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The Yankees’ Playoff Dreams Are Over. Their Offseason of Questions Is Just Beginning.

After falling to the Red Sox in the wild-card game, New York faces a winter of massive change. Will Aaron Boone be the manager in 2022? What will happen to Gary Sánchez? And what will the team decide about Aaron Judge’s potential extension?

Getty Images/Ringer illustration

There’s no comfortable way for the Yankees to be eliminated from World Series contention. They’ve run the gamut in recent years: losing a Game 7, losing on a walkoff home run, losing to division foes by a single run. But even amid that litany of misery, Tuesday brought a whole new level of playoff pain: losing a winner-take-all contest in front of 38,000 delighted Red Sox fans at Fenway Park.

The much-anticipated new entry to the storied rivalry fizzled out early for New York: Gerrit Cole allowed a two-run home run to Xander Bogaerts in the bottom of the first inning, Nathan Eovaldi and four relievers quieted the Yankees offense, and the team’s one real chance for a comeback was thwarted by a strange send that got Aaron Judge thrown out at the plate. Boston won 6-2 to advance to the ALDS, leaving New York to confront another premature playoff failure.

The team’s magical run to Game 7 of the 2017 ALCS, which seemed like the start of the next great Yankees dynasty, keeps retreating further into the past. New York has now qualified for the playoffs five seasons in a row (only the Dodgers and Astros can say the same) and been competitive every time—but it hasn’t reached the World Series since 2009, and for this franchise, “competitive” isn’t enough. The climb back to the top of the sport won’t get any easier considering the state of the roster heading into 2022.

Contrary to preseason expectations, pitching wasn’t the problem for the Yankees in 2021. Their pitchers ranked fourth in fWAR, with both the starters (sixth) and relievers (third) enjoying strong production despite numerous injuries. And the group looks fairly set for next season, with Corey Kluber the only starter poised to depart from this year’s team. Cole, Jordan Montgomery, and Jameson Taillon will surely remain in the rotation. Luis Severino should stretch out as a starter with a full healthy offseason. Nestor Cortes Jr. deserves a long look after his breakout 2021 (2.90 ERA in 93 innings with healthy peripherals). And that quintet doesn’t include Domingo Germán, Michael King, or any of the prospects clamoring for a promotion from Triple-A.

Enticing arms are available in free agency this winter: Brian Cashman has long had eyes for Robbie Ray, for one, and Justin Verlander could reprise Kluber’s role as a former Cy Young winner recovering from a lengthy injury. But given the Yankees’ offensive needs, it would register as something of a surprise if they devote significant resources to the pitching staff.

Instead, those resources need to go toward addressing severe offensive problems. Despite retaining most of the lineup that led the American League in runs in both 2019 and 2020, this season’s Yankees ranked 10th out of 15 AL clubs in runs, with a 101 wRC+. That means they were only 1 percent better than average as a team. The franchise’s only seasons with worse offensive production since its 29-year streak of winning seasons began came in 2013, 2014, and 2016—all campaigns in which the Yankees missed the playoffs.

Even more troubling is that they did so relatively poorly with Judge and Giancarlo Stanton essentially maxing out their production, combining for 1,212 plate appearances and both ranking in the top 20 in park-adjusted offense. The problem was that the titanic twins didn’t receive much help from their teammates. Judge (5.9) and Stanton (3.1) were the Yankees’ only position players worth even 2 WAR, per Baseball-Reference. DJ LeMahieu (1.5) and Brett Gardner (1.0) were the only other players worth 1. On a team level, the Yankees suffered below-average production at every non-pitcher position except right field and DH.

That imbalance and overall offensive impotence manifested in the wild-card loss to Boston. The team recorded 11 strikeouts, six hits, and zero walks, and just one runner reached scoring position all night. Outside the top three hitters—Anthony Rizzo, Judge, and Stanton, who lined a home run and launched two towering singles off the Green Monster by himself—the Yankees’ hitters went a collective 1-for-20.

