Another year, another early playoff exit.
This one feels a little different, as not only could the Yankees not catch the small-payroll Rays in the AL East, they were swept out of the ALDS by their divisional foes. Their World Series title drought is now 17 years — the longest stretch since the Yankees won their first championship in 1923.
Now, they head into an especially uncertain offseason — for both themselves and the sport.
And in his closing comments after Wednesday’s loss, their most important player — Aaron Judge — had a message for the front office: “We’re the Yankees. I feel like they should go all-in and do what they need to do and if we’ve got holes, it’s finding certain players or personnel, whatever we need, we’ve got to go out there and get it.’’
Complicating matters is the fact that MLB is almost certainly going to face another lockout when the collective bargaining agreement expires on Dec. 1 and there are fears that it may last deep into next year, with the landscape of the game potentially changing significantly, as the owners seek to implement a salary cap.
With all that in mind, here’s a look at some of the key decisions the Yankees have to consider:
Leadership
The most important issues the Yankees face this offseason are at the top: Does Hal Steinbrenner want general manager Brian Cashman to continue to lead baseball operations? And if Cashman does return, does the longtime executive want to keep Aaron Boone as manager with one year remaining on Boone’s deal?
Cashman endorsed Boone before the Yankees’ season-ending loss to the Rays in Game 3 of the ALDS, saying, “I think Boone’s a really good manager. We’re here for a reason. There’s a lot of reasons behind that. And he’s certainly part of that.”
Boone, following the sweep, said he “of course” expected to return, adding, “Those conversations are for another day.”
As for Cashman, the last time his contract ended, it wasn’t renewed until later in the offseason.
Free agent position players
The Yankees’ offense went cold in the ALDS without Judge — as well as for long stretches during the slugger’s absence during the regular season.
Part of that was due to down seasons from Jazz Chisholm Jr. and Trent Grisham.
Grisham is almost certainly a goner, with his production with both his bat and glove deteriorating this season after getting the qualifying offer last offseason.
Chisholm is eligible for the qualifying offer, but it seems increasingly unlikely the Yankees give it to the second baseman, who followed up a breakout year with a rough one filled with mistakes.
Chisholm didn’t start against right-hander Nick Martinez in the clincher, another bad sign for the lefty-swinging infielder.
Veteran bats Paul Goldschmidt and Amed Rosario will also be free agents.
Goldschmidt was valuable as a righty-hitting option at first base and could return under the right circumstances, but Rosario played poorly all season.
Free agent pitchers
The strength of the Yankees, their starting rotation, should remain largely intact, but the bullpen is another matter.
Closer David Bednar is set to hit the open market and is coming off a strong season in The Bronx. He figures to be at or near the top of the list when it comes to who the Yankees look to retain.
Blackburn emerged as a key, late-inning right-handed arm after resigning with the Yankees last offseason, who value his ability to pitch in high-leverage situations.
Lefties Tim Hill and Ryan Yarbrough have provided valuable innings over the years in The Bronx, while Jon Schreiber and Michael Fulmer, two late-season signings, will also be back on the market.
Who’s on first?
As we look towards 2027, the only spot in which the Yankees are set in the infield is at shortstop, where George Lombard Jr. appears ready to stick for years to come- defensive miscues notwithstanding.
The Yankees could go with Luis García Jr. at first base, but they may also want to open that spot for Ben Rice if Giancarlo Stanton is able to stay healthy and can serve as the DH. Either way, they’ll look to make a change at second, since García can’t play there every day.
Could that be Anthony Volpe, who breathed new life into his career after losing his shortstop job to Lombard, or do they look to sign someone like oft-mentioned target Luis Arraez?
Moving around the diamond brings us to third base, where Ryan McMahon took a big step back with his defense — which was his calling card when he was acquired from the Rockies in 2025. He was also benched against a righty in the postseason, but is owed $16 million next season.
And back to Stanton, what can the Yankees expect from the injury-prone DH who missed almost the entire year with calf injuries?
Their outfield situation appears to be more set, with the always reliable Cody Bellinger in left and perhaps Spencer Jones as the answer in center.
But Heliot Ramos was a huge disappointment after coming over from San Francisco at the deadline and another year has passed and Jasson Domínguez still hasn’t proven he’s an everyday player, leaving his future with the organization in doubt.
Of course, Judge has to stay healthy for any of their roster moves to matter.
The Yankees overcame his absence to get to the postseason, but they were no match for Tampa Bay without him and clearly aren’t a World Series threat unless he’s in the lineup.
Catching up
The Yankees looked into upgrading the catching spot at the trade deadline, but ultimately stayed with Austin Wells, who was among the worst hitters in the game in the first half of the season.
He steadied himself at the plate after the All-Star break and was one of the few bats that did anything against the Rays, but they need some help in the area.
They pursued Ryan Jeffers from the Twins at the trade deadline, but he stayed in Minnesota. Perhaps they look to him again in free agency.
Go beyond the box score with the Bombers
Sign up for Inside the Yankees by Greg Joyce, exclusively on Sports+.
Thank you
Making a pitch
While the rotation is in good shape with Cy Young favorite Cam Schlitter, Gerrit Cole, Max Fried, Carlos Rodón and Will Warren all healthy — along with Ryan Weathers and perhaps Clarke Schmidt — there are plenty of questions about the pen.
They could look at Raisel Iglesias, the Atlanta closer that has long intrigued the Yankees, although he turns 37 in January.
Adrián Morejón, the left-hander the Yankees looked into at the deadline before he stayed in San Diego, is also a free agent.
And then there’s hard-throwing Carlos Lagrange, the fireballing righty the Yankees hoped might provide innings out of the pen, but was unable to recover from a shoulder injury in time to make his debut.
