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.
uncertain
they → feel → foes
Their World Series title drought is now 17 years — the longest stretch since the Yankees won their first championship in 1923.
asserted
Yankees → win → 1923
Now, they head into an especially uncertain offseason — for both themselves and the sport.
asserted
they → head → themselves
Try it freeAnd 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.
asserted
We → try → office
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:
uncertain
Yankees → feel → decisions
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?
asserted
Cashman → face → 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?
asserted
executive → return → 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.
asserted
Boone → endorse → ALDS
We’re here for a reason.
asserted
We → ’re → reason
And he’s certainly part of that.”
asserted
he → ’ → that
Boone, following the sweep, said he “of course” expected to return, adding, “Those conversations are for another day.”
asserted
conversations → follow → day
As for Cashman, the last time his contract ended, it wasn’t renewed until later in the offseason.
asserted
it → end → offseason
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.
asserted
offense → go → season
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.
asserted
production → deteriorate → offer
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.
asserted
who → qualify → mistakes
Chisholm didn’t start against right-hander Nick Martinez in the clincher, another bad sign for the lefty-swinging infielder.
asserted
Chisholm → start → infielder
Goldschmidt was valuable as a righty-hitting option at first base and could return under the right circumstances, but Rosario played poorly all season.
uncertain
Rosario → hit → circumstances
The strength of the Yankees, their starting rotation, should remain largely intact, but the bullpen is another matter.
asserted
bullpen → remain → Yankees
Closer David Bednar is set to hit the open market and is coming off a strong season in The Bronx.
asserted
Bednar → set → Bronx
He figures to be at or near the top of the list when it comes to who the Yankees look to retain.
asserted
Yankees → figure → who
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.
asserted
who → emerge → 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.
asserted
Schreiber → provide → market
Who’s on first?
asserted
Who → ’ → 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.
asserted
Jr. → look → years
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.
uncertain
Stanton → go → DH
Either way, they’ll look to make a change at second, since García can’t play there every day.
asserted
García → look → second
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?
uncertain
they → breathe → 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.
asserted
he → move → 2025
He was also benched against a righty in the postseason, but is owed $16 million next season.
asserted
He → bench → million
And back to Stanton, what can the Yankees expect from the injury-prone DH who missed almost the entire year with calf injuries?
asserted
who → expect → 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.
asserted
situation → appear → 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.
asserted
he → come → doubt
Of course, Judge has to stay healthy for any of their roster moves to matter.
asserted
any → have → moves
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.
asserted
he → overcome → 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.
asserted
who → catch → 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.
asserted
they → steady → area
They pursued Ryan Jeffers from the Twins at the trade deadline, but he stayed in Minnesota.
asserted
he → pursue → Minnesota
Perhaps they look to him again in free agency.
asserted
they → look → agency
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.
asserted
Schlitter → make → pen
They could look at Raisel Iglesias, the Atlanta closer that has long intrigued the Yankees, although he turns 37 in January.
uncertain
he → look → January
…and 2 more, not listed.
The Aporia
