bombers in another deal while bringing back Bellinger and a righty complement. The bottom line? There are too many lefty-hitting outfielders in the mix here, and Grisham probably has the least long-term upside, making the decision to give him the qualifying offer a clumsy one that begets further awkwardness.
I really like Bellinger, for what it is worth. He is a dynamic ballplayer who affects the game in myriad ways. In novel ways, by Yankee standards, too. He became a secret leader of the club this year while contributing 29 home runs, 25 doubles, 98 RBI and a 125 OPS+. However, there has been great variance in Bellinger’s career output –Rookie of the Year and MVP honours mixed with release by the Dodgers. Are the Yankees really going to commit to him for five or six years, at a nine-figure cost, when they have so many internal options to sieve through? Possibly not, I would suggest. And probably for the best, I would venture to argue. I would prefer to see Domínguez and Jones play themselves into irrelevance or stardom over the next half-decade.
The same logic applies to Kyle Tucker, yet another lefty-hitting outfielder, who sits atop most free agent power rankings. Yankee fans are clamouring for Tucker, and I get it – the guy has been an underrated superstar through eight big league seasons and, aged 28, is the rare free agent to hit the open market during his peak. There is a lot to like there, and Tucker would be a terrific Yankee, but I struggle to see Steinbrenner spending up to $400 million on an external lefty-swinging outfielder before first asking Cashman to reconcile Grisham, Bellinger, Domínguez and Jones – a big ask in a single offseason.
A similar conundrum lurks beyond the outfield, because the Yankees are lefty-heavy throughout their positional roster. Goldschmidt probably won’t return in 2o26 because the Yankees love Ben Rice, a lefty slugger, who has an inside track to the first base job. Meanwhile, Ryan McMahon, a lefty slugger, is under contract at third, and Jazz Chisholm Jr. – yes, a lefty slugger – is the incumbent at second. Behind the plate, Austin Wells – you guessed it, a lefty slugger – is similarly beloved by Yankee functionaries, while J.C. Escarra, his backup, also bats from the left side.
A typical front office would likely sort through these issues relatively quickly, moving on from underperforming assets. The Yankees do not have a typical front office, however. They have an arrogant front office that refuses to admit its own fallibility by cutting losses derived from past faulty evaluations. That’s why Wells will be the everyday catcher in 2026 despite hitting .219 with a .275 OBP this season. That’s why Rice will get the first base job without due consideration to external alternatives like Pete Alonso, Josh Naylor and Luis Arráez. That’s why Stanton will remain the DH, precluding a run at Kyle Schwarber, whose swing has always seemed readymade for Yankee Stadium.
Similarly, I have long admired Munetaka Murakami, the 25-year-old Tokyo Yakult Swallows slugger who was recently posted for MLB consideration. With 265 home runs in eight NPB seasons – including 56 in one campaign to break a cherished Sadaharu Oh record – the in-prime Murakami can be stashed at third or first base. Not for the Yankees, though. Not without serious surgery. An ideal fit to replenish the Yankees’ core and extend their window of contention, Murakami will only wear pinstripes in 2026 if one of Rice, McMahon or Stanton do not – and Cashman is unlikely to make that happen.
There is a vast chasm between Yankee fan idealism and Cashman pragmatism, you see, and that annoying paradox will frustrate this winter, as it does every winter. Take shortstop, for example. Most Yankee fans want to move on from Anthony Volpe following a down year in which he hit .212 and led the American League with 19 errors. Sports talk radio and hyperbolic podcasts are ablaze with talk of Bo Bichette as a possible free agent replacement, but any rational observer of this front office will nix such speculation out of hand. The same obduracy that puts Rice at first and Wells behind the plate will pencil Volpe in at shortstop. At a push, José Caballero might platoon with Volpe as a stopgap until George Lombard Jr. ascends as the next great Yankee darling. There is no point wasting your time looking at other possibilities.
Where can the Yankees improve, then, realistically? Well, terminating the doomed Three Lefty Catchers Experiment feels like a quick win, with Escarra replaced by a righty foil to Wells. J.T. Realmuto would be a great under-the-radar addition, while Christian Vázquez and Elías Díaz may also be in play. Do such changes move the needle a great deal, though? Probably not. The hump will remain impervious to such marginal manoeuvring.
As ever, there are some big bullpen arms available, and Cashman may double-down on dominant relievers with David Bednar, Camilo Doval and Fernando Cruz already under contract. In replacing Williams and Luke Weaver, the Yankees may go big, but if they have been great at anything during this prolonged title drought, it has been building bullpens – and even that has not paid off with a ring, adding to the despondency.
A similar vexation surrounds the starting rotation, which is loaded on paper but flawed in practice. Gerrit Cole and Carlos Rodón will start 2026 on the injured list, with midseason return dates unclear. Meanwhile, Max Fried – he of the eight-year, $218 million contract – flattered in the regular season to deceive in the playoffs during his maiden Yankee season, looking more like a number two or three starter than an ace befitting the pay-check.
