By now, the New York Yankees fans have gone from confused to frustrated to confused again. Does this team really think they can do it without making any major moves this winter? Christmas has come and gone, and the calendar year has one day left, and even then, no big moves, apart from the Grisham and the Amed Rosario move recently.

So when Hal Steinbrenner was talking about a “budget,” was that really it? Are the Yankees not willing to spend? For now, the Yankees are drifting. Cashman has spent the winter pushing back on inflated asking prices and being unwilling to overpay in trades and free agency. That restraint might sound sensible on paper, but in practice, it has left the roster frozen in place.

Players like Trent Grisham are now caught in the middle of uncertainty! And Clint Frazier summed it up best in his Life After the Show podcast—for him, Trent Grisham will be under major pressure if the Yankees don’t end up signing others.

The former Yankee said, “If Trent Grisham is the biggest signing that the Yankees have this offseason, then a lot of pressure is on a few people with the Yankees next year. One, the pressure is on Trent Gisham, and two, the pressure is on Brian Cashman and whoever else told them to put that deal on the table.”

Frazier questioned one thing—can Trent Grisham really produce like a $22 million player if this is where the Yankees stop making any move? Now, Grisham’s 2025 season was a breakout year for him. Thirty-four home runs, an .811 OPS, and clutch moments made him a fan favorite. But dig a little deeper, and then the details get a little murkier.

Grisham’s defensive metrics have slipped, and his Outs Above Average has dropped to -2 after years of elite play. It does look like Grisham may have traded some glove for bat, too, and while the power surge was there, it’s fair to wonder how repeatable that thing is. More than a third of his career home runs came in one season after all.

The fact is that if the Yankees added another outfielder like Cody Bellinger or Kyle Tucker, the outfield logjam would intensify and Jasson Domínguez would get squeezed. If they don’t, then Grisham becomes a highlight by default and not by design. Baseball Reference now projects a solid but great follow-up, close to 22 homers, then 34, which is fine but not as per expectations.

That’s the real crisis—not Grisham himself but the indecision around him. The Yankees have a lot of questions unanswered.

Yankees hold major leverage as Cashman waits out on Cody Bellinger 

The New York Yankees are playing a dangerous but calculated game with Scott Boras this offseason. And for once, it feels like they are winning. While the fans are restless for clarity, Cashman made one thing clear—he is not bidding against himself for Cody Bellinger.

Yes, the Yankees want Bellinger in pinstripes; they badly do. But they have also drawn a firm line when it comes to the contract length. They are fine to wait and watch till the market cools. And in an off-season that was supposed to explode for Boras clients, the silence has been telling, and the Yankees know this.

Bellinger came into the winter expecting a long-term payday, something in the seven-year range that would carry him well into his mid-30s. That deal has not materialized, but according to Jon Heyman of the New York Post, the Yankees seem somewhat confident they can retain Bellinger. That confidence comes from leverage.

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The main sticking point seems to be the years. Boras wants a max term, and the Yankees don’t, and as Heyman noted, Bellinger might have to settle for six years instead of seven. To a front office that’s been burned earlier by contracts, it’s a meaningful win.

The Yankees are also because Bellinger fits well in the roster. He was reborn in the Bronx last season, and he took full advantage of the short porch in right field and posted his best numbers since his MVP days.

He was a steady presence behind Aaron Judge, and this made him exactly what this lineup needed. Cashman knows it, Boras knows it, and now it’s a matter of who blinks first.