The Yankees are set to keep Aaron Boone in the dugout for a tenth season, and the manager isn’t treating the contract situation like a distraction. Boone is under the two-year extension he signed in February 2025, which makes him the seventh skipper in franchise history to get to a decade with the club.
Hal Steinbrenner said Wednesday that no extension talks have taken place yet with Boone, though that doesn’t rule out future discussions. Boone, for his part, said managing on an expiring deal “doesn’t bother (him) at all.” He also noted that players and coaches often work without long-term security, even if many teams prefer to avoid having a manager or top baseball executive in a lame duck situation.
Brian Cashman is in a different spot, but one that appears headed toward more continuity too. The Yankees let their general manager operate on an expiring deal in 2026, and Cashman said Wednesday that he and the club were finalizing an extension.
If that goes through, it should push him close to three full decades in the job. Cashman became general manager in February 1998 and is already the longest-tenured active GM by a wide margin.
Matt Blake also seems likely to return, which fits given how strong the Yankees have been on the pitching side in recent years. The offense, though, is another story.
Steinbrenner was noticeably less settled when asked about hitting coach James Rowson, saying the club still had to discuss all of its coaching decisions. “I’m definitely focused on the offense and on the hitting,” Steinbrenner told reporters.
“I think it was a big part of, certainly a significant, part of why we didn’t achieve what we wanted to achieve.”
That concern is backed up by how badly the lineup sagged after Aaron Judge went on the injured list at the start of June. From that point on, the Yankees ranked 24th in scoring. Over the final four months of the season, only the Reds hit for a lower average, and New York’s .297 on-base percentage in that span was the worst in the majors.
Judge’s season was derailed by a rib fracture, and he returned in early September looking rusty over a two-week stretch before a right calf strain ended his year. Cashman said Judge would undergo follow-up testing on the rib, but the expectation is that he’ll be ready for Spring Training.
Even with the coaching picture still unsettled, the roster is bound to change. Trent Grisham and Jazz Chisholm Jr. are both headed for free agency and appear unlikely to be back. The Yankees also have decisions to make on Giancarlo Stanton and whether they need upgrades at third base and catcher over Ryan McMahon and Austin Wells.
Second base is especially worth watching. If the Yankees hand shortstop to George Lombard Jr., then Anthony Volpe and José Caballero become the leading internal options at the keystone.
On the market, Brandon Lowe, Luis Arraez, Chisholm and Gleyber Torres are all available. The trade route is there too, with Ketel Marte and Xavier Edwards mentioned as possibilities.
Edwards has reportedly drawn Yankee interest before, and Joel Sherman of The New York Post reported that Kansas City second baseman Michael Massey has also been on their radar. Massey, 28, hit .274/.305/.430 with 13 homers for the Royals this year.
His career has had its swings, and he struggled in 2025 around an ankle sprain, but he brings average power, puts the ball in play and profiles as a left-handed hitter with a pull-heavy fly-ball approach that could play at Yankee Stadium. His walk rate is low, which doesn’t exactly solve New York’s on-base issue, but he is viewed as a strong defender with a useful blend of hit and power.
The Royals are coming off a rough season, though a rebuild still doesn’t seem likely. Massey is under control for two more seasons and is projected by MLBTR contributor Matt Swartz to earn $3.2MM in arbitration. He’s the kind of player a team can move without treating him as untouchable, but Kansas City would presumably want major league pitching or outfield help in return.
In Other News...
Aaron Judge And Yankees Brass Are Suddenly Clashing Over One Big Issue
The Yankees are spending the early days of the offseason sorting through more than just the pain of another October exit. After their ALDS elimination, Aaron Judge publicly took aim at the roster and the way the club has been preparing, while Hal Steinbrenner has been digging into the offenses inconsistency and the organizations hitting-development structure. The result is an uneasy backdrop for a team that was supposed to be built around championship expectations, not internal questions about how it goes about chasing them.
Steinbrenners concern has extended to how players engage with the clubs analytics and development approach, which only sharpens the contrast with Judges view of the Yankees commitment and readiness. Those differing perspectives are now part of the larger offseason conversation, with the organization facing decisions that go beyond a few roster tweaks and into the deeper question of whether its methods still match its ambitions. [Read more 🡒]
Yankees Shortstop Search Could Cost Them A Prospect Fans Love
The Yankees search for stability at shortstop is already reaching into the kind of trade market that can reshape a roster, and Jeremy Pena is one of the names drawing real attention. The Astros shortstop has been productive, and at 29 he still fits a window that gives a contender some runway, but there are also defensive metric concerns that make any deal a little more complicated than a simple upgrade on paper.
For New York, the bigger issue may be the cost. Any serious pursuit would likely force the Yankees to part with young talent, and George Lombard Jr. is the type of prospect who could end up in the conversation. Houston has its own roster and contract decisions to sort through, which only adds another layer to a potential deal that would test how far the Yankees are willing to go to solve the position. [Read more 🡒]
Yankees Offseason Comes Down To Fixing One Problem Without Creating Another
The Yankees winter is shaping up around a familiar kind of problem for a contender: how to add offense without thinning out the pitching depth that still gives them a real path back into October. Center field, second base and third base all loom as areas that need attention, and with Trent Grisham and Jazz Chisholm Jr. likely headed for free agency, the front office has some meaningful holes to sort through before the roster starts to take shape.
The pressure is sharper at the infield corners, where the Yankees production at second and third base last season was among the worst in the league. That is why names such as Luis Arraez, Bo Bichette, Isaac Paredes and Jeremy Pena are already floating around the discussion, even if any move will have to be weighed against the clubs bigger goal of staying strong enough on the mound to get past the American League Division Series. [Read more 🡒]