Three questions facing the New York Yankees this offseason

For most teams, the New York Yankees had a successful season. However, as the season did not end in a World Series championship, 2025 was a disappointment.

That the Yankees even got as far as the ALDS is a bit of a surprise. Staff ace Gerrit Cole was lost for the season in spring training as he required Tommy John surgery. Luis Gil made just 11 starts due to a strained right lat. The Yankees' attempt to fortify the bullpen at the trade deadline failed as relievers Jake Bird and Camilo Doval struggled. 

The Yankees have a lot of work to do if they are going to win their first championship since 2009. A battered rotation will be missing three starters at the beginning of the 2026 season. Outfielder Cody Bellinger will opt out of his contract, leaving a gaping hole in the lineup. The Yankees have more questions than answers as the offseason approaches.

Three questions facing the New York Yankees heading into the offseason

1. Can the Yankees bring Bellinger back?

2025 marked the second consecutive year that the Yankees acquired someone to protect outfielder Aaron Judge in the lineup. Juan Soto ended up being one and done for the Yankees, turning them down in free agency to sign with the crosstown Mets. History could repeat itself as Bellinger will reportedly opt out of his contract to test free agency once more.

Although he was unable to replicate Soto's performance, Bellinger still had a strong season in New York, posting a .272/.334/.480 batting line with 29 homers and 25 doubles over 656 plate appearances. His ability to play all three outfield positions and first base provided flexibility for a Yankees roster that sorely needed it. Likewise, Bellinger is seemingly made for Yankee Stadium, posting a .302/.365/.544 batting line with 19 homers in 337 home plate appearances. The Yankees cannot afford to lose Bellinger as they continue to look for an answer behind Judge in the lineup.

2. What to do with outfielder Jasson Dominguez?

Dominguez had begun the season as one of the favorites for the AL Rookie of the Year award. Instead, he disappointed in his first full major league season, posting a .257/.331/.388 batting line with 10 homers and 18 doubles over 429 plate appearances. He lost playing time down the stretch, making just 29 starts as he struggled in the second half.

At 22 years old, Dominguez still has plenty of time to develop into the player he was projected to be. However, for that to happen, he needs playing time. The Yankees, while aiming for a championship, need to be patient through his growing pains. Otherwise, Dominguez may be better off as a trade chip for the Yankees to bring in another veteran bat.

3. How much longer should general manager Brian Cashman get?

Cashman is the longest tenured GM in the majors, having been promoted to the role on February 3, 1998. He has been in his position for more than 16 years longer than the second-longest tenured GM (A.J. Preller of the Padres). It is difficult to argue against his success, as the Yankees have missed the postseason just five times, have never had a losing record, and have won four World Series titles. However, that success comes with a caveat, as three of those titles came from 1998 through 2000 — one championship in the past 25 years is not good enough for the Yankees.

Aside from a brief conflict with George Steinbrenner and a territorial squabble that prompted Cashman to consider leaving the franchise after the 2005 season, he has been unfailingly loyal to the Yankees. The Yankees have repaid that loyalty over the years. However, the game eventually passes everyone by. As the Yankees have only had two stretches where they went longer without a championship, it is fair to wonder if the game has begun to leave Cashman behind. The best option may be to promote Cashman higher up the chain, but have someone else take over constructing the roster.