I really like Luis Gil and Cam Schlittler, electric phenoms both, while Will Warren is a capable fifth starter. Factor in Clarke Schmidt, another Cashman favourite, and there is little room on the mound, either. Sure, pitchers always get injured, and harbouring nine starters hoping five of them are healthy at any one time is a prudent strategy. But depth is beholden to optionality, and barring an unlikely trade, any backend import will need to be happy transitioning to the bullpen – or the DFA scrapheap – if a logjam ensues next summer.
That probably eliminates the Yankees from the market for top free agent starters like Dylan Cease, Framber Valdez, Michael King and Tatsuya Imai, and probably precludes trades for available arms like Sandy Alcántara, Mitch Keller, Luis Castillo and MacKenzie Gore. More realistically, the Yankees will shop more sustainable options like Chris Bassitt, Zac Gallen, Patrick Corbin, Erick Fedde, Justin Verlander, Max Scherzer, Jordan Montgomery, Tomoyuki Sugano, Andrew Heaney and Brandon Woodruff. Any of those would be a good addition, but none of them will guarantee a parade down the Canyon of Heroes.
In general, Yankee fans pine for a major paradigm-altering move this winter, and I understand that sentiment. This is an $8.2 billion franchise defined by winning championships – the very thing it has not done for almost a generation. (3) There is always urgency for the Yankees to pursue the biggest and best superstars, and I endorse that doctrine theoretically. This year, however, I just do not see a clear pathway to such a splashy transformation. Everywhere Cashman turns in pursuit of such upgrades, he wheel-spins in a cul-de-sac of his own creation.
Tarik Skubal would be a genuine game-changer, but talk of the Tigers trading him is overblown. Likewise, Paul Skenes in pinstripes would be an era-defining dream, but why would Pittsburgh dump the greatest pitcher of his generation? I have similar daydreams about Fernando Tatís Jr. and perhaps even Steve Kwan, but I just do not feel Cashman is ready to go for the jugular with such a move. The days of him swooping in to land someone like Alex Rodriguez just because he could are long gone, unfortunately. The Dodgers have assumed that mantle, and the Yankees are far more reticent these days.
Ultimately, Cashman has backed himself into a corner. Rodriguez himself said as much recently while broadcasting for Fox during the postseason. “One of the worst constructions of a roster I’ve ever seen,” said A-Rod when asked to comment on the Yankees’ woes. “You have three left-handed catchers. You have five DHs. You have a first baseman in and out. It is just a very, very difficult hand for Boone. And honestly, they were exposed against a much better Jays team.” (4)
Once the poster boy for Yankee exceptionalism, a totem of bygone Steinbrennian imperialism, A-Rod is now a figurehead of the Bronx resistance, a leading voice in the collective forlorn lament of pinstriped entropy. I concur with Alex’s assessment, and the poor roster construction of which he speaks cannot be easily unpicked. Not without multiple moves and a rekindling of the values that once made the Yankees indomitable.
Cashman’s recent track record does not inspire confidence that such a radical shift is coming, however. The Yankees are mired in ideological stasis, an acceptance of glorious failure – ‘win enough to sellout a few playoff dates’ replacing ‘win at all costs’ as the benchmark for success – ingrained from Hal on down. As such, and though it contradicts decades of Yankee dogma, a case can be made for sitting out – or, perhaps more accurately, taking a breath – this winter. Even the Yankees need to come up for air periodically, and 2026 may provide an efficient opportunity.
If I were in charge, Domínguez and Jones would join Judge in the everyday outfield. Someone like Randal Grichuk or Harrison Bader would be signed as a backup. Realmuto would replace Escarra. And one of Stanton, Rice or McMahon would be jettisoned to accommodate a serious run at Murakami. I would move on from Goldschmidt, Bellinger and Grisham while adding a depth starter – Gallen or Corbin, most probably – and retooling the bullpen.
To some, that may resemble the waving of a white flag, or the taking of a big step back with veteran dependability sacrificed for youthful volatility. That is perhaps a fair critique, but it is also a gamble I’m willing to take because it would produce a more balanced, organic and future-focused roster. Not necessarily a better roster, year-on-year, but a roster that would finally answer some nagging questions – on Domínguez and Jones, primarily – that currently cloud the Yankee horizon. And that, to me, would be more interesting to watch, regardless of win-loss record, than running it back with largely the same team that just failed to win it all.
We all know that won’t happen, though. Precedent tells us Grisham and Bellinger will probably come back. Rice might continue to flourish into a solid slugger, admittedly, while Schmidt or Warren might be packaged for an upgrade like Alcántara. Few other pieces are likely to be shipped, however, leaving Domínguez and Jones in purgatory while the 2026 Yankees win 90 games again only to burn out fast in the playoffs with their long-term roadmap as murky as ever. I want to alter that predictable pattern and adjust that mind-numbing malaise, hence my advocacy of a soft reset, clarifying internal options before considering external alternatives.
