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What went wrong for the 2026 Yankees? And where do they go from here?

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For the third year in a row, the New York Yankees ended their season by watching an opponent celebrate on the Yankee Stadium grass in October. 

On Wednesday, it was the Tampa Bay Rays’ turn to do the honors after sweeping New York out of the playoffs, following the Toronto Blue Jays’ dominant effort in last year’s ALDS and the Los Angeles Dodgers’ wrapping things up in five games in the 2025 World Series.

In the ALDS sweep by Tampa, the Yankees’ pitching staff generally did its job, just as it had all season. But without Aaron Judge, sidelined due to a calf strain suffered in late September, the Yankees’ offense reverted to the worst version of itself — the version that was on display sans Judge for much of the regular season. Only Ben Rice looked remotely locked in, with the rest of the hitters showing minimal resistance to Tampa Bay’s army of arms, who flummoxed New York’s bats no matter how manager Aaron Boone arranged the lineup. The Yankees struck out 31 times and mustered just 12 hits across the three games, the lowest total in a multigame postseason series in franchise history.

The end of Game 3 was a fitting finale for the “run-it-back” Yankees, a not-so-flattering moniker ascribed after New York spent last offseason going to great lengths to keep its roster largely intact despite the early postseason exit at the hands of Toronto. Last winter featured the retention of outfielder Trent Grisham via the qualifying offer, the re-signing of key role players Amed Rosario and Paul Goldschmidt, plus relievers Paul Blackburn and Ryan Yarbrough, and a massive new contract for outfielder Cody Bellinger — all while making minimal upgrades beyond the returnees.

Across the regular season, some holdovers performed better than others. Blackburn excelled in relief, exemplifying New York’s developmental competence and ingenuity on the mound. The veteran Goldschmidt raked in the first half but faded badly down the stretch. Bellinger shined all summer but was a nonfactor against Tampa Bay, going 1-for-12. And after an underwhelming regular season, it was Grisham who represented the Yankees’ last hope in the ninth inning of Game 3, having been inserted into the leadoff spot as a last-gasp lineup shake-up from Boone, with hope that his plate discipline could show up when his team needed him most. Instead, with the tying run on second base, Grisham struck out on four pitches, leaving Rice on deck and punctuating an 0-for-5 with three strikeouts. 

Fair or not, the optics of the final at-bat of the 2026 Yankees’ season make it tough to believe that running it back was ever going to be a recipe for success. Now New York once again begins its offseason in early October with a chance to enact significant change. Early reports indicate that neither general manager Brian Cashman nor manager Aaron Boone is at risk of losing his job, so the roster will be the focus.

TrentGrisham
CF – NYY – #12
JazzChisholm Jr.
2B – NYY – #13
TrentGrisham
CF – NYY – #12
JazzChisholm Jr.
2B – NYY – #13
2026 season

418
AB
471
.211
AVG
.231
18
HR
19
9
SB
41
.703
OPS
.711

Will they shake things up to a meaningful degree? Grisham is one of several key Yankees scheduled to hit free agency, and he appears the least likely to stick around, especially given the emergence of outfielder Spencer Jones. Joining Grisham on the open market will be second baseman Jazz Chisholm Jr. and closer David Bednar, each of whom could command a significant sum in a notably weak free-agent class. Bednar was a brilliant fit at the backend of Boone’s bullpen this year, but the Yankees have proven capable of covering high-leverage innings without paying top dollar. They let Devin Williams and Luke Weaver depart in free agency last year; will they do the same with Bednar? 

Chisholm’s fit with New York moving forward is more complicated. The Yankees’ infield is both completely unsettled and awfully crowded. Is George Lombard Jr. a lock to be the Opening Day shortstop? Could Anthony Volpe be the every-day second or third baseman, or should he be in a bench role? Does Ryan McMahon, still owed $16 million next season, have a place on this roster? And what about midseason addition Luis Garcia Jr. — could he return to his native second base, despite his poor defensive reputation? 

