Christmas is rapidly approaching, and it’s hard to fault any New York Yankees fans for expecting a sparsely-packed stocking. Now, we won’t go so far as to say they’ll find it full of coal — or even entirely empty — considering that the team has missed the playoffs only once since the start of 2017 and they have one of the sport’s top players in superstar outfielder Aaron Judge.
However, the Yankees have had opportunities to go shopping this winter, and they’ve mostly passed or opted for the bargain bin. Outfielder Cody Bellinger remains a free agent, and the Yankees still could use another starter in the back of their rotation. There’s also the pressing question of what the Yankees will do with former top prospect Jasson Domínguez, who turns 23 in February but seemingly has an increasingly uncertain role in the team’s long-term plans.
For the Yankees to achieve their offseason goals and improve their chances of winning their first World Series title since 2009, the club’s three most important figures — Judge, general manager Brian Cashman, and owner Hal Steinbrenner — must ensure that they’re all on the same page.
Aaron Judge needs to speak up and use his captaincy to his advantage
Theoretically speaking, the three most powerful in the Yankees’ organization should be the owner, the lead baseball executive, and the captain. Keep in mind that Judge is the 16th captain in team history and the seventh since the Steinbrener family took over in 1973. More often than not, the Yankees have a captain, and they don’t bestow the captaincy on a player by accident. Whether or not you believed that Judge had earned the right to be the Yankees’ captain when he did is irrelevant.
As things stand, Judge is the Yankees’ captain, and there are certain tasks that come with sitting atop the throne. When the Yankees’ season ended with an ALDS loss to the Toronto Blue Jays, Judge publicly said he wanted the Yankees to try to bring Bellinger and fellow outfielder Trent Grisham back for 2026. Grisham accepted the one-year qualifying offer, so he’s locked in and should begin next season manning center field.
Admittedly, we don’t know what Judge is saying behind closed doors. What we are arguing is that if Judge isn’t making his offseason preferences (read: demands) clear, then he needs to change his approach immediately. To be clear, the solution is not to suggest that Judge start screaming that Cashman and Steinbrenner shell out $1.5 billion in free agency. Nor do the Yankees stand to benefit from Judge essentially becoming the de facto president of baseball operations, with Steinbrenner solely seeking Judge’s input and icing Cashman out.
For the Yankees to hold off the likes of the Blue Jays, Dodgers, and Phillies en route to a 28th title, the triumvirates at the top are the key. Carlos Rodón and Gerrit Cole are likely to miss at least the 2026 season’s first month while recovering from elbow injuries, so Judge should be meeting with Cashman, Steinbrenner, and manager Aaron Boone to discuss veteran starting pitcher additions. Do the Yankees feel comfortable making Ben Rice the full-time starting first baseman? If not, then see how Judge feels, and if he has any ideas in mind on possible depth options.
By no means should Judge have the final say or dictate how the Yankees approach the offseason. There is a healthy balance of how much control and say that someone should have in a situation, and we’d like to think that Cashman and Steinbrenner are experienced enough to help determine that distinction. If the trio can’t get on the same page, and even more so if one of the three is willing to step up, then Yankees fans shouldn’t expect to enjoy a championship parade anytime soon — not unless they’re planning to take the train to Philadelphia, because the Phillies have certainly built a championship-caliber roster.