The biggest argument against such a reset, and why it probably will not happen, is the waning primes of Judge and Cole. A case can be made to go all-in for 2026, building around that title-hungry duo, but – again – the avenues to that end are few and narrow. A possible player lockout and labour strife looms in 2027, and those prime years may be history by 2028, when Judge will be 36 and Cole 38. Ultimately, the greatest chance of a pinstriped championship may have passed for Judge and Cole, and the era they defined may be ending – no matter how difficult that is to admit.
In theory, a 2026 big league team with Grisham, Bellinger and McMahon playing every day will probably be better than one with Domínguez, Jones and Murakami, but that is far from guaranteed. All six players have documented inconsistencies, and predicting exactly what they will produce from one year to the next is notoriously difficult. What we do know is that a big league team with Grisham, Bellinger and McMahon failed to win the World Series in 2025. And that is an all too familiar outcome for an all too familiar algorithm.
Pragmatically, then, attention may soon turn to the next Yankee core. Lombard Jr. is widely earmarked for a 2027 debut – or a year later, if that season is wiped out by collective bargaining squabbles. Utopian projections add Jones, Domínguez, Gil and Schlittler to that envisaged nucleus. Skubal is a free agent after the 2026 season, too, with Skenes following in 2029. They are the next two era-defining jewels the Yankees must prioritise, existentially, and planning to accommodate them – financially and culturally – must begin now.
The most ardent advocates of pinstriped exceptionalism contend that the Yankees should never have to ‘save up’ for any player. Not with yearly revenues exceeding $700 million, at least. (3) The Evil Empire should pursue Bellinger and Tucker, Skenes and Skubal, Bichette and King, traditionalists bark. I broadly agree, but as average annual values for superstars spiral towards and beyond $50 million, there are only so many big-ticket items any team – even the Yankees – can shoehorn within a sensible pay scheme.
For luxury tax purposes, the Yankees have already committed $40 million per year to Judge through 2031; $36 million per year to Cole through 2028; $27.25 million per year to Fried through 2032; and $27 million per year to Rodón through 2028. They cannot keep doubling-down on those big bets year after year. Not without making the roster top-heavier than it already is. (5)
Accounting roughly for arbitration rises, the Yankees already have a projected payroll around $240 million in 2026 – before any of their own free agents return. (5) The first luxury tax threshold is set at $244 million for 2026, and thanks to four straight years exceeding that redline, Steinbrenner is all but assured a 50% penalty on every dollar spent beyond that. A further 60% surcharge will accompany any expenditure above $3o4 million. And while raising such concerns is often conflated with billionaire-loving sycophancy, those are real restraints that deter teams from repeatedly stacking chips while accentuating the virtues of fiscal sustainability.
To hone a more balanced roster, mitigate clubhouse tension born of pay inequality, and stay within a reasonable distance of the luxury tax threshold – say, $260 million – a team can probably afford to harbour three or four such mega-deals with AAVs around $30 million. That is why those cornerstone, era-defining players need to be ‘saved’ for, in some sense. Not necessarily because a team wants to pocket profits, but more because it wants to prolong its window of contention by staggering the costly declines of post-prime veterans.
Looking ahead, maybe the Yankees rearrange things and go get Tucker. Perhaps they move some combination of Rice, Wells, Domínguez, Jones, McMahon and Chisholm Jr. to open further routes to immediate improvement. A blockbuster trade might come out of nowhere, landing Skenes, Skubal or Tatís Jr. I just doubt it, however, because none of those approaches are consistent with how this regime has operated since the late-2000s.
Ultimately, then, I find myself swathed in apathy entering yet another Cashman offseason. I’m usually obsessed with the baseball hot stove, but years of frustration and disappointment have knocked the stuffing out of me. Even when obvious, ample solutions stare them in the face, the Yankees stick to their own stubborn path, so there is little hope for real change when potential fixes are scarce. I will probably take a step back myself, accordingly, and await the Opening Day roster with a sanity-preserving detachment. That way, the inevitable cannot aggravate me.
Sources
1. Kirschner, Chris. The Athletic. [Online] October 20, 2025. https://www.nytimes.com/athletic/6731439/2025/10/20/yankees-2026-payroll-offseason-trades-signings/.
2. Fangraphs. [Online] https://www.fangraphs.com/.
3. Forbes. [Online] https://www.forbes.com/teams/new-york-yankees/.
4. Morik, Ryan. Fox News. [Online] October 9, 2025. https://www.foxnews.com/sports/alex-rodriguez-calls-yankees-roster-construction-one-worst-hes-ever-seen-after-playoff-elimination.
5. Spotrac. [Online] https://www.spotrac.com/.