And that’s just the infield. Giancarlo Stanton has a year remaining on his contract, but his durability is tenuous to say the least, and the DH spot will already be occupied by the likes of Garcia, Rice and perhaps Judge.

As they look to 2027, the Yankees can at least take solace in the knowledge that their pitching staff is in sterling shape, with an excellent (albeit expensive) rotation headlined by an ascendent homegrown ace in Cam Schlittler. Still, there is much to be resolved with their defensive alignment and lineup construction.

Of course, the entire operation still revolves around Judge, whose absence cannot be overlooked when assessing this Yankees season. But as he approaches his 35th birthday in April, Judge’s injury-ravaged season is a reminder that his spectacular prime could already be behind him. At the very least, a stronger supporting cast is necessary for him to achieve his ultimate goal of bringing a World Series to the Bronx.

When Judge addressed the media a year ago as the Blue Jays partied in the Bronx, he had undoubtedly done his part in October, hitting .500 across seven postseason games, including a stadium-shaking, three-run homer in New York’s Game 3 victory against Toronto. In 2024, Judge was at the center of the collective letdown, having hit just .184 during New York’s postseason run and contributed one of the crucial errors in the fifth-inning defensive disaster in World Series Game 5.

This year, for the first time, Judge had to speak about a postseason in which he did not participate. This was also his least successful regular season as a big leaguer; his .871 OPS and 66 games played are both career-low marks in a full season. Injuries were the culprit; a rib fracture cost him three months, and a calf strain rendered him unavailable for the first two rounds of the postseason. It’s unclear if Judge would have been activated had the Yankees advanced, but the Rays rendered that what-if moot. Judge, the ultimate main character during this era of Yankees baseball, was relegated to looming large in the background.

That doesn’t make his words carry any less weight. 

“We’re the Yankees.”

Among a deluge of predictable post-elimination platitudes, these words uttered by the captain and three-time AL MVP in the wake of the Yankees’ latest postseason exit stood out. Judge had been asked what he hopes to see from ownership and the front office in response to the franchise once again failing to accomplish its annual goal of winning it all. 

“We’re the Yankees. I feel like they should go all-in and do what they need to do,” Judge said. “That’s why I signed back here to play with the Yankees: To fight for a championship every single year. To go all-in. That’s what I do every offseason, to get ready to give this team and this city everything we’ve got. I expect them to do the same.”

The intended sentiment is clear. It’s not just that the Yankees are dismayed after bowing out of the postseason early in October. It’s that this latest collection of Bronx Bombers has fallen well short of the singular standard of this franchise, based on its unrivaled history of being the last team standing.

Sure, the 2026 Yankees delivered their 34th consecutive winning season, the second-longest such streak in major-league history, behind a 39-year streak achieved by the Yankees from 1926 to 1964. The front office, helmed by Brian Cashman since 1998, has annually constructed ballclubs that reside at or near the top of the regular-season standings.

“But that’s not good enough here in New York,” Judge added. “We’re the Yankees. You have to go out there and expect championships and go all-in every year.”

They’re the Yankees. They’re different. They’re supposed to win it all.

In the first half of Cashman’s nearly three-decade tenure leading New York’s baseball operations, the Yankees won four World Series titles (1998, 1999, 2000, 2009), lost in the Fall Classic two other times (2001, 2003) and missed the postseason just once (2008). This is the standard that Judge and his fellow disappointed teammates grew up on. Those who become Yankees tend to embrace the franchise’s World Series-forward identity and aspire to uphold its tradition of winning.

But more recently, the Yankees have struggled to recapture the consistent excellence achieved by the previous generation. Over the past 14 seasons, New York has reached one World Series (2025) and missed October altogether on four occasions (2013, 2014, 2016, 2023). Since the Yankees last won the World Series in 2009, 10 different franchises have become champions, including their biggest rivals, the Boston Red Sox, twice.

So yes, they’re the Yankees. They still wear pinstripes and have a lot of terrific ballplayers. 

But whenever they do finally break through and win it all, there’s a good chance they will be exceeding expectations — not fulfilling them. 

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