The offseason is officially upon everyone. For the Yankees, though, their offseason began earlier than they would’ve liked. This team didn’t just miss out on a World Series rematch with the Dodgers. They couldn’t even make it past the Blue Jays, who outscored them by 15 runs in just four games and ended their ALCS hopes. “They dominated us in the regular season and the postseason,” Brian Cashman admitted. Despite their struggles in 2025, the Yankees are still seeing things a bit too optimistically while planning for the next season.

The Yankees do not feel the need to make any changes to their team, even though they failed to qualify for the ALCS this season. In the wake of a thrilling World Series that did not include his team, Brian Cashman says, “I don’t understand how a rebuild could even be considered.”

As Cashman sees it, “We have a farm system that is producing. We have quality major leaguers winning MVPs and potentially getting Cy Young Award votes. And we have the best record in the American League (tied with Toronto at 94-68), and we have Gerrit Cole coming back, along with other guys.”

Cashman sure made some bold moves at the trade deadline. He also earned plenty of praise for it. In fact, when Cashman shook up the league this season by adding the best of defense, athleticism, and bullpen depth to an already power-packed lineup, it was clear that the Yankees had no excuse not to win it all. They had every piece in place, only until Toronto broke them apart in the Division Series.

Still, as per the Yankees GM, his players only fell short in the postseason. Cashman seemed fairly satisfied with how the Yankees performed during the regular season. “We had a better record than the Dodgers did… but in the postseason we didn’t play to the best of our abilities.” He said. “Our intent is to always try to win the World Series.”

Good intent. But it would’ve been better if the Yankees got it before Aaron Judge was too old to enjoy it. He turns 34 in April and is likely to win his third AL MVP in four years. Still, you can bet he’d trade every personal award for a championship ring with his team. It’s the one thing that would end the constant talk about never winning the big one.

The Yankees have to fill these gaps ahead of the 2026 campaign

The Yankees have got to re-sign Cody Bellinger. Well, Bellinger has already proven how well he fits with the Yankees. His ability to play center field adds much-needed defensive flexibility. Now, in fact, his left-handed swing is perfect for Yankee Stadium’s short right-field porch. His 2025 home run spray chart says it all. Plus, he rarely strikes out, and that’s something this strikeout-prone lineup could really use.

With all that in mind, it wouldn’t be surprising if the Bronx Bombers made re-signing the 30-year-old Bellinger a top priority this offseason.

Moreover, the Yankees have done well trading for outfielders in recent offseasons. They landed Juan Soto and Trent Grisham from the Padres in 2023, then added Bellinger from the Cubs last year. This winter, they could look that way again. Randy Arozarena, Steven Kwan, Adolis García, Taylor Ward, Jo Adell, Brendan Donovan, and Luis Robert Jr. are among the top names who might be available.

The Yankees do need a right-hand batter to their squad. They should make use of this year’s market as there are plenty of affordable veteran outfielders who hit right-handed, including former Yankees star Harrison Bader. The other batters in the free agent column are Rob Refsnyder,  Miguel Andujar, Outfielder Tommy Pham, Kiké Hernández, Starling Marte, and Lane Thomas.

What are your thoughts? Do the Yankees need a change in strategy?