5 questions facing the Yankees heading into the offseason

With a three-game sweep at the hands of the Rays in the American League Division Series completed late Wednesday night, the 2026 book officially closed on the Yankees, who have not won a World Series since 2009.

Manager Aaron Boone, who before the 2025 postseason said he felt as good about that group as any of his previous six teams that had made the playoffs, in terms of its potential to win a championship, said something similar entering the 2026 postseason.

Instead, like last year, the season ended in the American League Division Series and, like last year, against a team that beat out the Yankees for the AL East title.

In 2025, the Blue Jays defeated the Yankees in a four-game ALDS. This year, the Yankees were done in three games in the best-of-five series.

The sport’s looming labor issues are expected to result in an extended lockout when the current CBA expires at midnight on Dec. 1, but once the World Series ends, there will be roughly a month for teams to work on their rosters. With that in mind, here are five key questions for the Yankees entering an offseason of uncertainty:

1. Will they stay or will they go?

That, of course, is in reference to manager Aaron Boone, who just finished his ninth season as manager and who has one year left on his contract, and Brian Cashman, the club’s general manager since 1998, whose contract expires at the of October. There has been no indication that owner Hal Steinbrenner, consistently a staunch backer of both Cashman and Boone over the years, is looking to move on from either one, and that was the case even without the threat of the sport shutting down in less than two months. The anticipated prolonged labor war makes it even less likely that Steinbrenner will make that kind of significant organizational change before a shutdown that could last for months.

2. Who’s on second?

It is close to a lead-pipe cinch that, if there is a 2027 season, the answer won’t be Jazz Chisholm Jr. He arrived via trade at the 2024 deadline viewed in equal measures as a dynamic player with five-tool potential and a potential problem because of an immaturity that shows itself in some head-scratching moments, frequently at the worst possible times. Though popular overall with his teammates because of his generally amiable, outgoing personality, that popularity showed signs of fraying early in the 2025 postseason when Chisholm pouted after not starting against Boston in Game 1 of the Wild Card Series against tough lefty Garrett Crochet. His lollypop stunt, and the reaction to it, in Detroit this June didn’t go over nearly as well with his teammates as they publicly let on.

3. So who is on second? And third? And first?

Trade deadline acquisition Luis Garcia Jr. played a better-than-expected first base, but the Yankees may want to see if emerging star Ben Rice can become a reliable option there, too, especially if Giancarlo Stanton, whose only position is DH, is healthy (Stanton being healthy, of course, is always a big “if”).

Though Ryan McMahon is under control through next season, the Yankees might try to move on after a disappointing first full season in pinstripes both at the plate and in the field. Anthony Volpe, supplanted by George Lombard Jr. at shortstop, bolstered an already standout organizational and clubhouse reputation by digging in and adapting to second base in the minors. It wouldn’t be surprising if Volpe entered spring training with the starting job at second his to lose. The speedy and supremely valuable Jose Caballero can more than adequately play third, short and second, but he’s not viewed as an everyday option at any of the three.

4. Are the kids all right?

As bad as the ending to the season was, the Yankees saw four potential franchise cornerstones — and maybe a fifth — emerge. There’s the 27-year-old Rice, who hit 41 homers in becoming an All-Star for the first time, presumed American League Cy Young Award winner Cam Schlittler (25), outfielder Spencer Jones (25) and Lombard (21). Volpe, 25, who disappointed as the starting shortstop after his Gold Glove rookie year in 2023,  thrust himself back in the mix with his work in the minors after losing his job to Lombard and fighting his way back to the majors as an option at second base.

5. Have the Yankees wasted an in-his-prime Aaron Judge?

That's not a question that can be, or will be, answered concretely this winter, but it is an intriguing one. Judge, likely a shoo-in for Cooperstown even if he were to never again play in a big-league game (he is expected to be fully healthy by spring training), played in only 66 games this season, sidelined first with a right rib stress fracture and then with a right calf strain that cost him the entire postseason. Judge, a three-time American League MVP and eight-time All-Star, at the start of the 2027 season will be only two years removed from the third of those MVPs, as he nearly won the AL Triple Crown in 2025. But next April 26, Judge will turn 35.

By Erik Boland

erik.boland@newsday.comeboland11

Erik Boland started in Newsday's sports department in 2002. He covered high school and college sports, then shifted to the Jets beat. He has covered the Yankees since 2009.