What went wrong for the 2016 Yankees? And where do they go from here?

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

On Wednesday, it was the Tampa Bay Rays’ turn to take the honors from New York’s NCAA sweepstakes, following the Toronto Blue Jays’ dominating effort in the ALDS and the Los Angeles Dodgers in recent years by wrapping up five games in the 2025 World Series.

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In the ALDS sweep of Tampa, the Yankees pitching staff basically did its job, as it has all season. But without Aaron Judge, who was sidelined due to a calf injury in September, the Yankees’ offense has returned to the worst version of itself – a version that has been on display sans Judge for a long time. Only Ben Rice looked shutout in the distance, with the rest of the hitters showing little resistance to Tampa Bay’s host of weapons, which flummoxed New York’s bats no matter how manager Aaron Boone lined up. The Yankees struck out 31 times and recorded just 12 hits over three games, the last in the multigame streak in franchise history.

The end of Game 3 was a fitting finale for the “running-it-back” Yankees, a not-so-flattering moniker ascribed to them after New York spent the final offseason going to great lengths to keep its roster largely intact despite a first-season exit at the hands of Toronto. Last winter he worked on retaining Trent Grisham through a qualifying offer, re-signing key players Amed Rosario and Paul Goldschmidt, plus relievers Paul Blackburn and Ryan Yarbrough, and a huge new contract for outfielder Cody Bellinger – all while making minimal upgrades beyond returns.

Over time, some holdovers have done better than others. Blackburn excelled in relief, exemplifying New York’s developing competence and talent on the mound. Old Goldschmidt collapsed in the second half but failed to make a good move. Bellinger has shined all summer but wasn’t a factor against Tampa Bay, going 1-for-12. And after the sinking season, Grisham, who represented the Yankees’ last hope in the ninth inning of Game 3, was inserted into the leadoff spot as the last gasp of a pitch fired by Boone, with the hope that his discipline could show his much-needed plate. But while reaching second base, Grisham was hit by four pitches, leaving Rice on the docket and going 0-for-5 with three strikeouts.

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Fair or not, the prospect of the final at-bat of the 2026 Yankees season makes it hard to believe that running back will ever be a recipe for success. Now New York begins its journey again in early October with a chance to change its meaning. Early reports indicate that neither general manager Brian Cashman nor manager Aaron Boone is in danger of losing their job, so the number will be the focus.

Will they stir things up to a significant degree? Grisham is one of the Yankees’ key players to hit free agency, and it seems unlikely that he will stick around, especially given the emergence of outfielder Spencer Jones. Joining Grisham in the open market will be Jr. Jazz second baseman Chisholm and closer David Bednar, both of whom could command a significant sum in the free agent class. Bednar has been an excellent fit to back Boone’s bullpen this year, but the Yankees have proven capable of high-leverage innings without paying top dollar. They released Devin Williams and Luke Weaver in free agency last year; will they do the same with Bednar?

Chisholm’s fit with New York was more complicated. The Yankees infielder is both deeply upset and deeply upset. Is George Lombard Jr. lock day opening to be a shortstop? Could Antonio Volpe be in the basin or the third day every day, or be on the bench as a function? Does Ryan McMahon, still owed $16 million next season, have a place on this roster? And what about the middle season in addition to Luis Garcia Jr. — could he return to his country, despite his poor defensive reputation?

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And that’s just the infield. Giancarlo Stanton has a year remaining on his contract, but his durability is thin to say the least, and the DH spot will already be occupied by the likes of Garcia, Rice and possibly 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 a prominent (albeit expensive) rotation headlined by homegrown star Cam Schlittler. However, much remains to be done with the alignment of the defense and the construction of the lineup.

Of course, the whole operation still revolves around Judge, whose absence cannot be overlooked when evaluating the Yankees this season. But as he approaches his 35th birthday in April, Judge is reminded of his injury-ravaged season as his first show could be behind him. At the very least, he needs stronger support to achieve his ultimate goal of bringing the World Series to the Bronx.

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When Judge left the Blue Jays in the Bronx a year ago, he undoubtedly played his part in October, hitting .500 through seven postseason games, including a stadium-shattering, three-run home run in New York’s Game 3 victory against Toronto. In 2024, Judge was in the midst of a collective letdown, hitting just .184 against New York and contributing one of the crucial errors in a fifth-inning defensive disaster in Game 5 of the World Series.

For the first time this year, the Judge had to speak about the time he did not attend. Here, even in his smallest success, the times were as if they were faster than the great ones; His .871 OPS and 66 games played were both career highs in a full season. guilty of wrongdoing; a broken rib cost him three months, and a calf strain rendered him out of control for the first two seasons. It’s unclear if Judge would have been raised if the Yankees had advanced, but the Rays would have made a contentious return. Judge, the last major character in this era of Yankees baseball, has been relegated to a large circle.

What the words do not do is of less weight.

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“We are Yankees.”

Amidst the deluge of platitudes predicted after the elimination, these words from the manager and three-time AL MVP stood out in the wake of the Yankees’ latest postseason exit. Judge was asked what he expects to see from ownership and the front office’s response to the franchise once again failing to meet its annual deadline.

“We’re the Yankees. I feel like they’re all going to go in and do what they need to do,” Judge said. “That’s why we signed up here to play with the Yankees: to compete for the championship every year. To go all in. I do that every offseason, to be ready to give this team and this city everything we have. I expect them to do the same.”

The intention is clear. It’s not just that the Yankees were terrified behind the arc from the gridiron early in October. This latest collection of Bronx Bombers is well-missed by the unique organization of this franchise, based on its unique history of being the last team standing.

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

“But that is not enough for Paris,” adds the judge. “We’re the Yankees. You have to go out there and expect championships and everything to go away every year.”

They are Yankees. There are others. They are all supposed to win.

But are they really?

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In the first half of Cashman’s nearly three-decade tenure leading New York baseball operations, the Yankees lost four World Series titles (1999, 1999, 2000, 2009) in the Fall Classic two other seasons (2001, 2003) and missed the postseason just once (2008). This is a sign that Judge and his teammates have grown disappointed. Those who have become Yankees tend to embrace the World Series franchise’s forward identity and foster a winning tradition.

But more recently, the Yankees have tried to regain the excellence that was consistent throughout the previous generation. In 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.

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So are the Yankees. They still wear pinstripes and have a lot of terrific ballplayers.

But whenever they finally break through and win, there are a lot of good things to come, expectations not fulfilled.

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