Heading into 2022, the Yankees have some reasons for optimism. They’ll get a full year of Joey Gallo, who struggled in half a season in New York after being acquired from the Rangers at the trade deadline, but has a long and more impressive track record at the plate. Aaron Hicks should return after a wrist injury limited him to 32 ineffective games in 2021. And LeMahieu could more closely resemble his 2019 and 2020 form after underperforming his Statcast-expected stats in 2021.

Yet other areas feature glaring question marks. Most notably, Gleyber Torres has regressed on both defense and offense. In the former, the Yankees moved him off shortstop in September due to repeated struggles at the demanding position; in the latter, Torres has managed just 12 total homers over the past two seasons and dipped below a .700 OPS in 2021. That’s a far cry from a 2019 effort in which he crushed 38 homers and received MVP votes.

Coincidence or not, Torres perked up after moving back to second base, with a .300/.372/.443 slash line at the position, and the Yankees surely hope that brief bounceback is a sign of a broader resurgence to come. They need one: Torres was the only 25-or-under Yankee with more than 25 plate appearances this season.

But his move back to second base opens a gaping hole at shortstop, where Gio Urshela does not seem like a long-term solution. Fortunately for a team that can outspend any other if it wants, its biggest hole has the most attractive options available: Carlos Correa, Corey Seager, Marcus Semien, Trevor Story, and Javier Báez are all poised to enter free agency.

Far fewer options are available behind the plate, if the Yankees decide to move on from Gary Sánchez with one more arbitration year remaining before the oft-criticized catcher reaches free agency. One winter after J.T. Realmuto was available and two winters after Yasmani Grandal signed with the White Sox, this class of free-agent catchers is headlined by Yan Gomes and Manny Piña. First base could also yield a change, with Rizzo set to become a free agent and Luke Voit having seemingly fallen out of favor with the club.

As they pursue upgrades to the 2022 lineup, the Yankees must balance those near-term concerns with another, longer-term expensive proposition: a potential extension for Judge, who’s set to reach free agency after 2022. Negotiations with the Yankees’ best hitter could prove complicated. On the one hand, Judge ranks third in park-adjusted offense (behind Mike Trout and Juan Soto) over the last half-decade, and fourth in fWAR (behind Trout, Mookie Betts, and José Ramírez). Among outfielders, he’s saved the third-most runs (behind Betts and Kevin Kiermaier).

On the other hand, Judge carries an extensive injury history: He’s qualified for the batting title only twice. And given the late start to his career, he will celebrate his 30th birthday before reaching free agency, increasing the risk of a long-term deal. New York’s apparent reluctance to push beyond the luxury tax threshold—to the extent that the current luxury tax structure will continue after the owners and players agree to a new CBA—might hamper its willingness to simultaneously sign a top free agent or two and extend Judge, even if that’s the best and most obvious path to boost the lineup back to championship-caliber.

The final big question for the Yankees is whether the team will replace Aaron Boone as manager. Boone has the second-best winning percentage among MLB managers since 1950 (.601), behind only the Dodgers’ Dave Roberts. But given the team’s uneven performance since 2019 and fans’ general abrasiveness toward Boone’s tenure, it wouldn’t be a huge surprise to see the organization search for a new skipper.

To this end, Boone’s situation serves as a microcosm for the broader team. The Yankees, and Boone, are good. But are they good enough to satisfy the demands of the organization?

The Yankees, after all, just posted the worst run differential (+42) for any AL playoff club, and a worse run differential than the Blue Jays (+183) and Athletics (+56) as well. They qualified for the playoffs by a single game because they outperformed their Pythagorean record by six wins, and in their division next season, fellow playoff clubs Tampa Bay and Boston will likely still be competitive while Toronto looks ready to ascend to the top of the AL East. Forget a World Series title; the Yankees have won just a single division crown since 2012, and have now played in the most wild-card rounds of any MLB club.

Just a few years ago, the Yankees appeared on the cusp of another dynastic run, full of youth and depth and star power and money. That run never emerged. For all its potential, the current core has never surmounted all the necessary hurdles to fulfill its promise, and now comes, perhaps, the most tumultuous offseason in recent franchise history. Like Stanton’s would-be game-tying home run in Tuesday’s sixth inning, for the last half-decade, the Yankees have come close, but not close enough.