After a very similar team yielded the exact same result — an ALDS exit against a division rival — in 2025 and 2026, the Yankees enter this offseason with no shortage of roster questions.

Jazz Chisholm Jr. and Trent Grisham are set to be free agents, as are end-of-game relievers David Bednar and Paul Blackburn.

There are decisions to make on players under contract, too, as the Yankees seek to upgrade a heavily left-handed lineup that struggled without Aaron Judge and a defense that faltered in the playoffs.

“I want to trade for everybody and sign everybody every single year, but I know that’s not realistic,” Judge said Wednesday after the Tampa Bay Rays completed an ALDS sweep.

“So they give us a winning team every single year, but that’s not good enough here in New York. We’re the Yankees. You gotta go out there and expect championships and go all in every year, so I’m excited to see what they do.”

Complicating matters is a weak free-agent class, as well as the Dec. 1 expiration of baseball’s collective bargaining agreement, with a work stoppage all but certain to follow.

While teams will have a window to sign free agents before Dec. 1, the uncertainty over what the next CBA will look like — will there be a salary cap? — makes signing any big-money contracts before then a massive risk.

With all of that in mind, here are the Yankees’ biggest roster questions going into the offseason.

WILL JAZZ CHISHOLM JR. RETURN?

Chisholm, who turns 29 in February, expressed his desire to return, but the second baseman is coming off of a down season in which he batted .231 with 19 home runs, a .711 OPS and 41 stolen bases.

That’s after the lefty-swinging Chisholm hit .242 with 31 homers, an .813 OPS and 31 steals in 2025.

The Yankees have internal options to replace Chisholm, starting with Anthony Volpe, who — after being displaced at shortstop by George Lombard Jr. — graded well defensively at second base over a small sample.

Volpe, a former top prospect who is still just 25, is not the same level of hitter as Chisholm, as he batted .245 with two homers and a .658 OPS in 220 MLB at-bats this year.

But Volpe is likely due only a modest raise on last year’s $3.5 million salary as he enters his second year of arbitration. He performed well down the stretch, tearing the cover off the ball at Triple-A before batting .265 in the majors in September and going 3-for-7 in the playoffs.

It was notable that the Yankees, seeking a spark for a struggling lineup, started the righty-swinging Volpe at second base over Chisholm in a must-win ALDS Game 3.

Slugging first baseman Luis García Jr. also can’t be eliminated from the second-base equation, as made 508 appearances at the position with the Washington Nationals. But García graded poorly defensively as a second baseman and did not see any time there after his midseason trade to the Yankees.

Externally, the top free agents include Brandon Lowe (35 homers, 96 RBI in 2026) and contact-hitting Luis Arraez (.310, six homers), who both bat left-handed.

HOW ABOUT TRENT GRISHAM?

After hitting 34 home runs with an .811 OPS in 2025, Grisham played on the one-year, $22 million qualifying offer this season and failed to match that production.

Grisham hit .211 with 18 homers and a .703 OPS in 2026 while navigating a pair of IL stints for hamstring strains.

Perhaps more starkly, the center fielder regressed again defensively, ranking in MLB’s 10th percentile with -5 Outs Above Average (OOA) and in the 19th percentile with a -5 Fielding Run Value, per Statcast.

It was the second year in a row that Grisham, a two-time Gold Glove Award winner, graded below average on defense.

Grisham, who turns 30 next month, has loved his time as a Yankee, and the team admires the veteran’s patience and control of the strike zone.

But 25-year-old Spencer Jones impressed as a rookie, hitting 11 home runs and a .742 OPS in 261 at-bats, making a case for the starting job.

His defense in center field remains a work in progress, but Jones possesses the speed and tools to improve — and playing between Judge and Cody Bellinger should help his development.

DOES THIRD BASE NEED REINFORCEMENTS?

Ryan McMahon’s glove has always been his bread-and-butter, but after a subpar defensive season, third base is a big question for the Yankees.

McMahon posted 0 OAA and a 0 Defensive Fielding Value, while another advanced metric, Defensive Runs Saved, had him at -3.

That’s on top of the lefty-swinging McMahon hitting .213 with 11 homers and a .635 OPS.

All of that made McMahon worth 0.0 wins above replacement (WAR), according to Baseball Reference, meaning he was a true replacement-level player in 2026.

McMahon is due $16 million in 2027 for the final year of his contract, but that shouldn’t preclude the Yankees from seeking an upgrade at third.

José Caballero saw considerable time at third base down the stretch, particularly against left-handed pitching, but the Yankees prefer him in a utility role.

The problem is that third base is a weak free-agent position, with 30-year-old Alec Bohm (15 homers, 88 RBI, .698 OPS) among the better options there.

Volpe worked at third base a bit at Triple-A this year and could enter that mix, too, if the Yankees go in another direction at second.

HOW WILL YANKEES ADDRESS THEIR BULLPEN?

The Yankees boasted MLB’s second-best bullpen in 2026, with the unit pitching to a 3.15 ERA.

Two of the biggest reasons for that success might not be back, as the closer Bednar and the multi-inning weapon Blackburn are both due for free agency.

The Yankees haven’t been big spenders on their bullpen in recent years, with offseasons like 2019 — when they signed Zach Britton ($39 million) and Adam Ottavino ($27 million) to three-year deals — feeling like a very distant past.

Instead, they’ve relied on developing or untapping bullpen arms, with Blackburn, Brent Headrick and Luke Weaver among the successes.

Still, it wouldn’t be surprising to see Bednar (2.47 ERA, 35 saves in 39 chances) or Blackburn (1.69 ERA in 85 innings) come back, though both would require raises.

Bednar, a candidate for the qualifying offer, made $9 million last season. Blackburn made $2 million.

There isn’t an obvious internal option to replace either, and particularly Bednar.

Headrick (2.18 ERA in 78.1 innings) is the Yankees’ top reliever under team control, while Tim Hill, John Schreiber and Ryan Yarbrough are also set to be free agents.

Fernando Cruz (3.13 ERA in 54.2 innings) is arbitration eligible and hopes to continue pitching through a partial tear in the UCL in his right elbow.

They Yankees do have a surplus of starting pitching, but rotation depth is too important for them to consider moving anyone to the bullpen yet.

GIANCARLO STANTON’S FUTURE?

Three separate calf strains caused Stanton to miss the final five months of the regular season, and he was limited to pinch-hitting duties when he returned for the playoffs.

Given his injury history, the Yankees can’t plan on Stanton being part of their everyday lineup in 2027, though they effectively already filled that void by acquiring García before the trade deadline.

Stanton is due $25 million in 2027, with the Miami Marlins kicking in $10 million of it. The Yankees then hold a $25 million club option for 2028 with a $10 million buyout.

Even with García at first and Ben Rice at designated hitter, Stanton’s powerful right-handed bat could provide value in a part-time role, so long as he’s healthy.

But carrying all three on the Opening Day roster would likely prevent the Yankees from adding another first base/DH type, such as Paul Goldschmidt, a free agent who remains a weapon against left-handed pitching.

It also wouldn’t hurt for the Yankees to find more DH at-bats for Judge, who is coming off of an injury-plagued season and turns 35 in April.

The Yankees haven’t shown much interest in moving Rice back to catcher — a demanding position that could compromise his important, 41-homer bat.