Aaron Judge just picked up the 2025 AL MVP, adding another trophy to what’s already one of the most dominant runs we’ve seen in modern baseball. But even with all that, there’s still a noticeable gap in the story. The Yankees haven’t won a World Series since 2009, and it’s starting to feel like time is slipping away.

7x All-Star, 3x AL MVP, and 5x Silver Slugger Award, and more constitute Judge’s resume, but that one short of a World Series is what makes him go desperate. And you could hear that urgency in his comments after winning the MVP—there was a clear edge, a hint that he knows what’s missing. In a way, it felt like a message pointed straight at Brian Cashman… It’s time to get aggressive this offseason and build a team that can actually finish the job.

“I think I’d trade every award I’ve gotten and every All-Star appearance for an opportunity to win a championship,” MLB insider Bryan Hoch cited Aaron Judge.

The urgency behind the Judge’s message becomes even clearer when you look at the Yankees’ current window. Gerrit Cole, who has an opt-out after 2026, is entering his mid-30s, and the rotation behind him remains unstable with Carlos Rodón’s inconsistency, Nestor Cortes’ shoulder issues, and Clarke Schmidt still proving his durability.

Add in a bullpen that collapsed in the second half of 2025. The reality that New York plays in an AL East loaded with a rising Orioles core, an aggressive Red Sox front office, and a Blue Jays team fresh off a World Series run — and Judge’s call for action feels less like frustration and more like a necessary warning.

All these awards, and Judge would still gladly trade every one of them if it meant giving the Yankees a stronger, more complete lineup heading into 2026. And honestly, who can blame him? He just put up 53 HRs and 114 RBIs, only to watch the bullpen implode game after game. For a player performing at that level, it has to be frustrating to see the same weaknesses sink the team.

Hence, this offseason should be a turning point for the Yankees if they want to get back to the World Series race. But right now? It’s radio silence from the front office. Meanwhile, teams like the Blue Jays are already locking down their key players from last season, while New York hasn’t made a single aggressive move. No wonder Judge sounds like a guy who’d trade every personal milestone for a championship ring.

For the unversed, the Yankees wrapped up 2025 with a $319 million CBT payroll, and they’re projected to sit around $258 million for 2026 with arbitration factored in. So, even if they don’t raise payroll, they still have plenty of financial room to add the arms and bats they desperately need. The ingredients for a win-now offseason are all there. The real question is whether Brian Cashman will actually act on it.

Arming up the bullpen is a need of the hour for the Yankees

The Yankees could have gone beyond the ALDS had their bullpen not blown up a few close games. Last season’s bullpen was one of the weakest New York has had in years, and losing Williams and Luke Weaver to free agency strips away two of Aaron Boone’s most dependable arms.

So, what’s next?

A smart target would be Pete Fairbanks. He’s coming off a career year with 61 appearances and 27 saves, and he’d slot in perfectly as a setup man behind Bednar. The catch is that the Rays have a $12.5 million option on him for 2026. So, that might be steep for a team that rarely spends big. Although his only genuine concern is his injury history, he stayed healthy throughout 2025 and finished with a 2.83 ERA.

Robert Suarez is another option if the Yankees want to keep adding reliable late-inning arms. But none of this matters unless New York actually steps up and makes the moves. Otherwise, it could be a repeat of the painful misses on Yoshinobu Yamamoto and Roki Sasaki, opportunities that slipped right through their fingers.