NEW YORK – The toughest part about being eliminated early in the postseason, according to Aaron Judge, is that no cheat code skips to October. Another 162-game gauntlet lies ahead, and if the Yankees want a different ending, their work must begin now.
“It’s not like, ‘Hey, we’re just going to run it back and we’ll be in the postseason,’” Judge said. “You’ve got to start back at 0-0 and work through the grind again. It’s just about trying to be 1% better every day in the offseason, and hopefully it will show up at the end.”
With that journey already underway, here are five questions facing the club this offseason:
Will there be changes at the top?
Aaron Boone was 11 minutes into his final postseason media address, around the same time the Rays were blasting Frank Sinatra’s “Theme from New York, New York” in the visiting clubhouse, when the manager was asked if he would like to return for 2027.
“Yeah, of course,” Boone said, adding, “Those things and conversations are for another day.”
The Yankees have more time than they’d like to evaluate their leadership situation. The more pressing issue concerns general manager Brian Cashman, who is nearing the expiration of his three-year contract.
Managing general partner Hal Steinbrenner has given no indication he plans to move on from Cashman, baseball’s longest-tenured GM, who has held the position since 1998. The last time Cashman’s contract was up for renewal, he continued working without a deal until the club announced an extension in December 2022.
Boone is under contract through next season, and Cashman has said he believes a manager's shelf life is about a decade. Joe Torre was in the job for 12 years, Joe Girardi for 10, and now Boone has completed nine.
Torre and Girardi delivered championships early in their tenures, however; Torre won his first of four in 1996, his first season, while Girardi triumphed in his second year in 2009. Boone has given the Yankees plenty of regular-season victories, posting a 790-565 (.583) record, but he’s 27-30 in the postseason and his clubs have been prone to fundamental lapses.
Changes could also come to the coaching staff, including pitching coach Matt Blake, whose contract is expiring.
What is the free agency picture?
The roster is set to shuffle, with second baseman Jazz Chisholm Jr., outfielder Trent Grisham and closer David Bednar among the prominent free agents. Chisholm and Grisham will likely play elsewhere next season, though Chisholm said after the ALDS that he wants to return.
“I do hope to be back,” Chisholm said. “I love it as a Yankee.”
Bednar could receive a qualifying offer worth $23.15 million, and the Yankees figure to explore re-signing reliever Paul Blackburn, who had a remarkable comeback season. First baseman Paul Goldschmidt said he intends to play in 2027, but he is expected to test the market.
Steinbrenner has often said it shouldn’t take a $300 million payroll to win a World Series, but the Yankees figure to be back in that neighborhood again.
They already have more than $205 million committed to seven players for 2027: Cody Bellinger (42.5M), Judge (40M), Gerrit Cole (36M), Giancarlo Stanton (25M), Carlos Rodón (27.8M), Ryan McMahon (16M) and Max Fried (31.5M).
Arbitration-eligible players like Luis García Jr. will add more. That increases the importance of young players like George Lombard Jr. and Spencer Jones continuing to develop, and on the front office to make deft moves in the trade market.
What does the future hold for Judge and Stanton?
Remember December 2017? The Yankees rattled the baseball world with a blockbuster trade for Giancarlo Stanton, pairing the reigning National League MVP with the AL’s Rookie of the Year in Judge. That slugging duo seemed poised to punish pitchers for years to come; Stanton said then that he would “feel sorry for the baseballs.”
Suffice it to say, 2026 wasn’t what either envisioned. Stanton barely played after late April, limited to two pinch-hitting at-bats in the postseason, while Judge missed 100 of 166 games due to a right rib fracture and a right calf strain. Judge wasn’t active for any of the playoff contests.
Judge is fanatical about his preparation, but as he approaches his age-35 season, the challenge is keeping his bat in the lineup. Their offense sagged without him, and though Judge won’t like hearing it, more frequent reps at designated hitter may be the best way to preserve his production.
Stanton’s role is unclear, with the DH spot already crowded. Ben Rice’s positional future is uncertain; the Yankees never got him behind the plate, and he lost first base reps after García's August acquisition. Expect the Yankees to bring Stanton into camp, but they can’t count on him. As Cashman has said, sustaining injuries “seems to be part of his game.”
Are the Yankees satisfied with Austin Wells?
Teasing a turnaround for his disappointing offensive season, Wells delivered three hits and four RBIs in the AL Wild Card Series sweep of the Red Sox. That optimism vanished with his ill-fated decision to try for third base late in ALDS Game 1 at Tropicana Field.
Wells has frequently said that handling pitchers and controlling the running game is his first priority, and he was named a Gold Glove finalist this week. But a .186 average and .624 OPS are difficult to ignore, especially considering Wells rose through the system as an offense-first prospect.
The Yankees tried to import a right-handed-hitting catcher at the Trade Deadline, with the Twins’ Ryan Jeffers and the Reds’ Tyler Stephenson among their targets. Both are set to become free agents and – at the least – could offer upgrades over backup Ali Sánchez, with the potential to challenge Wells for the starting role.
What’s next for Anthony Volpe?
Volpe made a telling remark when the Yankees recalled him from Triple-A Scranton/Wilkes-Barre in September, saying, “I never thought I was going to be back up here.”
Three years after being anointed as the starting shortstop, Volpe was demoted twice this past year and seemed like a prime change-of-scenery candidate.
But as Lombard took over in the Bronx, Volpe used his time in the Minors to his advantage, making subtle mechanical tweaks and becoming more comfortable at second base – a position where he looked fluid in a small sample size.
Now, with Chisholm unlikely to return, Volpe has a chance to stay at second base. He has an influential supporter in his corner -- Judge spoke highly of Volpe’s character and grit after the ALDS loss, saying, “If we were going to go win a World Series, we needed Anthony Volpe on the team.”