5 biggest questions Yankees are facing during 2026-27 MLB offseason
· Yahoo Sports
Another October thud, naturally, leads to winter questions, some quite thorny. Where do the Yankees go from here, apart from taking some time to process the ache of getting swept by the Rays in the AL Division Series?
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That’s consecutive ALDS exits against AL East rivals that were better than the Yanks during the regular season now, so the team must get better. How does that happen? There are important free agents looming, like closer David Bednar, so big decisions must be made. All those will come as the sport sorts through negotiations for a new labor agreement, which will have an as-yet unknown impact on the game’s economics.
Here are five Yankee storylines to follow during the offseason:
Will Aaron Boone be back?
The outside debate over whether the Yanks need a new dugout voice rages with every end of season loss (and often long before). Perhaps a culture jolt would be just the thing. But fans’ ire does not fire or hire when it comes to the Yankee manager, so Boone seems likely to stick.
He’s got one year left on his deal. A likely lockout would give a new manager little time to get set and get to know players. Big-name stars such as Aaron Judge and Cam Schlittler backed Boone after the Game 3 loss.
There’s also an easy way for the Yankees to talk themselves into letting Boone proceed -- Judge, probably the best hitter in the world, played only 66 games, none in the postseason. Other stars missed significant time, too. In a season of tribulation, the Yankees weren’t good enough, but they still won 93 games and beat Boston in the AL Wild Card Series. Boone has missed the playoffs once in nine years guiding the Yanks.
What does Judge’s “all-in” look like?
Judge urged the Yanks to go “all-in” and “go out there and get it” to fill whatever holes the team has going forward. How does that happen, especially in a generally-thin free agent market? The Yankees have some well-regarded young big leaguers who helped them get to the playoffs.
Do they get creative on the trade market with them and their prospects? Or do they trade peanuts for some team’s bad contract and hope they snag a player who is re-energized in the Bronx? They’d better do something, especially with a lineup that flagged during the season and then produced, well, that October.
It’s one thing to say that good pitching beats good hitting in the October cauldron, but the Yankees were dreadful on offense against the Rays, batting .130 with a .431 OPS. Even with the team missing Judge, they can’t be that awful. Without Ben Rice, would they have even scored at all? (We’re exaggerating, he only drove in three of the Yanks five runs in the series, but still).
There’s no wiggle room at designated hitter. Rice and Judge, who turns 35 in April, require at-bats there. Giancarlo Stanton has no position other than DH. Maybe they could steal from the Rays playbook and add players with big-time ball-in-play skills to diversify?
Second thoughts
Jazz Chisholm Jr. is a free agent and Anthony Volpe revitalized his career after being sent to Triple-A and returning with vigor. Perhaps Chisholm out, Volpe in is the easiest way to solve second base.
Jul 22, 2026; Bronx, New York, USA; New York Yankees shortstop Anthony Volpe (11) and second baseman Jazz Chisholm Jr. (13) react after winning against the Pittsburgh Pirates at Yankee Stadium. / John Jones-Imagn Images
It’s pretty unlikely Chisholm returns -- he did not live up to his big talent in his walk year, heard boos at Yankee Stadium and was so un-vital to the Yankee cause that Boone didn't start him in Game 3 against a righty.
The Yanks could make him a qualifying offer and get a draft pick when he signs elsewhere. But they’d have to be OK with him returning. He could just grab the $23-plus million and try to re-set his free agency with a bigger season on what figures to be a good Yankee team in ‘27.
Finally, the Yanks’ biggest deadline deal brought them Luis García Jr., a thunderous lefty bat. He played only first base for the Yankees and Nationals last year, but spent the previous three seasons as Washington’s second baseman. He’s played second, but can he PLAY second? Especially for a club that just embarrassed itself defensively this postseason.
Pen notes
The Yanks have done a remarkable job discovering and developing useful relievers for years, but that doesn’t mean they should overthink closer this winter. Bednar is a free agent. The Yankees should re-sign him. He recorded 35 saves and a 2.47 ERA in 64 games during the regular season and added three scoreless postseason innings.
He’s proven he can handle the New York market and his entrance song -- “Renegade” by Styx -- sounds cool.
Beyond Bednar, Paul Blackburn is another key bullpen free agent and he’s coming off an insane platform year -- a 1.69 ERA in 62 games and one hit allowed over six shutout innings in the playoffs. He’s a keeper, too.
Get defensive
We’ll stop short of using the term “run prevention” for obvious reasons, but the Yanks have had two high-profile defensive meltdowns in the postseason in the last three seasons and need to fix their defense. A few Dodgers chirped them after the Game 5 debacle in the 2024 World Series, but that wasn’t humiliating enough to prevent the Yankees from bungling Game 2 against the Rays with another torrent of miscues.
Another early October exit is, sadly for them, becoming familiar territory for these Yankees. But a near-annual blooper-fest in the playoffs can’t be on repeat, too. If it takes new defensive protocols, more infield practice during the season, more accountability or better defenders, it must stop.