Aaron Judge Admits Surprising Brian Cashman Frustration

With the Yankees staying mostly quiet this offseason, Aaron Judge isnt hiding his concern about how far that silence can take them.

The Yankees are rolling into 2026 with a familiar look - maybe a little too familiar for some, including their franchise cornerstone.

After a relatively quiet offseason, New York opted to bring back key pieces rather than shake things up. Cody Bellinger is returning on a five-year, $162.5 million deal.

Trent Grisham is back on a one-year, $22 million contract. And Paul Goldschmidt joins the mix on a one-year, $4 million deal.

That trio brings experience and upside, but the lack of fresh faces - especially high-impact ones - hasn’t gone unnoticed.

Aaron Judge, the reigning back-to-back AL MVP and the heartbeat of this Yankees team, didn’t hold back when asked how he felt about the team’s offseason approach.

"It was brutal," Judge said. "I see a lot of free agents out there... Let's sign these guys right now and then start adding more pieces."

You can feel the urgency in his words. Judge isn’t just looking at the Yankees through the lens of a player - he’s speaking like a leader who knows the clock is ticking.

At 33, with four seasons down on his nine-year, $360 million contract, Judge is fully aware that his prime won’t last forever. He’s chasing more than MVPs - he’s chasing a championship.

And after falling short in 2024 to Shohei Ohtani and the Dodgers, the hunger is only growing.

To Judge’s point, other contenders were aggressive this winter. Big trades, marquee signings - the kind of moves that signal a team is all-in.

The Yankees, meanwhile, seemed to take a more conservative route. That’s not to say they stood completely still.

Re-signing Bellinger was a must, and Grisham gives them a reliable glove and speed at the top of the lineup. Adding Goldschmidt, even at age 38, brings another veteran bat with postseason experience.

But for a team that hasn’t won it all since 2009, the bar is higher - and so are the expectations.

Judge did acknowledge the positives.

"I think once we solidified getting Bellinger back, we got Trent being our center fielder, being our leadoff guy for another year. You add a guy like Goldy... I think we'll be in a good spot."

Still, the early part of the offseason left him - and likely some fans - wondering if the Yankees were doing enough to capitalize on their current window. With a strong core in place and young talent emerging, this felt like the time to go big. Instead, they played it safe.

One move that flew under the radar but could pay off: the acquisition of left-hander Ryan Weathers from the Marlins. He’s got the stuff to eventually slot in near the top of the rotation if he can put it all together. That’s a gamble worth taking, especially given the volatility of pitching depth over a 162-game season.

But the reality is this: if the Yankees are going to make a serious run, they’ll likely need to be aggressive at the trade deadline. And that’s where things could get tricky.

With limited impact additions in free agency, the front office may have to part with top prospects to upgrade - including outfielder George Lombard Jr., currently ranked No. 32 in MLB’s top 100. That’s a steep price, but one that might be necessary if the Yankees want to keep pace with teams like the Dodgers, Braves, and Astros.

There’s also the question of durability. This roster is leaning heavily on veterans.

Bellinger, Judge, Goldschmidt - all proven, but all with miles on their legs. Without more depth or an infusion of youth, the margin for error is slim.

Injuries are inevitable. The question is whether the Yankees have enough behind their stars to weather the storm.

At the end of the day, the Yankees are betting on continuity, chemistry, and the leadership of players like Judge to carry them through. It’s a calculated risk - one that could pay off if the core stays healthy and the front office is willing to pounce at the right time.

But make no mistake: the pressure is on. And no one feels it more than No. 99.